No movie genre is more misunderstood than the musical. To many, musicals are the epitome of cinematic showmanship, disposable entertainment meant to be enjoyed by turning off one’s brain and indulging in the inherently silly premise of people randomly bursting into song when the mood strikes. And you know what? There is something to that notion; indeed, many movie musicals are silly and proud of it. There’s nothing wrong with a silly musical, but the genre is far more than that.

Nowhere is the genre’s complexity more evident than in its history of rich characters. The musical has been around pretty much since the advent of sound cinema, meaning there’s almost a century of wonderful musical characters to choose from for this list. We are ranking the all-time best musical characters in cinematic history, and the range included will convince anyone of the embarrassment of riches within the genre. From singing nuns to vaudevillain killers, these cinematic figures can light up the screen while belting out an E5.

10

Satine (Nicole Kidman) – ‘Moulin Rouge!’ (2001)

Image via 20th Century Studios

The movie musical was all but dead going into the new millennium. If it was going to ever come back, it needed a serious jolt, the kind Frankenstein used to reanimate his monster. Luckily for the genre, Baz Luhrmann stepped in to become cinema’s version of the doctor, delivering the messy and electrifying triumph that is 2001’s Moulin Rouge! The film is a jukebox musical about the doomed affair between a courtesan and a poet in the final year of the 19th century.

In a career-defining role, Nicole Kidman plays Satine, the cynic and pragmatic courtesan with a death sentence. Satine is a challenging role; as the ultimate courtesan, she must be simultaneously outgoing and reserved, seductive but elusive, guarded but vulnerable. Kidman makes a meal of the role, delivering an unrestrained, courageous performance that rightfully earned her an Oscar nomination and forever altered the course of her career. Moulin Rouge!‘s maximalist approach is not for everyone, and it could easily fall apart under the weight of its sheer excess. It’s Kidman who grounds it and keeps it from becoming caricature, striking the right balance between camp and sincerity.

9

Willy Wonka (Gene Wilder) – ‘Willy Wonka and the Chocolate Factory’ (1971)

Image via Warner Bros.

Gene Wilder famously invited you to a world of pure imagination in 1971’s Willy Wonka and the Chocolate Factory. Sure, that world turned out to be more the nightmare of a slightly deranged man-child, but it had its charms if one knew where to look for them. The point remains that Wilder’s take on the zany chocolatier is one of cinema’s greatest comedic turns, a perfect combination of “eerie” and “charming” that remains the standard.

It’s hard to do what Wilder does as Willy Wonka, and harder still to make it seem effortless. The great strength in his performance is that he allows the wackiness to speak for itself; rather than trying to seem crazy or going for broke, Wilder allows Wonka’s eccentricities to shine through. His mannerisms are controlled, but his eyes are wild, piercing through his guests, enjoying their comeuppances but never cackling at them. Take his now iconic entrance: he limps, he pretends to fall, then he somersaults. It’s memorable and incredibly fun, but never exaggerated, naturalistic comedy at its finest and a testament to how much of a genius this man was when in his element.

8

Esther Blodgett/Ally Maine (Judy Garland, Barbra Streisand, Lady Gaga) – ‘A Star Is Born’ (1954, 1976, 2018)

Some stories are timeless, inspiring countless retellings, each offering something new about both the story itself and the societal context in which it was made. A Star Is Born is one such story, with the original 1937 film inspiring three musical remakes, each one great in its own way. The skeleton of all movies is the same: a successful man discovers and falls in love with a woman of extreme talent. Their relationship ends in tragedy due to his excesses and inability to cope with her rising success.

All versions of A Star Is Born are elevated by a tour de force female performance at its center. Three of those versions are musicals, and all three have an icon playing the talented Esther Blodgett (or Ally in 2018). In 1954, Judy Garland delivered what can only be described as one of cinema’s all-time greatest one-woman shows. The story of addiction and struggle painfully mirrored her real life, giving a layer of raw authenticity to her work that has ultimately made it timeless. In 1976, Barbra Streisand played Esther as a rebel in a rock-and-roll world, far more persistent but no less resilient. Finally, in 2018, Lady Gaga played Ally, more wide-eyed and vulnerable but also more human, less a star and more an idol. Each depiction provides something different, proving that Esther is one of cinema’s most malleable characters, a true shapeshifter who can be multiple things at once.

7

Eliza Doolittle (Audrey Hepburn) – ‘My Fair Lady’ (1964)

Image via Paramount Pictures

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My Fair Lady taught us two things: one, the rain in Spain stays mainly in the plain, and two, Audrey Hepburn could really do no wrong. Taking on the role famously originated and, it must be said, perfected by Julie Andrews on the stage was no easy task, but Hepburn rose to the challenge. Yes, her singing was dubbed by classic Hollywood’s most famous ghost singer, Marni Nixon, but Hepburn’s take on Eliza Doolittle is no less impressive.

Eliza is not an easy role to play. Her naiveté can be tricky and, in the wrong hands, come across as annoying. Yet, Hepburn is delightful in the role, injecting so much enthusiasm into her portrayal that one can’t help but surrender to her charms, much like Professor Higgins himself. Hepburn is a blast throughout — the physicality, the exaggerated accent, the willingness to (figuratively) fall flat on her face, it all amounts to one of cinema’s most fully-embodied comedic turns. In her hands, the word “influenza” pretty much becomes both joke and punchline simultaneously. In My Fair Lady, Hepburn gives a masterclass in humorous escalation that remains as delightful as it is enchanting. By George, she’s got it!

6

Velma Kelly (Catherine Zeta-Jones) – ‘Chicago’ (2002)

Image via Miramax

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Catherine Zeta-Jones won an Oscar for Chicago, and I’m convinced it was largely because of her delivery of the word “Cicero.” As the vaudevillian songstress and murderess Velma Kelly, Zeta-Jones is explosive and tantalizing, almost single-handedly bringing sexy back to the musical genre after decades of stillness. Chicago reworks the musical, focusing on Roxie Hart (Renée Zellweger) and making Velma a large role in her story. However, that approach only allows Zeta-Jones to become the ultimate scene-stealer.

Indeed, Roxie might be the lead, but Velma is the star. From the second she appears on the screen, delivering a seductive and invigorating rendition of “All That Jazz,” Velma commands our attention, and we have no choice but to acquiesce. Zeta-Jones famously agreed to play Velma just so she could sing “All That Jazz” — and insisted on the short wig to make sure everyone saw it was actually her doing all the dancing and singing — and there has seldom been a better match of a perfect role going to the perfect actress. Chicago is arguably the best movie musical of the 21st century, and a large reason for its success is Catherine Zeta-Jones. She is jazz embodied: chaotic, full of life, slightly dangerous, and simply irresistible.

5

Dorothy Gale (Judy Garland) – ‘The Wizard of Oz’ (1939)

Image via Loew’s, Inc.

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From the moment Judy Garland appears in the black-and-white Kansas portion of The Wizard of Oz, one instantly understands they’re in the presence of a generational talent. As soon as she belts out “Over the Rainbow,” all doubts are gone, and there’s not a dry eye in the house. Garland is instantly captivating as Dorothy Gale, effortlessly embodying the innocence necessary for such a role and blending it with the wide-eye enthusiasm that can only come from raw talent.

The stories of the cruel treatment Garland endured in the set of The Wizard of Oz are infamous and the stuff of Hollywood nightmares. Knowing that, and knowing what would eventually happen to Judy, makes the experience bittersweet for sure. And yet, Judy is so pure, so endearing as Dorothy that one can forget the harshness and get lost in the wonder of Oz. A movie like The Wizard of Oz relies entirely on our ability to suspend disbelief and surrender to the wacky antics on the screen. Judy is crucial to that immersion; it is through and because of her that we become willful spectators in this wonderful world. She is the audience surrogate, making it extremely easy to follow the yellow brick road.

4

Donald “Don” Lockwood (Gene Kelly) – ‘Singin’ in the Rain’ (1952)

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Widely considered an institution of American cinema, Singin’ in the Rain is one of the great triumphs of the seventh art. Set during the transition of silent cinema to sound, it depicts a longtime acting pairing who must deal when only one of them has the voice to perform in a musical. Gene Kelly leads the cast as Donald “Don” Lockwood, a former silent star and the living embodiment of having a song in your heart.

There’s a reason why Singin’ in the Rain has such a reputation as being the apex of the musical genre; if any movie qualifies as joy captured on celluloid, it’s this one. Kelly is integral to that success, playing Don as the ultimate song-and-dance man. Every moment he’s on screen is unforgettable, but his now-iconic performance of the titular song has become quite possibly the most recognizable moment in the musical genre. Kelly was one of a kind when it came to staging a number, and he’s at the peak of his abilities in Singin’ in the Rain. Words cannot do justice to his work; indeed, his is a performance that needs to be experienced. What a glorious feeling, indeed.

3

Maria von Trapp (Julie Andrews) – ‘The Sound of Music’ (1965)

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How do you solve a problem like Maria? In 1965, The Sound of Music took the world by storm. The story of a jolly nun with a divine voice who becomes the governess of a group of seven Austrian children and eventually marries their widowed father captivated audiences, grossing $287 million. Adjusted for inflation, The Sound of Music grossed more domestically than Avatar, currently the highest-grossing movie. To call it a phenomenon would be a disservice.

At the heart of it all is a truly spectacular Julie Andrews as Maria von Trapp. Her divine voice elevates standards like “My Favorite Things,” “Do-Re-Mi,” and the titular song, injecting a sense of pure, gleeful charm into tunes that are already pretty perfect compositions. There’s not an ounce of ego or pretension in Andrews’ performance, just a sense of genuine enthusiasm, an unadulterated and sincere passion that makes even the cheesiest lyrics seem like absolute life certainties. In the process, Andrews herself becomes timeless, her work an ode to the joy of music and a testament to the musical genre’s power to transport and enthrall.

2

Fanny Brice (Barbra Streisand) – ‘Funny Girl’ (1968)

Image via Columbia Pictures

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Hello, gorgeous, indeed. From the second Barbra Streisand steps into the scene as the young ingenue Fanny Brice, audiences knew that a star was born. Reprising the role she originated on Broadway, Streisand was a dynamo in Funny Girl, lighting up the screen with charisma for days and a now-iconic voice that could bring even the staunchest musical hater to tears. Belting out numbers like “Don’t Rain on My Parade” and “My Man,” Streisand became an instant icon.

For her efforts, Streisand won the Oscar for Best Actress, famously tying with Katharine Hepburn. It’s not hard to see why Fanny so transfixed audiences: Streisand is simply spectacular, a ball of energy and charisma, a great big clump of talent. To this day, the role of Fanny is closely related to Streisand, and always will be. The actress defined Fanny for an entire generation, but it’s her voice — the legendary, beautiful vibrato, the pristine technique, the powerful belt that seems to transcend the screen — that made Funny Girl a hit. She is the greatest star, and almost sixty years later, no one has even come close to her standard.

1

Sally Bowles (Liza Minnelli) – ‘Cabaret’ (1972)

Image via Allied Artists Pictures

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I’d argue that perhaps no musical role is as synonymous with the genre as that internazionale sensation, Fraulein Sally Bowles. Played to perfection by an incandescent Liza Minnelli in the role that won her an Oscar, Sally is a free-spirited and willingly naive young woman and the main attraction at the Kit Kat Club in 1931 Berlin. Set against the rise of the Nazi party, the film chronicles Sally’s bohemian life and her affair with British scholar and writer Brian (Michael York).

Cabaret is an intense masterpiece of the musical genre, filled to the brim with decadent, exuberant numbers, perfectly staged by the master himself, Bob Fosse. However, it’s also a remarkably dark work, a sardonic look at how easy it is for injustice and cruelty to take over; all it needs is a captive audience. Thus, Sally Bowles is the embodiment of complicity, representing everyone who has ever stayed quiet, preferring contentment over struggle. Sally is willfully blind, joyously ignorant; after all, from cradle to tomb, it isn’t that long a stay. Cabaret is a harsh critique of the inability to act, and it casts the greatest star of her generation to enthrall the audience into going along with its spell — and it works. In the end, life is a cabaret, and Liza is the ultimate headliner.