Only 10 musicals have ever won the Oscar for Best Picture, and some have stood the test of time better than others. The first musical to win Best Picture was The Broadway Melody, which won at the second-ever Academy Awards. Back then, the prize was called "Outstanding Picture". The awards have changed a lot over the years, but musicals have still managed to achieve occasional success. The 1950s and 1960s saw a string of musical winners, but more recently the Academy has developed different tastes.

There has only been one musical winner of Best Picture in the last 50 years, showing the way the genre has fallen out of favor. However, with Emila Perez and Wicked up for the top prize, musicals can break through with Academy voters. The Oscars aren't the perfect indicator of film quality, and as such, these 10 Best Picture winners are not necessarily the best musical movies of all time. Classic musicals like Singin' in the Rain and Cabaret have failed to win the top prize. However, with the statue won, these musicals are certain standouts in the genre.

10 The Broadway Melody (1929)

The First Movie With Sound To Ever Win The Academy's Top Prize

Just a year after the Academy Awards held their first ceremony, The Broadway Melody won the Oscar for Outstanding Picture. It was the first "talkie" to win the award since the very first winner was the silent movie Wings. The Broadway Melody was also the first talking musical released by a major Hollywood studio, so it represented the pinnacle of technical achievement at the time. By today's standards, The Broadway Melody is rather flat and lifeless.

The Best Picture win can be chalked up to audiences being wowed by a movie that featured song and dance numbers like never before. However, the other aspects of the film showcase how Hollywood was still moving out of the silent era and there were plenty of growing pains to deal with, from awkward performances to a flimsy story. It deserves its place in movie musical history, but it has been sured to the point of redundancy in the years since. Along with Best Picture, The Broadway Melody was nominated for Best Director and Best Actress.

9 Going My Way (1944)

Bing Crosby's Soothing Voice Is Not Enough To Lift A Mediocre Plot

Bing Crosby won Best Actor for Going My Way, a story about the inter-generational divide between two priests. Crosby plays the young upstart who comes in to take over from an older priest who sticks to the traditions of the church. Crosby's five songs are all sung beautifully.

Even though they aren't among his greatest hits, he has an endearing sweetness that helps lift the movie whenever it threatens to stray into overly tedious dialogue. The movie showcases the quieter musicals that were also popular at the time, which didn't have elaborate musical set pieces, but simply infused songs into the story.

Crosby was also nominated for his performance in the sequel, The Bells of St. Mary's, which came out the following year. Notably, Going My Way is also the first Best Picture winner to get a sequel. The movie was a huge hit at the Oscars, earning 10 nominations in total, winning seven of them.

8 The Great Ziegfeld (1936)

Outrageously Opulent But Overly Long

The Great Ziegfeld was produced during the early days of movie musicals, and it retains a lot of the conventions of the stage. Some of its biggest musical numbers seem like lavish stage productions, but they rarely take advantage of the possibilities of film. The biopic of Broadway producer Florenz Ziegfeld Jr. seeks to drown its audience in sequins and feathers, and it does so for a bloated three hours. At the time, it was the longest talking movie ever made.

There are some highlights along the way, but the curtain should have dropped on this tribute to Broadway much sooner. Some ludicrous overacting doesn't help matters. Its Best Picture win not only highlights the Academy's early love of lavish musicals, but also its love of biopics which hasn't faded much over the years. The Great Ziegfeld was nominated for seven Oscars in total, winning three, including the now-forgotten category Best Dance Direction.

7 Gigi (1958)

Gigi Is Visually Stunning, But Its Plot Is Uncomfortable

Gigi kicked off the most successful run that movie musicals have ever had at the Oscars. Including Gigi, five of the next eleven winners of Best Picture were musicals. Unfortunately, these movies all got better after Gigi. Gigi is based on the French novel of the same name by Colette.

The plot has some very uncomfortable moments by today's cultural standards, and the sudden switch toward charming musical numbers can be very jarring.

It follows a young woman who is groomed to become a courtesan until she meets a wealthy man named Gaston. The plot has some very uncomfortable moments by today's cultural standards, and the sudden switch toward charming musical numbers can be very jarring.

Gigi looks great and director Vincente Minnelli had proven himself in the musical genre, staging effective set pieces. However, it is just not an easy movie to get into as it has aged so poorly. However, subject matter aside, looking back on Gigi, it feels like a lesser imitation of many of the better musicals of the era.

6 Oliver! (1968)

A Charming Romp Through Dickensian London

From Les Misérables to The Color Purple, there have been a number of classic novels that have been turned into musicals. Based on the novel Oliver Twist by Charles Dickens, Oliver! tells the story of a Victorian street urchin who is taken in by a gang of thieves in London before discovering his true parentage. As with most Dickens stories, it's a class-conscious fable about fate and determinism in a cruel world, but Oliver! has an upbeat ending.

It's one of the best movies based on Dickens, as the music enhances the emotion of the story. "Food, Glorious Food" is perhaps the most enduring number, but Kathe Green (who dubbed all of the vocals for Mark Lester, the actor playing Oliver) also helps "I'd Do Anything" and "Where Is Love?" stand out. The movie was a huge hit with the Academy, earning 12 nominations and winning six, including an honorary award for its choreography.

5 Chicago (2002)

The Most Recent Musical To Win Best Picture Is Stylish, Raunchy, And Undeniably Fun

The most recent movie musical to win Best Picture was Chicago, starring Catherine Zeta-Jones and Renée Zellweger in excellent form as two women being tried for murder. Based on the hit Broadway show of the same name, the story follows the media circus that results from the trial and how these women and a smooth-talking lawyer are about to manipulate the public through the press.

Chicago revels in its roots as a stage musical, with the film version enhancing the stagecraft and performances but never distracting from them. "All That Jazz" and "Cell Block Tango" are the two outstanding musical numbers.

Chicago ended a long wait for a Best Picture win for a musical, and it could be just as long before the next one based on recent Oscar trends. Bringing this kind of lavish, Broadway-inspired production back to the movies was something the Academy was clearly waiting for, earning 13 nominations and six wins.

4 An American In Paris (1951)

Gene Kelly Is A Joy To Watch In This Beautiful Romance

An American Paris was the first of two musicals directed by Vincente Minnelli to win Best Picture, seven years before Gigi. It also starred his Gigi leading lady, Leslie Caron, but made for a much more effective musical. Gene Kelly is the titular American, a painter who falls in love with a French woman while visiting Paris. Their romance becomes complicated by the fact that his friend falls in love with the same woman.

The movie makes good use of Kelly's charisma and his legendary dancing skills. The only thing that holds An American in Paris back is its relative lack of memorable songs. The finale is an extended dream-like sequence with elements of ballet set to George Gershwin's orchestral piece, An American in Paris. The movie was nominated for eight Oscars and ended up winning six of them.

3 My Fair Lady (1964)

Audrey Hepburn Blends Comedy And Glamour In Her Portrayal Of Eliza Doolittle

Julie Andrews starred in the stage version of My Fair Lady, but Audrey Hepburn stepped in to replace her for the movie. The movie is based on the classic novel of the same name by George Bernard Shaw and tells the story of an arrogant professor who makes a wager that he can turn even the roughest of common girls into a member of high society.

Hepburn's voice was dubbed over by Marni Nixon for all but one of her songs. This decision outraged her at the time, but it proved to be a great choice for the movie. Hepburn may not be the best singer, but her portrayal of Eliza Doolittle is colored by her inimitable charm. My Fairy Lady is one of Audrey Hepburn's best movies, containing many of her most iconic on-screen looks to accompany the brilliant soundtrack. The movie was nominated for 12 Oscars and won eight.

2 West Side Story (1961)

Leonard Bernstein's Music Gets A Fitting Movie Adaptation

Although Steven Spielberg's 2021 adaptation was a surprise hit with critics, it's the 1961 version of West Side Story which won Best Picture. Based on Shakespeare's Romeo and Juliet, West Side Story takes the story of the Montagues and Capulets and transplants it into a tale of gang violence in New York City.

West Side Story's darker tone was a hit with critics and audiences alike, while it helped to introduce many of the iconic songs from the Broadway musical to the mainstream.

It follows a young member of a street gang who falls for the sister of one of his rivals, defying those around them with their romance. The stage musical was written by Leonard Bernstein and Stephen Sondheim, and it marked a turning point in the development of American musicals.

The movie was just as revolutionary. West Side Story's darker tone was a hit with critics and audiences alike, while it helped to introduce many of the iconic songs from the Broadway musical to the mainstream. The movie was nominated for 11 Oscars and won all but one of them.

1 The Sound Of Music (1965)

An Uplifting Classic With An Unbeatable Soundtrack

Julie Andrews shot to fame with her starring role in Mary Poppins, and she followed it up with an equally iconic performance in The Sound of Music a year later. She plays Maria, a governess who moves in with a musical family in Austria just before the outbreak of the Second World War. It's a sumptuous adaptation of the Rodgers and Hammerstein musical.

The Sound of Music's soundtrack is iconic, with hits such as "My Favorite Things," "Do-Re-Mi" and, of course, the title track. The Sound of Music rightly won Best Picture, and Andrews can consider herself unlucky for missing out on Best Actress. Along with winning five Oscars out of ten nominations, the movie has been hailed as one of the best of all time. It continues to be rewatched by fans decades later with the music becoming part of pop culture.

The Sound of Music won Best Picture directly after My Fair Lady. This is the only time in the history of the Academy Awards that two musicals have won Best Picture back-to-back.