The Great Directors — And the One Musical They Made

Steven Spielberg has made blockbusters, thrillers, war films, con-artist movies, moody sci-fi studies, a Holocaust drama and The Terminal. But as he’s about to turn 75, he’s trying something new: With his remake of West Side Story, he’s completed his first-ever musical. “I’ve always wanted to make a musical,” he said way back in 2004. “Not like Moulin Rouge, though — an old-fashioned, conservative musical where everyone talks to each other, then breaks into song, then talks some more. Like West Side Story or Singin’ in the Rain.” Seventeen years later, that dream has finally become a reality.

Musicals are such a unique genre, requiring a level of technical skill that goes beyond other types of movies. Choreography and musical numbers are part of the mix, and you have to find the right cast who can dance and sing as well as act. (In the old days, sometimes the stars would have more polished vocalists handle the singing for them.) Then there’s the complex tonal reality of a musical, which can sometimes combine fantasy with everyday life — not to mention the shocking strangeness of, out of nowhere, people suddenly starting to belt out everything they’re thinking.

Because of those challenges — and the genre’s connection to Hollywood’s golden era — you can understand why major filmmakers like Spielberg are tempted to do a musical at least once. With that in mind, I’ve put together a list of some world-class auteurs who made one — and only one — musical, rendering a verdict on how well each of them did. My big takeaway: These revered auteurs often dropped the ball, humbled by just how hard it is to make a great musical. 

Joseph L. Mankiewicz

The Musical: Guys and Dolls (1955)

The Backstory: The man behind A Letter to Three Wives and All About Eve was an accomplished writer-director known for his elegant, witty films. Mankiewicz, whose older brother Herman was the subject of last year’s Mank, signed on to adapt the 1950 Tony-winning Guys and Dolls, which featured suave gamblers and tough-talking broads. For the film, he cast Frank Sinatra (an incredible singer) and Marlon Brando (not an incredible singer), a decision that powerful producer Samuel Goldwyn supported, saying, “I wanted everything about this picture to be honest.” Rather than having a natural singer dub Brando’s voice, the filmmakers wanted the real thing, flaws and all.

How Did It Turn Out? The movie was a hit, and it remains beloved, although not to the level of other 1950s musicals such as Singin’ in the Rain. Still, Mankiewicz’s sophisticated comedic stylings shine through in his Guys and Dolls — even if some of the singing, specifically Brando’s, isn’t so hot. “It’s not so important to be able to sing well as perform the song,” Brando said during an interview on set. That’s true, but being able to sing does count for something.

Martin Scorsese

The Musical: New York, New York (1977)

The Backstory: Scorsese is a filmmaker who cares passionately about music — he’s directed a few concert films, and his needle drops in Mean Streets and Goodfellas are deservedly lauded — but it wasn’t until New York, New York that he crafted an all-out homage to old-school movie musicals. An ambitious melding of tones, the film starred frequent Scorsese collaborator Robert De Niro as a saxophonist who falls in love with singer Liza Minnelli, their professional and romantic lives interweaving. 

How Did It Turn Out? At a moment when Scorsese seemed to be ascendant — Taxi Driver had just come out the year before — New York, New York was a commercial and critical dud, with viewers thrown by its juxtaposition of bygone Hollywood glamour and a bittersweet romantic drama. However, the film’s reputation has improved over the years as new generations embrace its audacity and stunning design. 

Just don’t tell that to its director. “I’m not happy with it,” Scorsese said in Conversations With Scorsese. “But the thing about it is that I still think the idea of mixing a modern foreground with an artificial background, like the old Hollywood, was a good idea.”

Sidney Lumet

The Musical: The Wiz (1978)

The Backstory: The New York filmmaker was best known for his terse, character-driven dramas (12 Angry Men, Dog Day Afternoon) and the angry satire Network. But he also tried his hand at this adaptation of the Broadway musical, which told the story of The Wizard of Oz through Black characters. 

“My love of New York had a lot to do with it,” Lumet said in 2007 when explaining why he took a chance on directing The Wiz. “I had an idea which was that one of the best ways of doing a fantasy was to use reality. And I wanted to do a picture in which New York City itself became unreal.” You couldn’t argue with the talent assembled: The movie boasted new songs from Quincy Jones, a screenplay by former costume designer Joel Schumacher (who would go on to direct everything from The Lost Boys to Batman & Robin) and a cast that included Diana Ross, Michael Jackson, Nipsey Russell, Lena Horne and Richard Pryor.

How Did It Turn Out? The film tanked at the box office, although it’s viewed slightly more fondly today, especially in the Black community. In an essay commemorating The Wiz’s 40th anniversary, culture critic Gerrick Kennedy wrote, “For a generation of Black Americans, this was the first time they saw people who spoke, sung and moved the way they did. … [The film] weaved together gospel, blues, soul and R&B — genres that are unequivocally Black creations — and were narratives of the Black experience, an especially bold move given Hollywood’s monochromatic palette.” 

Still, Lumet lamented that his inexperience with musicals sabotaged the project. “I didn’t know enough technically,” he told DGA Quarterly, later adding, “[M]ore and more of the shooting got relegated to the studio. So I was losing the whole point of why I wanted to make it in the first place. Because I couldn’t tell them how it could be done. So it was just sheer chutzpah on my part to bite that off at that time.”

Francis Ford Coppola

The Musical: One From the Heart (1982)

The Backstory: Few directors had a more sterling run in the 1970s than Coppola, who delivered two Best Picture-winning Godfather pictures, The Conversation and Apocalypse Now. His first film of the 1980s was no less ambitious, a hyper-stylized, imaginatively designed musical about a discontented couple (Frederic Forrest, Teri Garr) who go off looking for their ideal romantic partners. 

“After spending 16 months in the jungle, I thought there had to be another way to make movies,” Coppola said. “Apocalypse Now was such a grueling shoot that I wanted something completely different, so One From the Heart was really the antidote to Apocalypse. … I wanted to go in a new direction where I could really control the elements of the shoot, without having to deal with concerns of weather, sunlight and historical accuracy.”

How Did It Turn Out? Heaven’s Gate is often cited as the moment that the New Hollywood era ended — here you had a visionary director in Michael Cimino who delivered an expensive boondoggle that neither critics nor audiences cared for. But One From the Heart, which came out a few years later, could also be ground zero for that industry shift, severely harming Coppola’s reputation. 

“I was very depressed at the time [after One From the Heart], which was a heartbreak to me and involved some stupidity on my part,” Coppola admitted recently. “And I was very despondent about the terrible reaction.” That said, the movie has subsequently earned a cult following because of the clear passion he brought to the endeavor, and the Tom Waits songs (featuring vocals from Crystal Gayle) remain pretty damn lovely.

John Huston

The Musical: Annie (1982)

The Backstory: By the early 1980s, the veteran writer and director had already amassed a hall-of-fame career, including two Oscars and a body of work that included classics such as The Maltese Falcon, The Treasure of the Sierra Madre, The African Queen and The Man Who Would Be King. (Funny enough, he also directed a Moulin Rouge decades before the Baz Luhrmann film, except Huston’s wasn’t a musical.) Annie had been a hit on Broadway when it premiered in the late 1970s, and although he’d never done a musical before, Huston cast sure-shot performers like Albert Finney, Carol Burnett, Bernadette Peters, Tim Curry and Ann Reinking — alongside newcomer Aileen Quinn as Annie — for the big-screen version. 

“John was very good about letting us go with it,” Burnett later said. “He believed that you hire a person because of what they can bring to the movie, so you don’t try to tell them how to do it. Annie was shot very quickly. I don’t think we did more than two takes for a scene. He knew what he wanted and would say, ‘Okay, we’ll move on now.’”

How Did It Turn Out? Critics killed Annie, with the film generally regarded as one of Huston’s worst. It didn’t help that the movie was expensive for its time, costing perhaps as much as $50 million. “I remember turning to Bernadette and saying, ‘This may well be the last big movie musical,’” Curry said last year. “That was a distinct possibility, and, pretty much, it was. Hollywood rarely makes a musical of this kind, and on this scale these days, and that’s a shame. At the time, there was a lot of criticism about how much the movie cost. It would be a drop in the ocean these days.”

Woody Allen

The Musical: Everyone Say I Love You (1996)

The Backstory: In the mid-1990s, Allen was on a roll. His previous two pictures, Bullets Over Broadway and Mighty Aphrodite, had been both Oscar-winners, and his working relationship with powerhouse arthouse distributor Miramax gave him total creative freedom. And so he decided to make a musical, casting stars like Drew Barrymore, Goldie Hawn, Edward Norton, Natalie Portman and Julia Roberts to tell the story of several members of a New York family as they grapple with matters of the heart. Allen didn’t care if his actors were talented vocalists, wanting the singing to be comparable to how people are in real life. 

“There are times when you’re in the shower or your car or at a party and you just sing because you feel good or rhythmical or exuberant or sad,” he said at the time, later adding, “It’s an expression of emotion, and I wanted the actor or actress to act the scene and then, when it came to a certain point, sing the thing rather than just go on with the dialogue.”

How Did It Turn Out? In that same interview, Allen admitted his original cut was more than three hours long — the final film is only about 100 minutes — which required him to excise entire subplots involving, among others, Liv Tyler. Not surprisingly, then, Everyone Says I Love You feels truncated and a bit scattered — a likable but pretty minor Allen film that features some awkward (albeit occasionally charmingly awkward) singing and dancing. Put it this way: Even the director’s “separate the art from the artist” defenders tend not to go to bat for this film over, say, Annie Hall. 

Lars von Trier

The Musical: Dancer in the Dark (2000)

The Backstory: Thanks to the acclaimed, audacious Breaking the Waves, a searing drama about a woman who’s convinced that God talks to her, Danish filmmaker von Trier was a critics’ darling, celebrated for his provocative, even combative films. He rolled the dice again for this anti-musical musical, which starred Björk as a kindly immigrant working a backbreaking job who’s happiest in her mind, where her life occasionally features song-and-dance numbers. But the director eschewed the polish we’re used to seeing in musicals, preferring a grubbier look and a more slapdash approach to the choreography, which intentionally made the sequences feel more mundane than the typical Hollywood fantasia. “Maybe it doesn’t look like a conventional musical,” von Trier said, “but it’s a musical to me,” 

How Did It Turn Out? Dancer in the Dark won the prestigious Palme d’Or at that year’s Cannes Film Festival, and one of Björk’s songs from the movie, “I’ve Seen It All,” landed an Oscar nomination. (The infamous “swan dress”? That happened during that Academy Awards.) The film was an arthouse sensation, but in recent years its reputation has been diminished because of Björk’s claims that von Trier sexually harrased her during production. (Among her accusations: “While filming in Sweden, he threatened to climb from his room’s balcony over to mine in the middle of the night with a clear sexual intention, while his wife was in the room next door.”) Von Trier denied any wrongdoing, but it’s difficult not to see Dancer in the Dark through that lens now.

Clint Eastwood

The Musical: Jersey Boys (2014)

The Backstory: As a filmmaker, Eastwood has tackled lots of genres, but until his adaptation of the hit Broadway show about the Four Seasons, he’d never done a musical. (Of course, he’d been in one before, but that was a disaster.) So, why did he choose Jersey Boys? “It seemed like something to do,” Eastwood said simply, while also noting, “I did like the Four Seasons a lot. I thought their music was far superior. ‘Can’t Take My Eyes Off You’ is one of the classic songs of the era. It would have been a classic song in the ‘40s, ‘50s or ‘30s.” 

How Did It Turn Out? Even critics who dig just about anything Eastwood makes were a bit baffled: It’s not that Jersey Boys was awful, it’s just that it seemed like such a strange project for him to take on. When the movie failed to match the Tony-winning stage production’s commercial success, writers offered myriad reasons why Eastwood was the worst possible choice to adapt a jukebox musical, but you can’t deny that he made the material his own, offering a grittier, more lived-in version of the show that wasn’t just wall-to-wall tunes. And if naysayers thought he blew it, he answered his detractors by coming back just a few months later with American Sniper, which ended up being 2014’s box-office champ. 

Steven Spielberg

The Musical: West Side Story (2021)

The Backstory: “I was 10 years old when I first listened to the West Side Story album, and it never went away,” Spielberg said recently. The Oscar-winning filmmaker has done other remakes — everything from the tear-jerking Always to the nerve-shredding War of the Worlds — but taking on West Side Story is especially daunting because it’s among the most beloved of all American films. Then again, if you’re Spielberg, that’s probably part of the allure. 

How Did It Turn Out? It’s hard to take on a property that’s so entrenched in the collective consciousness, but this new West Side Story turns out to be a pretty strong adaptation. And especially in comparison to several of his colleagues on this list, this remake stands on its own as a good movie — it feels like a musical, and it feels like a Spielberg film. Other master filmmakers learned the hard way just how difficult it is to add singing and dancing to a story — Spielberg handled the task better than most.