A loving glance under beautifully thick eyelashes here, a dash of murderous tendencies there, and a whole lot of that undisguisable raspy Long Island accent everywhere, these are just some of the components that make up a classic Chris Messina performance. Looking through the credits of Messina’s nearly three-decade career, he has an actor’s filmography equivalent best described by the phrase: “always the bridesmaid, never the bride.” And in another multiverse, Messina would already be the go-to Hollywood leading man (and Italian short king) we deserve. 

Throughout his varied career, he’s played a depressed househusband, a face-slicing maniac, an elementary school science teacher, a douchey boyfriend, a Nietzsche-worshiping murderer, an anti-Nazi comrade, and a wise-cracking OB/GYN. It’s clear no Hollywood casting agent should put Messina in a box. He’s a deeply underrated and sympathetic actor that brings his best into all of his movies, even if they aren’t the best. In honor of the actor’s 49th birthday along with his upcoming activist film Call Jane and the biographical musical film Dreamin’ Wild premiering at the Venice Film Festival this year, now’s a great time to look back at some of Messina’s standout performances amongst his impressive filmography. 

15. FAIRHAVEN (2012)

Where to watch: Tubi and Prime Video

Fairhaven, directed and co-written by Tom O’Brien and starring Chris Messina (who also serves as the other co-writer in his screenplay debut), is quite a mixed bag. It’s a tad uneven, and maybe a little too short for its own good. But, the reason I think it deserves placement on this list is because of Messina’s ability to showcase the sensitive underbelly of an abrasive and broken character. Messina plays a man named Dave who has essentially been estranged for over a decade from his small seaside community of Fairhaven, Massachusetts. When he is compelled to return home after his father passes, he has to confront all the people and the unresolved problems that made him leave in the first place. 

14. DEVIL (2010) 

Where to watch: Rentable on most platforms 

Sure, the M. Night Shyamalan-produced horror film didn’t open up to rave reviews, but you best believe that doesn’t mean Messina phoned in his performance. In fact, the reason this made the cut is because Devil marks his first foray into the horror genre, well that, and we just love a man in uniform. In the film, Messina plays a nihilistic cop overcoming alcoholism induced by the death of his wife and child a few years before the start of the movie. Messina slips into a more serious role here. He’s shouting, he’s distressed and his wide eyes and dark, full lashes are flared so wide at certain points that you can’t help but say to yourself, “damn, he’s seen some shit.” So, for those looking for his comedic chops, you won’t find them here, but I can’t wait to see what skills Messina brings to the Stephen King adaptation of The Boogeyman in 2023.

13. MONOGAMY (2010) 

Where to watch: Tubi 

Messina’s natural vibe as a laidback everyman is on full display in this indie film directed by Dana Adam Shapiro. In Monogamy, Theo (Messina) is anything but monotonous. He’s a wedding photographer by day, an amateur sleuth by night, but most importantly he’s a doting boyfriend/fiancé to his singer-songwriter girlfriend/fiancé Nat (Rashida Jones)…that is until he starts to become obsessed with the scandalous sex life of one of his clients. The chemistry between Messina and Jones is both palpable and lived in. Both actors indulge in heartbreaking subtly to portray the very real struggle of a couple falling in and out of love. A particular highlight of this film is the post-breakup scene that involves Messina and Jones going to a dark place after the disillusion of the relationship, Messina’s broken soft cries are hard to watch up close. 

12. THE SWEET LIFE (2016) 

Where to watch: Hulu, Tubi, Roku, and YouTube

Though the movie doesn’t really find what it’s trying to say until the third act, Messina’s performance as a listless adult going on a suicidal road trip is a class act. The Sweet Life is a dark comedy that follows the story of an ice cream salesman named Kenny (Messina) whose mundane life is upended after running into a troubled woman who goes by the moniker of Lolita. To be honest, the film’s subject matter and jokes are a bit outdated, but it’s meant to be more of a PSA on accepting the struggles of life, contemplating your existence, and finding something to live for. Aside from the plot, it’s a good character study in Messina’s range, if nothing else. He plays the role of a lifeless man with deadpan humor and great sensitivity. The highlight of the film here is a moment where Kenny threatens to shoot a misogynistic man after harassing Lolita, it’s not very often that we see an angry Messina. 

11. ALEX OF VENICE (2014) 

Where to watch: Crackle and Vudu

Alex of Venice not only marks Messina’s directorial debut but the film also showcases the beautiful way he lets the camera linger in contemplative silence. Alex of Venice written by Jessica Goldberg, Katie Nehra, and Justin Shilton stars Mary Elizabeth Winstead and Chris Messina as high school sweethearts on the precipice of divorce. The plot centers on Alex (Winstead), a hardworking environmental lawyer weighed down by her quirky young son and her dementia-addled father (Don Johnson). Due to her busy schedule, her artist husband George (Messina), who bares the brunt of taking care of them in addition to housework, grows tired of the uneven path their relationship has taken and decides to call their marriage quits. To be fair, he doesn’t get a lot of screentime in this film, but when he does it’s heartfelt, moody, and peak Messina broody. The film’s placement on this list has to do more with his camerawork than his and Winstead’s vulnerable acting. 

10. I CARE A LOT (2020)

Where to watch: Netflix

This entry is sort of cheating. Messina only has two scenes in the Netflix crime dark comedy I Care A Lot. But those two scenes are the most charismatic of the bunch. In the film, Messina plays a smarmy charismatic mafia lawyer that tries to stop Rosamund Pike’s character from conning old women out of their money while in hospice. I can’t help but wonder if he was cut out of the film in later scenes, but either way, it was nice seeing Messina be a charismatic douchebag, he doesn’t do it enough. 

9. IRA & ABBY (2006)

Where to watch: Rentable on most platforms

This film marks his first leading role in a romantic comedy and what a chaotic role it is. Written by actress and co-star Jennifer Westfeldt, Ira & Abby is like a twisted take on When Harry met Sally. Messina plays Ira, a neurotically pessimistic therapist in training who thinks he has everything and nothing figured out. He suffers from indecisiveness, he’s self-deprecating, and never sees a task all the way through. (There’s even a line in the movie where he admits he never likes to keep anything in his apartment that dies, like dogs and fresh produce.) Ira’s meticulous lifestyle is thwarted when he meets the bubbly and aloof Abby (Westfeldt) who suggests that they get married after just one day of knowing each other. She’s quirky, he puts up with it, she tries to mellow him out, he tries to make her conform to societal standards, you know how it goes. Messina definitely channels a Billy Crystal vibe in his constant pivot from being endearing, annoyed, and tickled by his new bride. Forget the Kardashians, it’s keeping up with Messina’s bevy of emotions that makes this a good watch. 

8. LIVE BY NIGHT (2016) 

Where to watch: Rentable on most platforms 

Full disclosure: we have Ben Affleck to blame for Messina’s reduced role in the last couple of seasons of The Mindy Project, and honestly, I don’t know if I will ever forgive both of them for co-conspiring like this, I mean honestly, can you imagine how Danny and Mindy would have flourished if not for that Season 4 separation? (I’m looking at you too, Argo!) But, alas, I must digress. Since Messina had to leave for something, at least it was this. Not critically loved, but Live by Night next to Messina’s role in Birds of Prey is a pretty fun time — for his character at least. In the film, a meatier Messina takes on the role of Dion Bartolo, a crudely funny and intensely loyal mafia honcho who is only second in command to Joe Coughlin (Affleck). If you loved his gun-toting in Birds of Prey, you’ll certainly love his wit and sass here. 

7. THE SECRETS WE KEEP (2020)

Where to watch: Hulu

In this post-World War II thriller, Messina plays the ultimate “wife guy” to Scandinavian juggernaut Noomi Rapace. Messina has played the husband or boyfriend of many an actress, but none are more about the married life than this guy right here. It’s best you know little about this film before watching, but essentially Messina plays an army doctor who is forced to commit various crimes when a mysterious man from his wife’s past comes into the picture. While Messina takes a backseat to the powerhouse acting done by Rapace, he does manage to pack one hell of a devastating emotional punch in the last few scenes of the film that still haunts me to this day. 

6. 28 HOTEL ROOMS (2012)

Where to watch: Tubi

If his character in The Secrets We Keep is the ultimate “wife guy”, then his role in the indie romantic drama 28 Hotel Rooms is the perpetual “girlfriend guy.” Directed by Matt Ross — who would go on to also direct Messina in Starz’s Gaslit — 28 Hotel Rooms follows the story of two characters simply named Man (Messina) and Woman (Marin Ireland) over the course of 10 years while they carry out their torrid affair in, you guessed it, 28 different hotel rooms. In the beginning, their affair was simple, Man, a chatty celebrity book author was enamored by Woman, an introverted financial risk analyst, it’s a classic story about opposites attract. But as the days, months, and years go on their happy hook-ups turn into something deeper, something much more sorrowful. As the film progresses, it becomes a decent case study for monogamy and other moral gray areas in relationships. While the tone of the film is a bit uneven and aimless at times, Messina carries the emotional throughline of the film of a heartbroken man. A highlight of this film is Messina’s rage that comes in the third act of the film, I don’t know if he’s really had a chance to truly showcase unbridled rage, but man is it scary and compelling to see him in action. I would hate to be on his bad side. (P.S. — similar to his later role in Sharp Objects you get a lot of full frontal here, not that I’m complaining. It’s clear Messina is not afraid to bare all his vulnerabilities on the world stage.)

5. SHARP OBJECTS (2018)

Where to watch: HBO

In Jean-Marc Vallée’s Sharp Objects, Messina plays a dangerously sexy role as the hardboiled detective that gets a little too close to the nosy reporter impeding the investigation of a murder. Other than giving us full frontal, Messina maintains the head of his class when it comes to playing complicated handsome jerks who do the right things for the wrong reasons. It’s so fun to see him banter back and forth with Amy Adams as he tries to demystify her. Their relationship is much more complicated here than it ever was in Julie & Julia. 

4. THE SINNER Season 3 (2020)

Where to watch: Netflix 

If you thought his role in Birds of Prey was intense, Messina was really on some freak sh*t in Season 3 of Netflix’s crime anthology The Sinner. He was jumping off of bridges for fun, stabbing people in restaurants, singing cryptically about prickly pears, obsessed with death, and possibly repressing a sexual experience with his former roommate and male best friend (Matt Bomer) since college. Like, goddamn. I don’t know what kind of skeletons Messina unearthed from his closet to play this wacko, but it was thrilling and terrifying to watch him do it. His chemistry with Bomer is palpable. So, I suggest you run along and watch this, yesterday. (Something to note here: you don’t have to watch the previous seasons to jump straight into this one. And shoutout to the actor who plays a young version of Messina in a couple of episodes, he nailed his mannerisms and accent. NAILED it.) 

3. BIRDS OF PREY (2020) 

Where to watch: HBO

Birds of Prey? More like, Weirdo of Slay. I mean seriously, is there a character more iconic than Victor Zsasz in Cathy Yan’s Birds of Prey? Messina could have simply been a dull and doting henchman with a weird penchant for slicing off faces. But instead, Messina answered the call of his loyal underground fanbase and ramped up the latent BDE (big dick energy) and SSGE (sexy short guy energy) that we always knew he possessed. Don’t get me wrong, Zsasz is a total nutjob, and I do not endorse his crimes. But I do absolutely endorse the sexual chemistry between him and Ewan McGregor and the way he is just a little chaotic freak. More of this, please. It’s certainly his most fun role to date. 

2. THE GIANT MECHANICAL MAN (2012)

Where to watch: Peacock, Tubi, Crackle, and Prime Video

The Giant Mechanical Man is a gentle romantic comedy that follows the story of two aimless adults who are semi-jaded by life and the monotony of a nine-to-five job. Messina plays Tim, a struggling street artist who longs to be valued for his natural talents without having to succumb to the pressures of standard adult living. Jenna Fischer plays Janice, an insecure adult who shuffles through meaningless jobs hoping that one of them will evoke passion or a higher purpose. After befriending each other while working at a local zoo, they help each other realize that it only takes one special person to make life worthwhile. In this movie, Messina gets to play an awkward, stumbly dude in the process of falling in love, which is something we don’t really get to see in his other roles because he usually starts off a film or series attached to someone. Next to Danny Castellano (in Seasons 2–3), I would say that The Giant Mechanical Man, should be considered one of his best rom-com roles to date. 

1. THE MINDY PROJECT (2012–2017) 

Where to watch: Hulu

First, we have to thank Mindy Kaling for casting Chris Messina on The Mindy Project. Yes, Messina had been in the game long before this show aired, as evidenced on this list, but it was this show that was the gateway drug for most people who entered the Messina Cinematic Universe. Messina’s role as the leather jacket-wearing, Rudy Giuliani-loving, exercise junkie, and quirky curmudgeon OB/GYN Danny Castellano is quite controversial. Yes, Danny has the tendency to be rude to everyone in the office, including Mindy. Yes, Danny isn’t the greatest at expressing his feelings. And yes, Danny is sometimes too Catholic for his own good. But damn it, on the seldom occasions Danny does show his love and affection for Mindy—before and after he becomes her boyfriend—he does it well. Who can forget the Aaliyah dance he did for her after she had a bad time at the Christmas party? Or how about when he realized he loved her during airplane turbulence because he thought he wasn’t going to get another chance to tell her? Even when their relationship starts to dissolve in an admittedly cruel and manipulative way in Season 4, where Messina’s role was significantly reduced until the series finale, Messina really manages to sell the audience on nice guy gone bad. Despite the show’s hiccups, Danny will forever be my school girl crush, and a great show to perfect showcase Messina’s first foray into comedy — seriously, each season you can tell he loosens up with the quips —, his seasoned emotional romantic beats, and his ability to tap into complex nuance.