CLEVELAND, Ohio – If the 1980s was defined by the boom of pop music, the rise of hip hop, the dominance of glam metal and the evolution of dance music, the 1990s was all about how artists could reinvent those genres.
All you have to do is follow the No. 1 hits. Music seemed to defy categorization throughout the 1990s. Whether you were rapping, rocking, singing or dancing, it all fell under one umbrella: Popular music.
The hits from the decade run the gamut of flavors of the week to dominant artists that had the golden touch. Some of the names and the titles you’ll remember. Others you won’t? But all it takes is one note or hook and the memories come back.
First, the rules. In ranking the No. 1 hits of the 1990s we’re dealing with songs that went to No. 1 on the Billboard Hot 100 chart. The songs did not have to be released in the 1990s, but they had to go to No. 1 for the first time in the decade.
It wasn’t easy and, as always, this is just one person’s opinion. But here’s how we ranked the 140 songs that went to the top of the mountain during the decade:
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140. Timmy T - “One More Try”
When: March 23, 1991
Weeks on top: 1
We might as well start with the song on this that’s the biggest head-scratcher. There are hits more spectacularly awful than Timmy T’s “One More Try.” But none quite as mundane. In retrospect, it’s unfathomable that “One More Try” was a massive hit let alone in the United States, but on a global scale as well. It helps that it was 1991, not too far removed from the 1980s' obsession with synthesizers in pop music. But that doesn’t explain it unseating Mariah Carey’s “Someday” from the top spot that March. Timmy T’s breakup song may arguably be the least interesting song to ever hit No. 1, regardless of the decade.
139. Silk - “Freak Me”
When: May 1, 1993
Weeks on top: 2
As a protege of Keith Sweat, Silk had its appeal. The group also has some very good songs. But “Freak Me,” Silk’s biggest hit, is not one of them. The soft voice contrasted by a ton of over-singing (not to mention the all too literal lyrics) may have been sexy in 1993. But there’s no way to listen to this now without cringing a lot.
138. Will Smith featuring Dru Hill & Kool Moe Dee - “Wild Wild West”
When: July 24, 1999
Weeks on top: 1
“Wild Wild West” is the perfect storm of a terrible song. It’s attached to an awful movie of the same name. It samples and ruins a classic song (Stevie Wonder’s “I Wish”), features an aging rapper and it has Sisqo.
137. Bryan Adams - “Have You Ever Really Loved A Woman”
When: June 3, 1995
Weeks on top: 5
By the time this list is over, you’ll think I hate Bryan Adams. I do not. Adams has some great songs throughout the 1980s. His cover of “Summer of ’69” is fantastic, while “Heaven” might be the peak of schmaltzy Eighties power-pop. Then the 1990s came and Adams' career revolved around movie soundtracks and essentially creating the same song over and over again. Nothing hurts the ears more than “Have You Ever Really Loved a Woman” from the “Don Juan DeMarco" soundtrack. The track paints Adams, the ultimate Canadian white guy crooning over a Spanish melody, as the lothario he certainly is not.
136. Meat Loaf - “I’d Do Anything for Love (But I Won’t Do That)”
When: Nov. 6, 1993
Weeks on top: 5
Meat Loaf’s “I’d Do Anything for Love” is so over the top ridiculous that it almost had to reach No. 1 to justify its existence. That doesn’t mean it’s good (it isn’t). But it truly is a song like no other that came at the exact right moment, sandwiched between massive hits from Janet Jackson and Mariah Carey.
135. Tommy Page - “I’ll Be Your Everything”
When: April 14, 1990
Weeks on top: 1
It’s time to ruin the prom memories of Gen-Xers by telling them that Tommy Page’s “I’ll Be Your Everything” is flat out boring. Page had the look and the “New Kids on the Block” knockoff voice. But “I’ll Be Your Everything” sounds like the NKOTB knockoff it is, considering it was written by Page, Jordan Knight and Danny Wood.
134. Los Del Rio - “Macarena (Bayside Boys Mix)”
When: Aug. 3, 1996
Weeks on top: 14
It’s not going to surprise anyone to see “Macarena” on the backend of this list. But let’s talk about how huge of a song it was. It spent a whopping 14 weeks at No. 1. Only one song (“One Sweet Day”) had a longer run. It wouldn’t be that hard to see “Macarena” taking off if it came out in during TikTok era.
133. Right Said Fred - “I’m Too Sexy”
When: Feb. 8, 1992
Weeks on top: 3
While mocking all the posing going on around them, two gym rats from London come up with the idea to make a dance-pop song that becomes an international phenomenon. You can’t make something like that up. Nor. can you make up a lyric like “I’m too sexy for my cat.” At least the song could poke fun at itself.
132. Stevie B - “Because I Love You (The Postman Song)”
When: Dec. 8, 1990
Weeks on top: 4
“Because I Love You" is one of the most uncool No. 1 hits of all time. And not just because adding “The Postman Song” to the title is a stupid way to make it seem more distinct. At one point towards the end of the song, Stevie B makes the poor choice to sing about himself in the third person (“And Stevie B will always be around…”). Sorry, Stevie, you won’t.
131. Paula Abdul & The Wild Pair - “Opposites Attract”
When: Oct. 6, 1990
Weeks on top: 3
How do you make Paula Abdul’s “Opposites Attract,” a song that sounds like it was ripped from the Mickey Mouse Club, even cornier? You put an animated, rapping cat in the video.
130. Bryan Adams, Rod Stewart & Sting - “All For Love”
When: Jan. 22, 1994
Weeks on top: 3
At some point in the early 1990s, Bryan Adams and producer Mutt Lange decided they wanted to see how many rock stars they could embarrass on one track. Enter “All For Love,” which was for the “The Three Musketeers” soundtrack (because, of course, it was). Adams tapped Rod Stewart and Sting for the power-ballad, a regretful choice considering the vocal suits none of them.
129. Vanilla Ice - “Ice Ice Baby”
When: Nov. 3, 1990
Weeks on top: 1
Let’s not pretend that Vanilla Ice’s “Ice Ice Baby” wasn’t the coolest thing going in 1990. Ice was everything MC Hammer was, only white, which made him the culture-jacker to end all culture jackers. Robert Van Winkle has done everything he can to distance himself from the song, going as far as to record a rock version that will all but kill your brain cells.
128. UB40 - “(I Can’t Help) Falling in Love with You”
When: July 24, 1993
Weeks on top: 7
UB40′s cover of an Elvis classic is both downright awful and pure genius. There’s something smart about in theory: Take one of the best-written love songs of all time and give it a dance-pop beat at a time when the genre was taking off. But to realize just how wrong it is, go back and listen to Elvis' version - a simple, moving love song that was played at thousands of weddings before UB40 butchered it.
EastWest
127. Snow - “Informer”
When: March 13, 1993
Weeks on top: 7
A song about being ratted out to cops written and delivered by a white guy…and he’s from Canada. From a street-cred standpoint, this shouldn’t have been popular. But the early 1990s was a different universe and it doesn’t matter that you can’t understand a single word other than “informer.”
126. Wilson Phillips - “Release Me”
When: Sept. 15, 1990
Weeks on top: 2
Every Wilson Phillips single walks a fine line between a great pop song and a sugary sweet mess. “Release Me” falls more on the latter. To be clear, every Wilson Phillips song has a great moment. “Release Me’s” happens with “Come on baby, come on baby…” But it takes a painful 90 seconds to get there!
125. R. Kelly & Céline Dion - “I’m Your Angel”
When: Dec. 5, 1998
Weeks on top: 6
We chose to separate personal scandals from the quality of these songs. But it’s hard not to cringe when you hear R. Kelly singing “I’m Your Angel.” From a music standpoint, the song is pretty unexceptional, especially compared to R. Kelly’s other tracks that didn’t reach No. 1 (“I Believe I Can Fly” peaked at No. 2).
124. Glenn Medeiros featuring Bobby Brown - “She Ain’t Worth It”
When: July 21, 1990
Weeks on top: 2
Glenn Mederios' “She Ain’t Worth It” isn’t much more than a generic new jack swing song (maybe, the most generic of them all). What boosted it out of obscurity (where it belonged) was its Bobby Brown feature. The song arrived on the heels of Brown’s incredible late 1980s solo run.
123. Sweet Sensation - “If Wishes Came True”
When: Sept. 1, 1990
Weeks on top: 1
Probably one of the lesser-known No. 1 hits on this list and for good reason. Sweet Sensation was known for its dance music in the 1980s. Thus, “If Wishes Came True” arrived out of nowhere, owning the charts for one week in 1990. The overly dramatic pop-rock song feels like something Debbie Gibson passed on.
122. Mr. Big - “To Be With You”
When: Feb. 29, 1992
Weeks on top: 3
Not even a year after Extreme reached the top of the Billboard Hot 100 with its acoustic ballad “More Than Words,” another hard rock group Mr. Big bit the same formula for “To Be With You.” The song’s singalong chorus is fun after a few beers. The rest of it doesn’t carry too much value.
121. Nelson - “(Can’t Live Without Your) Love And Affection”
When: Sept. 29, 1990
Weeks on top: 1
Nelson’s “(Can’t Live Without Your) Love and Affection” is about a crush on Cindy Crawford. Though, sadly she wasn’t featured in the music video. The track is a perfectly fine glam metal love song with a catchy hook. Though, it’s cheese factor can’t help but make you thankful Nirvana eventually showed up to do away with these kinds of tunes.
120. Madonna - “This Used To Be My Playground”
When: Aug. 8, 1992
Weeks on top: 1
“This Used To Be My Playground” is a testament to just how big Madonna was in the 1990s. While some fans (especially those who love Penny Marshall’s excellent “A League of Their Own”) have a special place in their hearts for it, “This Use To Be My Playground” is the ultimate Madonna snooze fest.
119. Paula Abdul - “The Promise of a New Day”
When: Sept. 14, 1991
Weeks on top: 1
If you were asked to name Paula Abdul’s No. 1 hits, “The Promise of a New Day” is probably the one you’d forget. It’s the most generic of her early 1990s dance tunes and was riding the success of her ultimate ballad “Rush Rush."
118. Michael Bolton - “When A Man Loves A Woman”
When: Nov. 23, 1991
Weeks on top: 1
You have to give Michael Bolton credit. The guy can sing the heck out of a song. His cover of “When a Man Loves a Woman” is nothing special and lacks the raw emotion of Percy Sledge’s original. But listeners latched onto it and Bolton’s flowing hair at the start of the 1991 holiday season.
117. Wilson Phillips - “You’re in Love”
When: April 20, 1991
Weeks on top: 1
Everything about this song will annoy you, especially if you’re in a bad mood. Not only is it about love. It’s also about being okay that the person you’re in love with has fallen for someone else (Because that’s a thing). And yet, Wilson Phillips just knows how to get to your heart with a big chorus.
116. Surface - “The First Time”
When: Jan. 26, 1991
Weeks on top: 2
“The First Time” is a solid love song that’s beautifully sung. It just doesn’t really go anywhere dynamic.
115. Divine - “Lately”
When: Nov. 28, 1998
Weeks on top: 1
Divine’s “Lately” is a gospel song masquerading as an R&B jam. And it’s is all about a hook that invades your ears with its layered vocals.
114. R. Kelly - “Bump n' Grind”
When: April 9, 1994
Weeks on top: 4
R. Kelly was always a smart songwriter. Whereas other 1990s songs about sex played things too literal (See: No. 139), Kelly knew how to make things suitable for the mainstream. Not only could he put together a heck of a melody, but he could also disguise his R-rated subject matter in a phrase like “Bump n' Grind” and a slew of generic lyrics.
113. Londonbeat - “I’ve Been Thinking About You”
When: April 13, 1991
Weeks on top: 1
Topping the charts in 1991, Londonbeat’s hit dance-pop song was one of the first mainstream pop songs to bring house music to the mainstream. In that sense, it’s classic and quite groundbreaking, even if the lead vocal is a bit annoying.
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112. Puff Daddy & Faith Evans featuring 112 - “I’ll Be Missing You”
When: June 14, 1997
Weeks on top: 11
Leave it to Puff Daddy to flip a song about stalking into a goodbye song for his late friend. The classic rock world had to be made as heck at this one. Mainly because it was EVERYWHERE. “I’ll Be Missing You,” which samples The Police’s “I’ll Be Missing You,” stayed on top of the charts for 11 weeks. Part of that was the music world still mourning the loss of The Notorious B.I.G. But don’t overlook that while Puff’s rhymes are just meh, Faith Evans' heartfelt performance on the chorus pushes the song over the top.
111. Whitney Houston - “All the Man That I Need”
When: Feb. 23, 1991
Weeks on top: 2
One of the weaker singles of Whitney Houston’s career comes from her divisive album “I’m Your Baby Tonight.” Still, fans ate up “All the Man That I Need” in no small part because it brought them back to the ballads that made Houston a star. And while the verses are overly subdued, Houston delivers the goods on the chorus.
110. Maxi Priest - “Close To You”
When: Oct. 6, 1990
Weeks on top: 1
The fall of 1990 was like musical chairs on the Billboard Hot 100. Six songs each spent just one week on top. That list included Maxi Priest’s “Close To You,” which is about the mellowest new jack swing song you’ll ever hear fused with Maxi Priest’s reggae style.
109. Mariah Carey - “I Don’t Wanna Cry”
When: May 25, 1991
Weeks on top: 2
Of all Mariah Carey’s No. 1 songs, “I Don’t Wanna Cry” may be the most ordinary, utilizing the Spanish guitar sound that was all the rage in the soul music of the early 1990s. Yet, that doesn’t stop Carey from rescuing the song with an amazing vocal as always.
108. Monica - “The First Night”
When: Oct. 3, 1998
Weeks on top: 5
Listening to it now, Monica’s “The First Night” may not feel like a song that topped the charts for a total of five weeks. But back in 1998, its hip-hop soul vibe fit right in with the times. It was also a moment where the industry had to start taking Jermaine Dupri seriously as one of its biggest and best hitmakers.
107. Puff Daddy featuring Mase - “Can’t Nobody Hold Me Down”
When: March 22, 1997
Weeks on top: 6
March 1997 was a bittersweet time for Puff Daddy. His single “Can’t Nobody Hold Me Down” went to No. 1, but just weeks after the death of The Notorious B.I.G. The song was yet another example of Puffy’s ability to turn the old into new again, sampling a few classic songs, most notably Grandmaster Flash and the Furious Five’s “The Message.” For hip-hop diehards, that may have been a form of musical sacrilege. But Puff just kept counting the money.
106. Boyz II Men - “4 Seasons of Loneliness”
When: Oct. 4, 1997
Weeks on top: 1
Of the handful of No. 1 songs Boyz II Men released in the 1990s, “4 Seasons of Loneliness” is the most forgettable. But it’s still pretty darn good. A bit of trivia: Not only was the song B2M’s final chart-topper. It was also the last No. 1 single on the Billboard Hot 100 released on Motown Records.
105. James Ingram - “I Don’t Have the Heart”
When: Oct. 20, 1990
Weeks on top: 1
Not the most memorable song to hit No. 1 in the early 1990s. But James Ingram’s “I Don’t Have the Heart” is a could sing with the best of his generation. The song was the Akron native’s lone No. 1 as a solo artist coming seven years after he topped the charts alongside Patti Austin on “Baby, Come to Me.”
104. Brandy - “Have You Ever?”
When: Jan. 16, 1999
Weeks on top: 2
By the late 1990s, Diane Warren and David Foster’s pop songs – even the good ones – started to blend. “Have You Ever?” is no different. Still, there’s something to be said for being able to write a hit song and make it look easy. Fortunately, Brandy can sing about anything and make it sound exceptional.
103. Color Me Badd - “All 4 Love”
When: Jan. 25, 1992
Weeks on top: 1
“All 4 Love” is nothing more than Color Me Badd doing its version of a 1960 R&B/doo-wop song. And it works. The group’s harmonies were never complex. But they find their niche on a breezy track that was just catchy enough to kick Michael Jackson’s “Black or White” out of the top spot at the beginning of 1992.
102. Mariah Carey - “Love Takes Time”
When: Nov. 10, 1990
Weeks on top: 3
To some, “Love Takes Time” may always be remembered as the song Mariah Carey released after “Vision of Love.” But you could argue it does just as great of a job showing off Carey’s otherworldly vocals. Is it the showstopper “Vision of Love” is? No. But what is?
101. Céline Dion - “The Power Of Love”
When: Feb. 12, 1994
Weeks on top: 4
"Jennifer Rush’s original “The Power of Love” was huge in the UK back in 1984. So big, you had to bring you’re A-game when covering it. Enter Celine Dion. The pop song isn’t all that unique. But with David Foster producing the cover and Dion singing the heck out of it, how could it not go to number one right before Valentine’s Day 1994?
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100. Next - “Too Close”
When: April 25, 1998
Weeks on top: 5
You couldn’t get a dancefloor in the late 1990s without hearing Next’s “Too Close.” That’s appropriate since the song is about a man getting, ahem, “excited” while dancing up against a woman. It’s likely that little bit of naughty that pushed it to the top of the charts.
99. Janet Jackson - “Again”
When: Dec. 11, 1993
Weeks on top: 2
“Again” represents the most straightforward ballad of Jackson’s career. And the most popular. While the song was featured on her album “Janet,” it is best remembered as the closing tune in her film “Poetic Jackson,” co-starring Tupac Shakur.
98. Mariah Carey - “Someday”
When: March 9, 1991
Weeks on top: 2
Even when Mariah Carey does basic dance-pop, she still kills it. The first two singles of her career were powerhouse ballads. Moving into the realm of dance music didn’t slow things a bit. “Someday” became Carey’s third straight No. 1 to start her career.
97. Gloria Estefan - “Coming Out of the Dark”
When: March 30, 1991
Weeks on top: 2
“Coming Out of the Dark” is the most moving song of Gloria Estefan’s excellent career. It’s the first single she released after a near-fatal accident. Estefan’s back was nearly broken for good. She turned the near-tragedy into a soaring pop anthem that would become her third No. 1 hit in the U.S.
96. George Michael & Elton John - “Don’t Let the Sun Go Down on Me”
When: Feb. 1, 1992
Weeks on top: 1
“Don’t Let The Sun Go Down On Me” has a unique history. Elton John originally recorded the song for his 1974 album “Caribou.” It went all the way to No. 2. John then performed it with George Michael at Live Aid in 1985. Michael’s cover of the song became massively popular, culminating with the two performing it together at Wembley Arena in 1991. The live recording was released as a single that eventually went to No. 1.
95. Roxette - “It Must Have Been Love”
When: June 16, 1990
Weeks on top: 2
The Billboard Hot 100 was a weird place at the start of the 1990s. Looking back, it took about a year to get to the music that represents what we consider the core pop sound of the decade. Thus, those first 12 months are full of songs like Roxette’s “It Must Have Been Love” that is so Eighties, it’s hard to fathom until you realize the song was first released in 1987. Roxette re-released it for the soundtrack for “Pretty Woman." it got so big the track was redone in country, Spanish and classical versions.
94. Mariah Carey - “My All”
When: May 23, 1998
Weeks on top: 1
Mariah Carey was in another phase of cruise control with the singles from her hit album “Butterfly.” While her music was moving in more of an urban direction, she could still nail the ballads. As proof, she released “My All” as the final single from the album, closing things out with yet another No. 1.
93. Alannah Myles - “Black Velvet”
When: March 24, 1990
Weeks on top: 2
A forgotten country-rock gem from the start of the 1990s. Alannah Myles brings swagger to her No. 1 hit “Black Velvet.” The key is the way she sings the song’s title. It was enough to hook listeners for two weeks in March 1990.
92. Mariah Carey - “I’ll Be There”
When: June 20, 1992
Weeks on top: 2
As the story goes, Mariah Carey’s record label wanted to dispel any notions she couldn’t sing in a live setting. So they booked her on “MTV Unplugged” where she (along with Trey Lorenz) decimated all with a cover version of The Jackson 5 classic “I’ll Be There.” Yep, she could sing.
91. Taylor Dayne - “Love Will Lead You Back”
When: April 7, 1990
Weeks on top: 1
If people thought Taylor Dayne had peaked with her collection of singles from the late 1980s, they were wrong. Dayne had at least one megahit left in her with “Love Will Lead You Back.” Credit to Dayne for nailing the vocal. But the true credit goes to yet another beautifully written gem from Diane Warren, who would go on to dominate the Nineties.
90. K-Ci & JoJo - “All My Life”
When: April 4, 1998
Weeks on top: 3
For anyone listening to the radio in 1998, K-Ci & JoJo’s “All My Life” was so overplayed you probably never want to hear it again. Yet to step out of the shadow of their previous group Jodeci, the two brothers would finally hit the mark with the third single from their debut. “All My Life” would go platinum and have a better chart run than anything Jodeci ever released.
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89. Mariah Carey featuring Jay-Z - “Heartbreaker”
When: Oct. 9, 1999
Weeks on top: 12
Mariah Carey’s final No. 1 of the 1990s captures a moment in time. The sample-heavy “Heartbreaker” merges Carey’s pop-turned-urban sound with a guest appearance from the hottest rapper of the time...a guy named Jay-Z.
88. Color Me Badd - “I Adore Mi Amor”
When: Sept. 21, 1991
Weeks on top: 2
Color Me Badd’s “I Adore Mi Amor” comes across as not much more than a glorified vocal exercise a group does before heading into the studio. That’s probably part of its appeal. Simple and to the point, the love song from the “I Wanna Sex You Up” guys even throws in a bit of Spanish to give it some global appeal. Dream on, dream away.
[Write’s Note: This is where I have to acknowledge that No. 1 hits are often about timing. The list of songs, like Color Me Badd’s “I Wanna Sex You Up,” that didn’t go to No. 1 is astonishing. It includes LeAnn Rimes' “How Do I live,” Jewel’s “Foolish Games/You Were Meant For Me,” Shania Twain’s “You’re Still the One” and so many others.]
87. Janet Jackson - “Black Cat”
When: Oct. 27, 1990
Weeks on top: 1
Anyone who doesn’t view Janet Jackson as a rock star should take another listen to “Black Cat.” At a time when rock music was being pushed off the mainstream charts by pop tunes, Jackson’s hard rock anthem ruled over them all during the fall of 1990.
86. The Heights - “How Do You Talk To An Angel”
When: Nov. 14, 1992
Weeks on top: 2
Before he played the lovable boyfriend turned villain Ray Pruit on “Beverly Hills, 90210,” Jamie Walters was a music star. Walters sang lead on “How Do You Talk To An Angel,” a song that served as the backbone for the series Fox “The Heights,” which centered on a fictional band also called The Heights (confusing, right?). The show lasted just one season. But the song went to No. 1.
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85. Kris Kross - “Jump”
When: April 25, 1992
Weeks on top: 8
By today’s standards of mumble rap, two young guys coming up with a gimmick of wearing their clothes backward seems mild. The magic of Kris Kross was the duo had one heck of a song on their hands. “Jump” matches Kris Kross' aggressive rhymes with a hip-hop beat that bites West Coast G-funk. The song stood at No. 1 for two months and served as the breakthrough for producer Jermaine Dupri.
84. Mariah Carey - “Hero”
When: Dec. 25, 1993
Weeks on top: 4
This is probably too low for “Hero.” In many ways, it feels like the song Mariah Carey was born to sing. Carey would have more dynamic hits in the years that followed. But “Hero” remains her most universal song in terms of theme.
83. Karyn White - “Romantic”
When: Nov. 2, 1991
Weeks on top: 1
Karyn White had about as good of a run as you can have with singles in the late 1980s/early 1990s. Her songs “Superwoman,” “The Way You Love Me” and “Secret Rendezvous” all performed well on the charts. But it was 1991′s “Romantic” that marked the peak of White’s career. The song is built in the mold of Janet Jackson’s classics of the time (produced by Jimmy Jam and Terry Lewis) and just as catchy.
82. Vanessa Williams - “Save the Best for Last”
When: March 21, 1992
Weeks on top: 5
These days, people know Vanessa Williams as an actress. But she has quite the backstory as a dual-threat. Williams was forced to give up her crown as Miss America 1984 after nude photos were published of her. However, she earned redemption with a solid music career that peaked with this 1992 ballad that earned multiple Grammy nominations.
81. Bryan Adams- “(Everything I Do) I Do It for You”
When: July 27, 1991
Weeks on top: 7
“(Everything I Do) I Do It for You” ruled the charts for an excruciating seven weeks back in 1991. Written for the soundtrack to the awful Kevin Costner film “Robin Hood: Prince of Thieves,” Adams' massive hit was unrelentingly emotional. Talk about vapid. But that didn’t stop millions of people from loving it.
80. Boyz II Men - “On Bended Knee”
When: Dec. 3, 1994
Weeks on top: 6
Proof that in the 1990s, only Boyz II Men could top Boyz II Men. The group’s single “I’ll Make Love to You” spent a record-tying 14 weeks atop of the Billboard Hot 100 chart. The song that booted it from the top spot was also from Boyz II Men. The breakup ballad “On Bended Knee” was another huge hit for the group, ruling the charts for a non-consecutive total of six weeks.
79. Whitney Houston - “I’m Your Baby Tonight”
When: Dec. 1, 1990
Weeks on top: 1
Whitney Houston doing new jack swing? After two monster albums in the 1980s driven by ballads and dance-pop, Houston’s team looked to give her a modern sound on her third effort “I’m Your Baby Tonight.” The title track was certainly surprising in its harder sound. But it worked, giving Houston yet another No. 1.
78. SWV - “Weak”
When: July 10, 1993
Weeks on top: 2
SWV had already scored hits with “Right Here” and “I’m So Into You.” But it was the third single from the group’s album “It’s About Time” that went to No. 1. The difference was a shift from new jack swing to a more traditional R&B ballad perfectly written by Brian Alexander Morgan to capture the feeling of young love.
77. Enrique Iglesias - “Bailamos”
When: Sept. 4, 1999
Weeks on top: 2
When he arrived in mainstream American circles, Enrique Iglesias was seen as two things: The son of Julio Iglesias and a Ricky martin knockoff. The former was true, but the latter was an underestimation of how talented Enrique was. His run of hits would push him past anything Martin did, beginning with “Bailamos,” which served as the ultimate example of Latin pop as a force heading into the 21st century.
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76. Jon Bon Jovi - “Blaze Of Glory”
When: Sept. 8, 1990
Weeks on top: 1
If “Blaze of Glory” sounds a lot like “Wanted Dead or Alive,” it’s supposed to. Jon Bon Jovi wrote the song for the “Young Guns II” soundtrack only after being asked if Bon Jovi’s western-themed hit could be used in the film. Despite officially being a Jon Bon Jovi solo song, “Blaze of Glory” remains one of the most popular songs in Bon Jovi’s repertoire.
75. Monica - “Angel of Mine”
When: Feb. 13, 1999
Weeks on top: 4
Both Brandy and Monica benefitted greatly from the success of “The Boy Is Mine.” But they both deserve credit for continuing to sing great songs. In Monica’s case, one of her other No. 1 hits was a cover of British girl group Eternal’s 1997 single. But Monica’s version, which capitalized on her star power and fine-tuned production by Rodney Jerkins, proved the perfect mix of R&B and pop to conquer the charts for a month in 1999.
74. Céline Dion - “Because You Loved Me”
When: March 23, 1996
Weeks on top: 6
A year or so before she sang the theme to “Titanic,” Celine Dion became a pop star with another song from a movie. “Because You Loved Me” was written (of course) by Diane Warren and produced (of course) by David Foster for the film “Up Close and Personal,” which made roughly $2 billion less at the box office than “Titanic."
73. Amy Grant - “Baby Baby”
When: April 27, 1991
Weeks on top: 2
It might seem less relevant these days. But back in the late 1980s/early 1990s, Amy Grant was the blueprint for an artist going from Christian music to mainstream pop. And she made it seem rather easy with “Baby Baby,” a song with all the production bells and whistles of the era’s best pop songs that earned a Grammy nomination for Song of the Year.
72. TLC - “Unpretty”
When: Oct. 9, 1999
Weeks on top: 3
Not only is “Unpretty” one of TLC’s most inspirational anthems. It’s also a tribute to the group’s range. “Unpretty,” co-written by T-Boz and producer Dallas Austin, is an alternative rock song whose release would have been shocking had the track not been so catchy.
71. Madonna - “Take A Bow”
When: Feb. 25, 1995
Weeks on top: 7
No other song in Madonna’s catalog sounds like “Take A Bow,” a song crafted by Babyface (who also sings backing vocals) that moved her into the realm of R&B. The collaboration worked wonders, thanks in part to a sensual video featuring Madonna’s fictional (as far as we know) love with a matador that sat in heavy rotation on MTV.
70. Michael Jackson - “You Are Not Alone”
When: Sept. 2, 1995
Weeks on top: 1
You can tell by its intro “You Are Not Alone” was written by R. Kelly. The entire production is done in his signature style. But it’s Jackson who took the song to No. 1 on the strength of one of the best vocals of his career and the media hype surrounding the drama going on in the pop star’s personal life.
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69. Michael Bolton – “How Am I Supposed to Live Without You”
When: Jan. 20, 1990
Weeks on top: 3
Technically, the first No. 1 single of the 1990s was Phil Collins' “Another Day in Paradise.” But it’s consecutive run began in the 1980s. Thus, it didn’t qualify for this list. The first new chart-topper of the decade was Michael Bolton’s “How Am I Supposed to Live Without You.” It’s easy to poke fun at Bolton and his golden locks. But the man could sing. “How Am I Supposed to Live Without You” (a song originally intended for Air Supply) pushed Bolton, known until then solely as a stellar songwriter, into the spotlight as a performer.
68. Hi-Five - “I Like the Way (The Kissing Game)”
When: May 18, 1991
Weeks on top: 1
You can be excused for not remembering Hi-Five and R&B group overshadowed by the new jack swing era it was successful in. But there’s no denying the group’s infectious hit “I Like the Way (The Kissing Game).” It’s also probably not surprising to learn the track was co-written and produced by Teddy Riley, the king of new jack swing.
67. George Michael - “Praying for Time”
When: Oct. 13, 1990
Weeks on top: 1
To this day, you could make the case that George Michael is underrated as a vocalist. But it’s songs like “Praying for Time” that prove he’s one of the greatest singers of all time. The song was Michaels' first single of the 1990s, establishing his star power in a new decade.
66. Montell Jordan - “This Is How We Do It”
When: April 15, 1995
Weeks on top: 7
Hip hop label Def Jam sure knew how to break into the R&B market. The record company’s first release in the genre was “This Is How We Do It,” a party-starter by Montell Jordan that rode a sample of Slick Rick’s “Children’s Story” to platinum status and the top of the Billboard Hot 100 for seven weeks.
65. Peabo Bryson & Regina Belle - “A Whole New World”
When: March 6, 1993
Weeks on top: 1
Disney released several big songs from its 1990s golden run of films. But only one of them went to No. 1. That honor goes to “A Whole New World” from “Aladdin.” From a nostalgia standpoint, it’s hard not to prefer the version performed in the film. But the chart version was a duet by Peabo Bryson (the go-to for Nineties Disney soundtracks) and Regina Belle.
64. Toni Braxton - “You’re Makin' Me High” / “Let It Flow”
When: July 27, 1996
Weeks on top: 1
Released on a double A-side with “Let It Flow,” “You’re Makin' Me High” upstaged its counterpart, which was included on the “Waiting to Exhale” film soundtrack. Known for her ballads, Braxton tapped into dance and hip-hop markets with the bouncy and sensual “You’re Makin' Me High.”
63. Elton John - “Candle in the Wind ’97”/"Something About the Way You Look Tonight"
When: Oct. 11, 1997
Weeks on top: 14
A huge part of the love affair people had with “Candle in the Wind 1997” had to do with the tragic loss of Princess Diana. Bernie Taupin and Elton John re-wrote and re-recorded their beautiful ballad (originally made in 1973) in tribute to the Princess of Wales. It was released as a double A-side single with “Something About the Way You Look Tonight” and went on to become the second-best-selling physical single in music history.
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62. Savage Garden - “Truly Madly Deeply”
When: Jan. 17, 1998
Weeks on top: 2
Some people are just great at writing perfect pop songs. For a short stretch in the 1990s, you could count the members of Savage Garden among them. The Australian duo’s crowning achievement is “Truly Madly Deeply,” a chart-topper that epitomizes the breezy sounds of Nineties mainstream pop.
61. Janet Jackson - “Together Again”
When: Jan. 31, 1998
Weeks on top: 2
Janet Jackson’s moving song about losing a friend certainly would have made an excellent ballad. But Jackson, along with producers Jimmy Jam and Terry Lewis, decided to flip it into a dance-pop and house song, giving it universal appeal and spreading her message on a global scale.
60. Mariah Carey & Boyz II Men - “One Sweet Day”
When: Dec. 2, 1995
Weeks on top: 16
That number above is not a typo. “One Sweet Day” brought together two of the biggest hitmakers of the decade. The results were record-breaking. “One Sweet Day” sat atop the Billboard Hot 100 for 16 weeks. This, in a pre-Internet, pre-streaming era when you had to go to love a song enough to go the record store to purchase singles.
59. Whitney Houston - “Exhale (Shoop Shoop)”
When: Nov. 25, 1995
Weeks on top: 1
Whitney Houston followed up the massive success of “The Bodyguard” with another film and soundtrack. This time around it was “Waiting to Exhale.” It’s hit single “Exhale (Shoop Shoop)” was seen as the sound of Houston maturing. Written by Babyface, the blissful song still made way for Houston’s beautiful voice, only it came with a lighter, perhaps, more inviting touch.
58. Destiny’s Child - “Bills, Bills, Bills”
When: July 17, 1999
Weeks on top: 1
“Bills, Bills, Bills” marked the beginning of Destiny’s Child’s run. It also confirmed that the blueprint for girl groups moving forward had been established by TLC. Credit the producer/writer team of Kevin Briggs and Kandi Burruss, who also wrote “Scrubs,” for the catch “Bills, Bills, Bills,” which (shocker) contains a reference to a man being a scrub.
57. Ini Kamoze - “Here Comes the Hotstepper”
When: Dec. 17, 1994
Weeks on top: 2
You have to be of a certain age to recall Ini Kamoze’s “Here Comes the Hotstepper” ruling the charts. And even then, it’s still kind of a shock. Jamaican dancehall artist Kamoze was far from a household name. But mixing samples of a few funk and hip hop songs, his song offered an unforgettable groove. Sampling Wilson Pickett’s “Land of 1000 Dances” for the “na, na, na, na, na…” on the hook was the icing on the cake.
56. Mariah Carey - “Honey”
When: Sept. 13, 1997
Weeks on top: 3
“Honey” was the introduction of a new Mariah. From a look standpoint, she seemed liberating, showing off as much skin as she ever had in the iconic music video. Sonically, she’s moved into urban music territory thanks to producer Puff Daddy, who shaped “Honey” in the mold of the huge hits coming out of his Bad Boy Records at the time.
55. Usher - “Nice & Slow”
When: Feb. 14, 1998
Weeks on top: 2
Usher’s first handful of singles (released before he reached puberty) didn’t make much of a dent. Then came the release of his album “My Way” and the one-two punch of “You Make Me Wanna…” and “Nice & Slow.” There isn’t a 1990s R&B fan who doesn’t know the words to both. The latter reached No. 1 appropriately on Valentine’s Day and all it took is Usher spelling out his full name for listeners.
54. Ace Of Base - “The Sign”
When: March 12, 1994
Weeks on top: 6
Do you want to have an interesting debate with a 90s baby? Ask them what the best of Ace of Base song is. I’m on team “All That She Wants.” But the deciding factor could be that only one of them went all the way to No. 1. “The Sign” is the epitome of what Ace of Base was all about. Sweden’s greatest musical import since ABBA brought pop-savvy melodies to dance music. Ace of Base’s influence can still be felt today among some of the biggest pop stars in the world, including Lady Gaga, Robyn and Katy Perry.
53. Seal - “Kiss from a Rose”
When: Aug. 26, 1995
Weeks on top: 1
Seal’s mesmerizing “Kiss from a Rose” can lay claim to two soundtracks. It was originally included in the film “The NeverEnding Story III” in 1994. No one cared about the song or the movie. When “Kiss from a Rose” was re-released a year later with the “Batman Forever” soundtrack, it exploded, going on to dominate the 1996 Grammys with Record and Song of the Year wins.
52. Jennifer Lopez - “If You Had My Love”
When: June 12, 1999
Weeks on top: 5
Jennifer Lopez couldn’t have chosen a better time to launch or music career. The former “In Living Color” Fly Girl turned movie star arrived with her debut single “If You Had My Love” right as Latin pop was entertaining the mainstream. Lopez’s sound, helmed by producer Rodney Jerkins, was the most pop-friendly of the bunch. It also helps that she began a relationship with megastar mogul Sean “Puffy” Combs right around the time she was recording her debut album “On the 6.”
51. Barenaked Ladies - “One Week”
When: Oct. 17, 1998
Weeks on top: 1
Barenaked Ladies had some great alternative rock songs in the early 1990s. Then came “Chickity China, the Chinese chicken” and the miracle of a song that was “One Week.” The catchy song, which didn’t sound like anything else on the radio in 1998, went to No. 1. But it wasn’t the end of Barenaked Ladies, who continued to release successful alt-rock gems into the early 2000s and is still going strong today after crafting the theme song to “The Big Bang Theory.”
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50. Marky Mark & the Funky Bunch featuring Loleatta Holloway - “Good Vibrations”
When: Oct. 5, 1991
Weeks on top: 1
What has made “Good Vibrations” far more tolerable than the Nineties other poser-happy rap songs? The answer is simple: You’re not required to take it seriously. Whereas an artist like Vanilla Ice was begging for street cred, Marky Mark didn’t fit that part. It’s clear Mark Wahlberg was taking himself super serious as an emcee. But you couldn’t help but want to hug a guy who doubled as an underwear model and rolled with a crew called the Funky Bunch.
49. Mariah Carey - “Dreamlover”
When: Sept. 11, 1993
Weeks on top: 8
Lost among Mariah Carey’s other big hits (and there are many) was just how huge “Dreamlover” was. The song was used to launch “Music Box,” the follow up to “Emotions,” which received mixed reviews. But “Dreamlover” was universally loved and began a new style for Carey in the sampling of classic songs (in this case, the Emotions' “Blind Alley”), which would become a mainstay in her career.
48. Will Smith - “Gettin' Jiggy Wit It”
When: March 14, 1998
Weeks on top: 3
Of all Will Smith’s post-1980s rap songs, “Getting' Jiggy Wit It” is the easiest to love. For starters, it’s very catchy. But it also embodies the vibe Smith had cultivated in his movie career. “Getting' Jiggy Wit It” was nearly four-minutes of fun fit into the hip-hop good vibes of the time thanks to bouncy production from Trackmasters and L.E.S.
47. Janet Jackson - “Escapade”
When: March 3, 1990
Weeks on top: 3
Janet Jackson’s “Rhythm Nation” was such a huge album its hit singles kept going on into a new decade. Whereas most of Jackson’s music produced by Jimmy Jam and Terry Lewis were pioneering new jack swing, “Escapade” leaned more into dance-pop territory. Thus, it’s light-hearted vibe would serve as an inspiration to numerous pop divas moving forward.
46. Roxette - “Joyride”
When: May 11, 1991
Weeks on top: 1
Even more so than the group’s biggest hit, “It Must Have Been Love,” “Joyride” showed off Per Gessle’s ability to craft fantastic pop-rock songs. The song’s pop spirit and rock swagger mesh seamlessly. Its lyrical inspiration lied in the Beatles, as Gessle recalled an interview where Paul McCartney said writing songs with John Lennon was like “a long joyride.”
45. Coolio featuring L.V. - “Gangsta’s Paradise”
When: Sept. 9, 1995
Weeks on top: 3
Coolio’s “Gangsta’s Paradise” was an anomaly in 1995. It’s the only gangsta rap song to go to No. 1 that year. Of course, it had to be cleaned up a bit. Coolio, previously known for his upbeat party anthems, removed all swear words at the request of Stevie Wonder, whose hit “Pastime Paradise” provided the sample for the song.
44. Spice Girls - “Wannabe”
When: Feb. 22, 1997
Weeks on top: 4
If you look at what came before and after “Wannabe,” the song was a game-changer. Not only did it catapult the Spice Girls to global stardom. It changed the landscape of pop music, igniting a new and fruitful chapter in the genre’s history. MTV’s “Total Request Live” would debut within the next two years and the way girl and boy groups were marketed would forever change.
43. Aerosmith - “I Don’t Want to Miss a Thing”
When: Sept. 5, 1998
Weeks on top: 5
Aerosmith had been a band for nearly 30 years when it finally scored its first No. 1 hit. And it was with a song that none of the band members wrote. That honor goes to Nineties hitmaker extraordinaire Diane Warren, who crafted a slow-burner for the soundtrack to “Armageddon” driven by Steven Tyler’s otherworldly voice and an orchestral backing.
42. Ricky Martin - “Livin' la Vida Loca”
When: May 8, 1999
Weeks on top: 5
Songwriter/producer Desmond Child is a musical genius and served as the perfect fit for Ricky Martin to relaunch his career. Martin, previously known music-wise for his stint in the group Menudo, came out the gates strong with “Livin' La Vida Loca,” the hit from his debut English album. The song and Martin’s star took off, igniting the Latin pop craze of the late 1990s/early 2000s that saw Shakira, Marc Anthony, Enrique Iglesias and others become household names.
41. EMF- “Unbelievable”
When: July 27, 1991
Weeks on top: 1
For a single week in 1991, Andre Dice Clay sat atop the music world. Well, sort of. EMF’s fantastic alt-rock anthem “Unbelievable” has one heck of a groove and rhythm. But the thing that stood out most was the sample of the Dice Man shouting “Oh!” throughout the song. It’s a weird way to produce a hit, but it worked for the British band.
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40. Paula Abdul - “Rush Rush”
When: June 15, 1991
Weeks on top: 5
For all her dance-pop gems, it’s Paula Abdul’s weepy love song that stays with you most. “Rush Rush” was a big risk as Abdul’s first ballad. It was released as the lead single from her sophomore album “Spellbound.” But clearly, the sound suited her. Abdul’s scratch vocal, intended as a reference track, wound up sticking, as it contained the pain and vulnerability the demanded. Heck, even Keanu Reeves couldn’t resist playing her love interest in the popular music video.
39. Extreme - “More Than Words”
When: June 8, 1991
Weeks on top: 1
For those who don’t know, Extreme was a hard rock band (and an underappreciated one at that) who put together some stellar metal songs. Yet, when half the members grabbed acoustic guitars and put their hair up things went bonkers. “More Than Words” isn’t just a rock band doing an acoustic ballad. It’s completely stripped down and different from what Extreme was. Yet, great songwriting is great songwriting and the band was rewarded with a No. 1 hit.
38. New Kids on the Block - “Step By Step”
When: June 30, 1990
Weeks on top: 3
You might attribute New Kids on the Block to the 1980s. But the group released its biggest selling single in 1990. Looking back, “Step by Step,” which spent three weeks at No. 1, and its carefree dance-pop vibe became the blueprint for boy bands.
37. Wilson Phillips - “Hold On”
When: June 9, 1990
Weeks on top: 1
A decade or two ago, Wilson Phillips' inspirational anthem “Hold On” wasn’t regarded as anything more than a cheesy (maybe the cheesiest) pop song from the Nineties. But opinions change. For a generation big on nostalgia, it gets no bigger than “Hold On,” a song that has good times written all over it. Some people may still be willing to turn around and say goodbye. But there are thousands of bachelorette parties each year that are willing to fight for it.
36. Mariah Carey - “Emotions”
When: Oct. 12, 1991
Weeks on top: 3
It may have been the title track and lead single from Mariah Carey’s second album, but “Emotions” was a surprise from the singer. Joining forces with Robert Clivilles and David Cole of C+C Music Factory, Carey put her stunning voice over a dance tune that’s one step removed from disco. Listeners ate it up, giving Carey her fifth straight No. 1 on the Billboard Hot 100 to start her career.
35. Madonna - “Justify My Love”
When: Jan. 5, 1991
Weeks on top: 2
At the start of the 1990s, Madonna was out to prove she could do no wrong, even when she was at her most experimental. Written by Lenny Kravitz and Ingrid Chavez, “Justify My Love” was a trip-hop song released as the lead single from Madonna’s 1990 greatest hits album “The Immaculate Collection.” Initially, that made it seemed like a throwaway. It was anything but. “Justify My Love” stands as one of her best and most erotic songs, which is saying something.
34. All-4-One - “I Swear”
When: May 21, 1994
Weeks on top: 11
While Babyface was crafting hit records for Boyz II Men, similar-minded group All-4-One went a different route for its monster hit. “I Swear” is a cover of a John Michael Montgomery’s hit that spent a month atop the country charts. But All-4-One’s version was next level. Producer David Foster gave it a pop-finish that catapulted it to the top of the pop charts for nearly three months.
33. Prince & The New Power Generation - “Cream”
When: Nov. 9, 1991
Weeks on top: 2
Prince’s last No. 1 hit isn’t the song from his “Diamonds and Pearls” album you’d expect to top the charts. The title track and “Get Off” appeared to have more potential. But “Cream” fully realizes the sultry funk odyssey Prince was going for on his 13th studio album.
32. C+C Music Factory featuring Freedom Williams - “Gonna Make You Sweat (Everybody Dance Now)”
When: Feb. 9, 1991
Weeks on top: 2
It might feel a bit corny now. But no act was at the center of the early Nineties dance boom like C+C Music Factory was. With a handful of hits, the group became one of the most successful dance acts of all time. Their biggest hit “Gonna Make You Sweat (Everybody Dance Now)” gets a boost from singer Martha Wash, who (trivia alert) was a member of the Weather Girls (“It’s Raining Men”).
31. Boyz II Men - “I’ll Make Love to You”
When: Aug. 27, 1994
Weeks on top: 14
“I’ll Make Love to You” was so overplayed, you might roll your eyes at the sound of it today. But back in 1994, nothing was bigger. Boyz II Men’s hit, written by Babyface, spent 14 weeks at No. 1, tying the record (at the time) for the most weeks atop the Billboard Hot 100.
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30. Santana featuring Rob Thomas - “Smooth”
When: Oct. 23, 1999
Weeks on top: 12
The final No. 1 song of the 1990s on the Billboard Hot 100 was also No. 1 for two weeks into the 2000s. That’s how big Santana’s “Smooth” was. Interestingly enough, the song’s co-writer Rob Thomas had George Michael in mind as the singer of “Smooth.” But Santana wanted Thomas after hearing the demo version. As amazing as it would have been to have Michael on such a legendary track, it’s hard to imagine anyone by Thomas singing this hit, which Billboard ranked as the biggest overall song of the entire 1990s and the second most successful song in Billboard history.
29. Janet Jackson - “Love Will Never Do (Without You)”
When: Jan. 19, 1991
Weeks on top: 1
Janet Jackson’s “Love Will Never Do” rates as one of the best songs of the 1980s, appearing on her masterful 1989 album “Rhythm Nation 1814.” But the track didn’t go to No. 1 until two years after the album’s release. The reason? The majestic music video directed by Herb Ritts and featuring cameos from model/actors Antonio Sabato Jr. and Djimon Hounsou. The clip arrived in late 1990 and consumed MTV, propelling “Love Will Never Do” to the top of the charts at the start of the following year.
28. Céline Dion - “My Heart Will Go On”
When: Feb. 28, 1998
Weeks on top: 2
It’s the perfect combination of movie and music magic. “Titanic” arrived in late 1997 as the biggest film of all time. “My Heart Will Go On” serves as its main theme, written by James Horner and Will Jennings, and sang perfectly by Celine Dion. Those slight crackles in Dion’s voice are all you need to hear before the song takes off soaring. It milks the love story of “Titanic” for all its worth.
27. P.M. Dawn - “Set Adrift on Memory Bliss”
When: Nov. 30, 1991
Weeks on top: 1
One of the most unlikely No. 1 hits on this list and maybe the most complex. P.M. Dawn was a hot commodity in the conscious rap circles of the early 1990s but was gone pretty fast. Still, during their run, they delivered “Set Adrift on Memory Bliss,” a song built around a collection of odd samples that included Spandau Ballet’s “True,” The Soul Searchers' “Ashley’s Roachclip” and Bob James cover of “Tame Me to Mardi Gras.” Somehow it all amounts to four minutes of hip hop, well, bliss.
26. Lisa Loeb & Nine Stories - “Stay (I Missed You)”
When: Aug. 6, 1994
Weeks on top: 3
Lisa Loeb’s song “Stay” is the stuff of movies, both literally and figuratively. The song broke through after being featured on the soundtrack to the film “Reality Bites.” Loeb was friends with star Ethan Hawke. The track went to No. 1. The crazy thing was Loeb didn’t have a record deal yet, marking the first time that’d ever happened. Don’t worry, Loeb quickyyl earned a record deal and is still an active artist today.
25. Cher - “Believe”
When: March 13, 1999
Weeks on top: 4
If Madonna’s “Ray of Light” ushered in the idea of dance music moving beyond the clubs on into mainstream radio heading into the 21st century, then Cher’s empowering “Believe” cemented it. The only weird thing about the song is that Cher is the one singing it. She wasn’t exactly a teen-pop star at the time. But that doesn’t take away from its impact. You can still hear the influence of “Believe” in the mainstream today.
24. Sir Mix-A-Lot - “Baby Got Back”
When: July 4, 1992
Weeks on top: 5
“Baby Got Back” is the novelty song that never went away. You could put this on at a wedding today and women will recite the opening word for word before the rap breaks in and everyone (and I mean everyone) joins in. Sir Mix-a-Lot was never shy about playing up the songs “playful” nature, rapping on top of a giant butt in the video.
23. Mariah Carey - “Always Be My Baby”
When: May 4, 1996
Weeks on top: 2
“Always Be My Baby” might be the one Mariah Carey single where she’s more impressive as a songwriter (along with Jermaine Dupri and Manuel Seal) than a singer. The song isn’t set up to show off her amazing range. Instead, it’s one of the few Mariah songs you could imagine another singer having a hit with. That’s a compliment to its structure. Separate, the acoustic guitar, drum and piano parts on “Always Be My Baby” are all amazing. Meshed together, they’re pure magic.
22. Hanson - “MMMBop”
When: May 24, 1997
Weeks on top: 3
In the middle of 1997 driven by hip hop and R&B songs, there was Hanson. The running joke about the young brothers' hit was that you couldn’t make out most of the words. But that’s also a sign of its brilliance. It’s all about melody and the Hanson brothers were writing a top-level melody in the tradition of the greatest pop-rock songs of all time.
21. Blackstreet featuring Dr. Dre - “No Diggity”
When: Nov. 9, 1996
Weeks on top: 4
There’s no way “No Diggity” was going to be bad. It has two of the best producers and songwriters of their era on one track in Blackstreet leader Teddy Riley and Dr. Dre. The former even mimics Dre’s style with the song’s infectious piano-driven beat.
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20. Christina Aguilera - “Genie in a Bottle”
When: July 31, 1999
Weeks on top: 5
If Britney Spears' “Baby One More Time” established the blueprint for the new teen songstress heading into the new millennium, Christina Aguilera’s "Genie in a Bottle' blew it up a bit. Those opening runs shouldn’t be there. It defied the way the record labels pigeon-holed their young singers (just ask Robyn). But “Genie in a Bottle” was the perfect mix of anything. Aguilera didn’t need any Auto-Tune, but she also had no problem taking hold of a dance-pop track. She had it all.
19. Toni Braxton - “Un-Break My Heart”
When: Dec. 7, 1996
Weeks on top: 11
The writer-producer team of Diane Warren and David Foster weren’t about to slow play the drama on “Un-Break My Heart.” Right from the start, you can sense the heartache and the pain (as if the title wasn’t enough). Structure-wise, it’s a perfectly crafted pop song and Toni Braxton showcases the kind of restraint required to establish its appeal.
18. TLC - “Creep”
When: Jan. 28, 1995
Weeks on top: 4
Songwriter and producer Dallas Austin dug into his bag of tricks for TLC’s “Creep,” combining elements of soul, funk, jazz and hip hop along for a song builds on the sensual sound Prince delivered in the late 1980s and early 1990s. As always, TLC delivers the goods, especially T-Boz whose lead vocal matches the groove as if it was born to do so.
17. 2Pac featuring K-Ci & JoJo / Dr. Dre and Roger Troutman - “How Do U Want It” / “California Love”
When: July 13, 1996
Weeks on top: 2
The double A-side single is a lost art. Back in 1996, it was a smart move by Death Row Records to drop two songs together that showed both sides of 2Pac’s hitmaking capabilities. “California Luv” was the up-tempo anthem produced by Dr. Dre that came with the blockbuster video and vocals from Roger Troutman. “How Do U Want It” brought in K-Ci & JoJo of Jodeci to sing the hook on his song for the ladies.
16. Mariah Carey - “Vision of Love”
When: Aug. 4, 1990
Weeks on top: 4
“Vision of Love” was not the work of a seasoned veteran. It was Mariah Carey’s debut single. Let that sink in for a moment. The world had great singers. But this was another level. The rollout of Carey’s career at Columbia Records is the stuff of legend with every song and promotional push fine-tuned. That all beings with “Vision of Love,” a perfect slice of pop and R&B crafted by Carey and co-writer Ben Margulies that builds to its closing vocal gymnastics display.
15. The Notorious B.I.G. - “Hypnotize”
When: May 3, 1997
Weeks on top: 3
“Sicker than your average…” The opening lines to Biggie’s first No. 1 hit summed him up perfectly. Only he wasn’t around the witness the song’s success. Christopher Wallace was murdered on March 9 in Los Angeles, a homicide that remains unsolved. His masterful double album “Life After Death” would arrive a few weeks later. Fortunately, Biggie was around to record the video to “Hypnotize.” The clip, which became popular on MTV and helped keep his legacy alive moving forward.
14. Janet Jackson - “That’s The Way Love Goes”
When: May 15, 1993
Weeks on top: 8
This is the sound of sex on record. Everything from the opening whispers of a “moth to a flame” to that sensual bassline, “That’s The Way Love Goes” made Janet Jackson a sexual icon and ruled the charts for 8 weeks during the summer of 1993.
13. Boyz II Men - “End of the Road”
When: Aug. 15, 1992
Weeks on top: 13
When Michael Bivens of New Edition discovered Boyz II Men, he and Motown Records put the group under the vision of Dallas Austin for their debut “Cooleyhighharmony.” The results were fantastic. But it wasn’t until Boyz II Men joined forces with Babyface and L.A. Reid for “End of the Road,” featured on the “Boomerang” soundtrack, that the group became megastars. Babyface was at his hit-making peak and this was, arguably, his greatest moment. “End of the Road” spent 13 weeks at the top of the Billboard Hot 100, which was the record at the time.
12. Bone Thugs-N-Harmony - “Tha Crossroads”
When: May 18, 1996
Weeks on top: 8
It’s ironic that Bone Thugs-N-Harmony, a group caught up in politicians' criticism of gangsta rap during the first half of the 1990s would go on to release the most melodic and one of the biggest hip-hop songs of the decade. “Tha Crossroads” has its origin on Bone Thugs' debut sophomore album “E. 1999 Eternal” as a track called “Crossroad” dedicated to the group’s late friend Wally Laird III. However, the death of Eazy-E led to a remake and Bone Thugs' going to the top of the charts for two weeks.
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11. TLC - “No Scrubs”
When: April 10, 1999
Weeks on top: 4
“No Scrubs” is the blueprint for all the pop-driven, female R&B music that arrived (usually to chart-topping results) in the late 1990s and early 2000s. Fittingly enough, TLC’s hit was written by two women who helped shape the soulful girl-group boom of the Nineties in Kandi Burruss and Tameka “Tiny” Cottle of Xscape. The song and its futuristic video would also serve as a comeback for TLC, who had to declare bankruptcy after the release of their hugely successful “CrazySexyCool” and went on a hiatus.
10. Michael Jackson – “Black or White”
When: Dec. 7, 1991
Weeks on top: 7
To think in a decade when Nirvana exploded, R.E.M. went mainstream and Metallica dropped “The Black Album,” that Michael Jackson was responsible for the biggest rock sone of the 1990s from a charting standpoint. By all accounts, Jackson’s album “Dangerous” would never be as big as “Thriller” or “Bad.” But he was still the “King of Pop." That made everything Jackson did event viewing. In some sense, “Black or White” feels corny. Its video features Macaulay Culkin and a throwaway rap verse by the song’s producer/engineer. But that guitar riff is as good as anything this side of “Beat It” with Jackson morphing his voice into a gritty rock instrument while waxing poetic about racial harmony.
9. Brandy & Monica - “The Boy Is Mine”
When: June 6, 1998
Weeks on top: 13
You have to give Brandy credit. For as big of a pop star as she was in the 1990s, she wasn’t selfish. After recording a solo version of “The Boy Is Mine” with producer Rodney Jerkins, the duo drew inspiration from Michael Jackson and Paul McCartney’s 1982 hit “The Girl Is Mine” and decided to switch things to a duet. It was Brandy who chose Monica, setting in motion a music event that would rule the top of the Billboard Hot 100 for 13 weeks. Rumors of a feud between Brandy and Monica only made the song and its corresponding video even more popular.
8. Mariah Carey - “Fantasy”
When: Sept. 30, 1995
Weeks on top: 8
Before “Fantasy,” Mariah Carey was an adult contemporary star…a REALLY popular one. But with the arrival of her “Daydream” album, Carey and her team looked to expand her sound. Enter “Fantasy,” a dance-pop song built around a sample of Tom Tom Club’s “Genius of Love.” If the original version of “Fantasy" wasn’t enough of a game-changer for Carey, Sean “Puffy” Combs through Ol' Dirty Bastard on the remix. The rest as they say is history.
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7. Whitney Houston - “I Will Always Love You”
When: Nov. 28, 1992
Weeks on top: 14
Listening to the power of Whitney Houston’s “I Will Always Love You,” it’s hard to fathom it ever got dethroned from the No. 1 spot. It is the vocal performance to end all vocal performances, towering over the movie it was recorded for – “The Bodyguard” – and helping it become the huge success it was at the box office. And to think Houston’s cover of Dolly Parton’s classic almost didn’t happen. Houston was to record a cover of Jimmy Ruffin’s “What Becomes of the Brokenhearted” as the soundtrack’s first single. It was Kevin Costner who suggested “I Will Always Love You” with Houston and her team singing it in the style of Linda Ronstadt’s 1975 cover version, taking it to new heights.
6. Madonna - “Vogue”
When: May 19, 1990
Weeks on top: 3
“What are you looking at?” That’s how Madonna’s “Vogue” begins. But we all knew the answer. The start of the 1990s had us all looking at Madonna. And if you weren’t looking at her, you certainly were after “Vogue” and its iconic music video hit MTV. The song and its rollout are, arguably, the greatest example of Madonna’s genius. Working with Shep Pettibone, who had produced Madonna’s best dance songs up until that point, Madonna conceived the concept of the song (centered on a 1980s house dancing style) surely knowing the era she was in. The video, which featured Madonna and her dancers voguing, would explode and cement Madonna as an icon in a new decade.
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5. The Notorious B.I.G. featuring Puff Daddy & Mase - “Mo Money Mo Problems”
When: Aug. 30, 1997
Weeks on top: 2
You could argue no producer ever put together a greater five-week stretch than Sean “Puffy” Combs did during the summer of 1997. From the start of May through the end of September, songs produced by Puff ruled the Billboard Hot 100 for a total of 19 weeks interrupted only by Hanson for three weeks. The centerpiece of that run is The Notorious B.I.G.'s classic “Mo Money Mo Problems” feature Puff Daddy and Mase. The Diana Ross sample is pure genius, only taking a backseat to Biggie’s iconic closing verse.
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4. Britney Spears - “...Baby One More Time”
When: Jan. 30, 1999
Weeks on top: 2
The Nineties had several important a-star-is-born moments. But thanks to the rise of MTV’s “Total Request Live,” the debut of Britney Spears was the biggest. It wasn’t just that “Baby One More Time” was a perfect pop song for the times (written by Max Martin). It’s the amazing video as well with many of the key moves driven by Spears. From switching to the schoolgirl outfit right before filming began to deciding to tie up her shirt. Oh, and the entire getup was purchased at Kmart. It doesn’t get more Nineties than that.
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3. Lauryn Hill - “Doo Wop (That Thing)”
When: Nov. 14, 1998
Weeks on top: 2
“Doo Wop (That Thing)” doesn’t feel like it came out in the Nineties. Merging elements of rap, soul and doo-wop, Lauryn Hill’s solo classic sounds instantly timeless with its opening piano melody. Hill is a brilliant singer, while also ranking as one of the greatest emcees of all time (“Don’t be a hard rock when you are a gem”). No wonder Drake (and numerous others) have sampled it and other songs from the woman known as L Boogie.
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2. TLC - “Waterfalls”
When: July 8, 1995
Weeks on top: 7
TLC’s sophomore album “CrazySexyCool” had already produced two hits (“Creep” and “Red Light Special”). But when “Waterfalls” rolled around, it was a game-changer. Much of that is owed to the iconic music video that features liquified versions of members T-Boz, Left Eye and Chilli. But the video’s main purpose was amplifying the song’s message. Produced by Organized Noize and Marqueze Etheridge, “Waterfalls” flips some old Paul McCartney lyrics into a funky R&B song about drugs and violence and AIDS, with Left Eye’s most iconic rap verse as the cherry on top.
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1. Sinéad O’Connor - “Nothing Compares 2 U”
When: April 21, 1990
Weeks on top: 4
The legacy of “Nothing Compares 2 U” is interesting. Within the context of the 1990s, it is an ultimate power ballad, Sinead O’Connor’s crowning achievement and one of the simplest and most compelling music videos of all time. That alone could place it at the top of the list. But since the passing of Prince, more attention has been placed on the song he wrote. Prince’s version is funkier and more sensual. O’Connor’s is utterly heartbreaking. But with both, there is no arguing “Nothing Compares 2 U” is one of the greatest love songs ever written.