In the history of the Academy Awards,only 10 musicals have ever won the top prize of Best Picture, and only one was released post-1968. That might be enough to signify that the musical genre was at its peak a decent number of decades ago. But, then again, other musicals have proven successful at the Oscars,includingCabaret, which won eight Oscars(but lost Best Picture toThe Godfather), andLa La Land, which won several Oscars and, for a few brief moments,seemed like it had won Best Picture(Moonlightwas the actual winner).
But rather than focusing on those musicals that came close to winning Best Picture, what follows is a ranking of the 10 that did indeed win that top prize. Some are still considered great to this day, while other lesser winners were certainly products of their time. Nevertheless, they all won the top prize at the Oscars and are ranked below from “forgettable” to actual cinematic masterpieces.
10’The Broadway Melody' (1929)
Director: Harry Beaumont
Some would sayThe Broadway Melodyis a contender for the title ofworst Best Picture winner of all time, and after watching the film, it’s not hard to see why. It was something that admittedly was inherently limited by the technology of its time—dialog in film was still close to brand new in 1929—but even then, it’s pretty rough to try and sit through, regardless of how much you usually like 1920s movies.
It’s a convoluted melodrama set on Broadway, with far too many characters and perhaps too few compelling musical numbers to distract from all the uninteresting drama. It might’ve been impressive for viewers seeing it in 1929, butThe Broadway Melodyis honestly kind of unwatchable today, unlikecertain classics from the 1920swhich do still hold up.
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9’The Great Ziegfeld' (1936)
Director: Robert Z. Leonard
IfThe Broadway Melodywas the first and worst musical to win Best Picture at the Oscars, then the second musical to win that prize,The Great Ziegfeld, is the second-worst, appropriately enough. It’s an early biopic of sorts, centering onFlo Ziegfeld, a prominent Broadway producer whose revues were popular throughout the 20th century’s early decades.
It impresses a little more when it comes to musical numbers, compared toThe Broadway Melody, butthe big thing that significantly holdsThe Great Ziegfeldback is its ridiculous length. Surprisingly and inexplicably,the film goes for over three hoursand really doesn’t feel like it needs much more than half that runtime to tell its story. Thus,The Great Zigfieldis a difficult Best Picture winner to try and endure, lacking the spectacle of future musical efforts and the compelling story to justify its bloated runtime.
8’Gigi' (1958)
Director: Vincente Minnelli
If technical limitations were the main obstacle for enjoyingThe Broadway Melody, and a bloated runtime was the main reasonThe Great Ziegfeldwasn’t great, thenGigi’s single biggest sin isthe fact that it’s aged very badly. The plot follows the unexpected romance between the sweet and inexperienced Gigi and the roguishly charming Lothario Gaston.
Gigican make for an oddly uncomfortable watch, presenting awkward songs and tone-deaf messages within the confines of a breezy/romantic/comedic story. It’s all distinctly old-fashioned in a way that might’ve even felt old-fashioned by the standards of the 1950s.Gigiwon big for its year of release, but beyond some of its technical qualities and the colorful visuals, there isn’t a great deal aboutGigithat feels endearing or engaging when watched today.
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7’Oliver!' (1968)
Director: Carol Reed
Make no mistake:Oliver!might center on various youthful characters, but it really doesn’t feel very family-friendly. The plot centers on the misadventures of orphan Oliver Twist, who becomes involved with a band of pickpockets led by the Artful Dodger.It’s a rather jarringly dark musical, and though the source material byCharles Dickenswas also more than a bit grim, the bleaker aspects of the story clash with the often jaunty, earworm songs.
Still, for those who know what they’re in for,Oliver!is a decent watch and an interesting adaptation of Dickens’s storytold in musical form. It’s also notable for being the final musical released in the 20th century to win Best Picture, and, to date, is still the second most recent musical to win the top award, which reveals much about the genre’s state in the New Hollywood age.
6’Going My Way' (1944)
Director: Leo McCarey
A relatively inoffensive blend of musical, comedy, and drama,Going My Wayis perhaps one of the least well-known Best Picture winnersin Oscar history. It’s not undeserving of such a fate because there are far more noteworthy winners, both within and outside of the musical genre, but it’s also far from bad for its time.
It follows a priest, played byBing Crosby, who arrives at a parish and inspires a group of troubled boys, thanks to his youthful spirit and ability to see eye to eye with those from younger generations.Going My Wayis formulaic and a touch too sentimental, in line withother post-World War II movies. However, it’s still pretty watchable overall, ticking all the boxes it needed to by the standards of mainstream cinema back in the mid-1940s.
5’My Fair Lady' (1964)
Director: George Cukor
The 1960s was perhaps the decade where the musical genre was at its best and most popular, with four Best Picture winners from that decade belonging to the genre. For comparison, the only other decade with more than one musical Best Picture is the 1950s. As such, it’s not too surprising to seeMy Fair Ladybe a musical Best Picture winner that wasreleased at about the mid-point of the decade.
Its story is rather conventional for a movie that stretches to almost three hours, but it houses an iconicAudrey Hepburnperformance, looks great visually, and contains some memorable music numbers. Its behind-the-scenes drama is also the stuff of Hollywood legend, from casting controversies to voice dubbing and other machinations courtesy of Jack L. Warner. Still,My Fair Ladyremains a classic of 1960s cinema, and while some aspects have aged like milk, the film itself holds up quite well.
My Fair Lady
In 1910s London, snobbish phonetics professor Henry Higgins agrees to a wager that he can make crude flower girl Eliza Doolittle presentable in high society.
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4’The Sound of Music' (1965)
Director: Robert Wise
Just one year afterMy Fair Ladywon Best Picture,The Sound of Musicdid the same, making this the only time two musicals won the main award at the Oscars two years in a row. It’s also comparable toMy Fair Ladyin that it’s very long, falling shy of three hours by just six minutes. Based on Maria Von Trapp’s 1949 memoirThe Story of the Trapp Family Singers, the film follows Maria, a nun who becomes governess to seven children before marrying their father.
Suitably epic for something of such a length,The Sound of Musictells a large-scale story that spans genres, feeling like a family film, a romance, and a pre-WWII movie, all on top of being a musical. It’s also rightly celebrated for the lead performances fromJulie AndrewsandChristopher Plummer, both of whom are at their respective peaks here. Now widelyconsidered among the all-time best musicalsand one of the most undeniable Best Picture winners,The Sound of Musicis a masterpiece of the genre and one of the highest-grossing films ever. Not bad for a singing nun!
The Sound of Music
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3’An American in Paris' (1951)
An American in Pariswas the first musical shot in color to win Best Picture at the Oscars. Its use of the then-groundbreaking technique is perhaps the thing that stands out the most about it. It’s one of the most visually pleasing musical films of all time, with fantastic costumes and sets all captured extremely well by directorVincente Minnelli, who won the Best Director Oscar for 1958’sGigi,which, for all its faults, did at least look good).
The romance story here is light and silly, butAn American in Parisdoesn’t take itself too seriously and keeps things mostly breezy and comedicthroughout. It benefits greatly from both its leads,Gene KellyandLeslie Caron. The pair is the embodiment of charm, rhythm, and old Hollywood glamour, forming one of cinema’s most unforgettable pairs. Thefilm saves the best for lastwith a stunning and dreamlike climactic sequence that remains celebrated today.
An American in Paris
Three friends struggle to find work in Paris. Things become more complicated when two of them fall in love with the same woman.
2’Chicago' (2002)
Director: Rob Marshall
It’s good thatChicagowon Best Picture at the Oscars because it truly wasone of the best movies released in 2002. It’s a comedic crime musical where much of it’s set inside a female prison—specifically death row, where two women, Roxie Hart and Velma Kelly, are willing to do whatever they can to make a scene and survive upcoming scheduled executions.
A sharp, witty, largely fun take on its various genres, the film has some sharply satirical things to say about fame and the justice system. Energetic, sexy, and full of explosive musical numbers,Chicagois a triumph that single-handedly revitalized the then-dying musical genre. It’s so good that it’s managed to be the only musical to win Best Picture after a 34-year dry spell for the genre. Hopefully, musical fans won’t have to wait 34 years to see another musical crowned Best Picture.
Two death-row murderesses develop a fierce rivalry while competing for publicity, celebrity, and a sleazy lawyer’s attention.
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1’West Side Story' (1961)
Director: Robert Wise, Jerome Robbins
Though it was remade bySteven Spielberg(compellingly so) in 2021, it still feels like 1961’s version ofWest Side Storyis the definitive film musical in American cinema. It expertly updatesRomeo & Juliettoset it during a then modern-day gang war, helping this musical feel sweeping, romantic, exciting, epic, and tragic all at once.
West Side Storykick-started the run of musical Best Picture winners in the 1960s and was arguably the best of the bunch. It hasn’t aged perfectly, and some may prefer the 2021 version, but for its time,1961’sWest Side Storywas just about as moving and thrilling as large-scale movie musicals got, guaranteeing its status as a classic.
