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10 Years, 3 Directors, 1 Vision: Inside Writer Josh Singer’s Long Journey to Make ‘Maestro’

The Oscar-winning screenwriter thrives when he gets to write alongside his directors. As he tells IndieWire, the protracted road to getting there with Bradley Cooper was worth it.
LOS ANGELES, CALIFORNIA - DECEMBER 12: (L-R) Josh Singer and Bradley Cooper attend Netflix's Maestro LA special screening at Academy Museum of Motion Pictures on December 12, 2023 in Los Angeles, California. (Photo by Emma McIntyre/Getty Images for Netflix)
Josh Singer and Bradley Cooper attend Netflix's "Maestro" L.A. special screening at Academy Museum of Motion Pictures on December 12, 2023.
Getty Images for Netflix

Josh Singer takes a lot of notes. For an in-demand screenwriter like him (to wit: “Spotlight,” “The Post,” “First Man,” and those are just his best-known produced works) that makes sense, but Singer’s latest project, Bradley Cooper’s Leonard Bernstein biopic “Maestro,” required even more copious files and neat notes. After all, Singer has been working on it for over a decade.

Over a recent Zoom interview with IndieWire, Singer narrated a little bit of his typical notes-finding experience: “Hold on, let me go into files. I’m going into my Bernstein file, which is very long, and then I’m going into, OK, here: Essentially, in 2008 [producers] Fred Berner and Amy Durning approached the Bernstein family, and they wound up, over the next two years, negotiating life rights.”

This is just the start of the odyssey. By 2010, the producers started looking for a director. Sometime around 2013, they locked in Martin Scorsese to direct. Soon after, they came knocking at Singer’s door.

More notes from Singer: “The story of my odyssey with this project is told in playlists,” he said. “I have about a dozen playlists, which end with the playlist, now on Spotify, which I love, which is the actual album of the movie, which has all the recordings that are from the movie. But literally, I made a playlist for Marty for that very first pitch, which was in spring of 2013. I wanted to pitch him and do the music cues as I pitch. And he was like, ‘No, no, no, no, that’ll confuse me. I know them all anyway.’ Which he did.”

As Singer recalls it, the meeting with Scorsese and then-studio Paramount Pictures was great. “It was one of those like, ‘Oh, wow, I just met Marty Scorsese’ [meetings], and he loved the pitch,” the writer said. “They bought it in the room, but it took them two years to make the deal.”

But if you know anything about Singer’s career, two years would take us to 2015, when he was a little busy with the imminent release of Tom McCarthy’s “Spotlight,” which would eventually go on to win both Best Picture and Best Original Screenplay (an award he shared with McCarthy). And he was also working on Damien Chazelle’s “First Man,” which would be released in 2018. Long story short: He didn’t get started on “Maestro” until about 2016, three years into the process.

By the fall of 2017, Singer, Berner, and Durning were ready to share their script with Scorsese. “The script was very different [than the final version],” Singer said. “There’s almost nothing that is the same, a couple of lines, maybe. I only really focused on the ascent of Lenny, going from his debut to when he takes over the Philharmonic in ’57. I was terrified of what happened later in his life, I just was afraid to go there.”

Mostly, Singer said, his first script was about Bernstein’s professional concerns. “Is he going to be a musical theater composer or is he going to be a conductor of orchestras? Those sort of questions,” Singer said. He re-read that draft recently, he said, and while he still found it “clever,” he was struck by what was lurking underneath all of that, his initial B story, which was all about Bernstein’s relationship with his wife, Felicia Montealegre. 

“The B story was Felicia, that she was the one who provided the grounding that enabled him to flourish,” Singer said. “But it was very much just a happy story. The A story was much more a ‘Great Men of History’ thing. I was young, younger, and again, it was clever. I was trying to do a little bit of ‘8 1/2,’ like Fellini.” 

MAESTRO, Bradley Cooper as Leonard Bernstein (left), 2023. ph: Jason McDonald / © Netflix /Courtesy Everett Collection
“Maestro”©Netflix/Courtesy Everett Collection

By then, however, they’d lost Scorsese, who was out the door to direct “The Irishman” (as Singer recalled, “Marty read it and was like, ‘I love the project, but this isn’t for me to direct’”). Another director, however, was interested: Steven Spielberg, who came on board in 2018, one year after Singer helped him with a quick re-write on “The Post.” Singer said the pair worked on the script for about six months, during which Cooper heard about the project and expressed interest in starring in it.  

“We wound up sending the script to Bradley, who read it immediately, like he literally was vacationing in Fiji and yet he read it immediately, that same day. Steven and I were both staggered by how fast he read it,” Singer said. “Within 24 hours he was like, ‘I’m in, I have a lot of thoughts, but I’m in.’ And then for the next 24 hours, I had Steven directing Bradley from my script.”

As Singer recalls now, another 24 hours or so passed before Spielberg pulled the trigger (he may be taking a bit of creative license with this timeline): He couldn’t do “Maestro,” he wanted to do his “West Side Story,” which finally seemed to be coming together. Cooper, he said, was quick on the draw: He wanted to direct it. But he understood if anyone was feeling gunshy, and he asked Singer and Spielberg to watch his “A Star Is Born,” which he’d recently completed filming. 

Singer laughed, because he knows everyone has heard this story already, but it is a good one. “We all went to see ‘A Star Is Born,’ and we were all blown away,” Singer said. “You’ve heard this story: In the first 10 minutes, Steven leans over to Bradley and says, ‘You’re fucking directing “Maestro.”’ It was this amazing thing.” (Both Spielberg and Scorsese produced the film, along with Cooper, Berner, Durning, and Kristie Macosko Krieger; Singer is an executive producer on the project.)

Still, Singer is honest about feeling some stress over the situation, or at least over his seemingly dueling projects. “That experience was very mixed for me because, on the one hand, I was thrilled because Bradley Cooper’s a real director,” he said. “I watched that film, and I’m like, ‘Oh my God, he’s a real director and he wants to direct this movie and it’s fantastic that he wants to do that and star and now I’ve got one of the greatest stars on the planet as well as one of the greatest directors on the planet directing my movie.’ On the other hand, I’ve got ‘First Man’ coming out a week after ‘A Star Is Born’ and I’m really not happy about that. I think I called and left Damien a message and said, ‘I have good news and bad news. Sadly, the good news is just for me.’”

“First Man”

And while Singer was thrilled about Cooper’s involvement — he had such a strong vision that he almost immediately met with the Bernstein children, who loved his ideas — only a few weeks into the new partnership, he began to worry about his own place within the project. “I start hearing these words: ‘Page one rewrite,’ which, as a writer, you never want to hear,” Singer said. “I knew we were going to do some work. I knew he was really fascinated with when Lenny got older, but you don’t want to hear ‘page one rewrite.’ Often when you hear that, the next set of words is, ‘And I’m bringing in my own writer.’”

That’s not what happened. Singer said while Cooper was honest about wanting to, in many ways, “start from scratch,” the filmmaker and star was effusive about the great work Singer had already done — and wanting to continue that great work, together. They quickly got to work.

The pair pored over all sorts of material, particuarly John Gruen’s book “The Private Life of Leonard Bernstein,” which chronicled a summer in Italy with the family and offered both “fantastic, beautiful pictures of all the kids and Lenny and Felicia” and a series of “incredible, extensive interviews” of which they also had access to audio versions. “It was hard to keep up with him listening to all those interviews,” Singer said. “He was like, ‘This is fascinating. This marriage, this family is fascinating.’ Even though it is very specific — this is a queer man — it’s way ahead of its time. Lenny and Felicia’s pact was, in some ways, something that was done back then, but also something, the way they did it, was I think very modern.”

Cooper, Singer said, “was really struck by that and really struck by these people and how they related to each other. The way they talked was so hyper-intellectual and verbal, and yet at the same time was somewhat emotionally obtuse. They just were somewhat disconnected.” That’s what he wanted the pair to follow for their script. 

“It became clear, that’s our story, that marriage is our story,” Singer said. “Once we found that and started moving forward, it was incredible. I was stunned by how much Bradley was focused on the research, how deep he went. This was him rolling up his sleeves and, just like my partnership with Tommy [McCarthy], I’d write some scenes, he’d write some scenes, he’d rewrite my scenes, I’d make notes on his scenes. It was very much integrated in that fashion.”

Tom McCarthy and Josh Singer - Original Screenplay, Spotlight88th Annual Academy Awards, Press Room, Los Angeles, America - 28 Feb 2016
“Spotlight” writers Tom McCarthy and Josh Singer with their Best Original Screenplay Oscars in 2016David Fisher/REX/Shutterstock

This went on for years, in part because of the pandemic. “We were going to shoot this two years ago, and we couldn’t do it, because we wanted to shoot live orchestra, and you couldn’t do that during the pandemic,” Singer said. “We’d wind up putting the script down and coming back to it three months later. It’s the greatest thing for a script, because you can see what doesn’t work with more objective eyes. We just constantly were at it and at it and at it, doing dozens and dozens of drafts. What we came to was a story that is much more emotional and much more universal than anything I really had in my first draft.”

The experience with Cooper, that partnership, is part of Singer’s secret sauce as a screenwriter. He’s someone who doesn’t just welcome collaboration, but who does his best work in tandem with other creators. “The nice thing about being the screenwriter as opposed to the director, when you work with the director, you have your compass, your director is the true north,” Singer said. “I’m not so good at being my own true north, but I love to work hard and I love to go deep, and all I really want is someone who’s going to push me to work hard and go deep.”

The directors Singer has thrived with — McCarthy and Chazelle and Cooper and Spielberg — are all, as he sees it, “serious people who do the work and who know how much work it takes and how deep it takes to go.” That pushes Singer in ways he finds necessary. “The other thing you probably need to work with Tommy or Damien or Bradley or Steven is endurance,” he said. “You’ve got to be able to be flexible, because one of the wonderful things about all of them is they’re all very good at not only blazing a path, but then standing back, looking at that path and saying, ‘Maybe not. Let’s go this way. Let’s go that way.’ You’ve got to be able to turn with them.”

Maestro. (L to R) Carey Mulligan as Felicia Montealegre and Bradley Cooper as Leonard Bernstein (Director/Writer/Producer) in Maestro. Cr. Jason McDonald/Netflix © 2023.
Behind the scenes on “Maestro”Jason McDonald/Netflix

Often, Singer said, he and Cooper would read their script aloud to each other, something he’s never done with anyone else. “I found it incredibly useful, because it’s a way to get a little more objective when you hear the lines out loud,” he said. “He’s not acting, he’s just reading, as am I. I’m reading Felicia, he’s reading Lenny. I made a pretty good Felicia, I have to say, but I didn’t do an accent or anything, but I think I got the emotion of it. But we’re not really acting. We’re just reading the lines aloud and you hear them in this really great way.”

Those readings eventually found the space for another collaborator. “The first time he invited Carey [Mulligan] to join us, I was so nervous, I’m just like, ‘I hope I don’t fuck up the lines,’” Singer said. “I’m literally just staring at my script, trying to concentrate super-hard so I don’t screw anything up. But just listening to them, the chemistry was already apparent to me, and the way Bradley and Carey have different energies that sort of mirror Lenny and Felicia’s different energies.”

Even before they shot a second of film, Singer said, he felt it, he knew, and he could stop looking at his notes. “It was realizing, ‘Oh, we’ve done good work, but it’s just going to far surpass what’s on the page,’” Singer said. “And knowing how hard we worked and all the work we poured in and thinking like, ‘Oh, it was worth it.’”

“Maestro” is now streaming on Netflix.

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