The Best Musical Showdown

Combining the 10 musical Best Picture winners into an all-timer, super subjective game of leaderboards and winners.

Best Introduction For A Musical-Hater

If you’re trying to ease your friend who has no sweet tooth into the wondrous world of desserts, you’re probably not going to dive into the deepest corners of the cake shop’s counter. Instead, you’d go for the glistening vanilla cake or the light chocolate slices staring back at you from front and centre. The Sound of Music, the famously pleasant and digestible musical that everyone has undoubtedly seen, is that vanilla cake. That isn’t a backhanded compliment. Although it’s not impossible to criticise the film — a few critics disliked its mechanical heartiness, trying hard to offend as little as possible (hello, that’s the charm) — you have plenty of leeway to guilt your friend who openly hates this film. Besides, there’s a hefty chunk in the runtime where there’s no singing whatsoever. Win-win?

Best Musical With An Honour To Be Nominated

Ebert likened the sensations of Baz Luhrmann’s chaotically show-stopping genre revival to the unlucky predicament of being “trapped on an elevator with the circus.” I don’t know you guys, but that seems like a bit of a fun time. Moulin Rouge! is the wildest of amusement park concessions. The ride that goers whisper about with an almost cult-like obsession and a smidgen of midnight madness. If you hop on, all-knowing, your expectations will be meet with a blinding, somewhat nauseating trip, nostalgic yet tacky, but always amusing. Moulin Rouge! is the brightest diamond next to a motley of competition that doesn’t deserve my amusement park analogies. Still, the sparkle could not entice the Academy.

The Best Choreography Moments

It took a lot of willpower to not pop West Side Story into all these slots. So here is my best effort against that.

5. All That Jazz / Chicago

This whole sequence is pure gold, but the dramatic lull before the (pardon me) climatic finish, the glimpse at the Fosse hands, the fiery shoulder snap in the cop’s face, plus the final pose make this an unbeatable opening. Luckily, for the sake of Chicago, the energy persists.

4. The Dance at the Gym / West Side Story

This part would be good enough if it were just between our two supporting Oscar winners. Then Russ Tamblyn backflips into the scene and slides his partner across the floor at breakneck speed, and the scene gets an even sweeter cherry on top.

3. The Chair / An American in Paris

Forget the clash with the Hays Office over “sexually provocative” implications 🙄 (if this is the scene) because Caron proves a chair is the best support system twenty years before Minnelli’s “Mein Herr”.

2. Cool / West Side Story

West Side Story’s signature running jump is such an ingrained product of Jerome Robbin’s original vision that it has subsequently found a place in most revivals. It’s even easy to execute for the non-dancers amongst us! This scene is a detailed explosion of grief and anger that can’t be placed anywhere else but through dance.

1. America / West Side Story

Combining the costumes into the choreography is an underrated choice, and every whip and fan of those lavender and rouge dresses make the show just that little bit more inventive. Just feel sorry for the lady on the right with the slim outfit who can't have as much fun with the move as Moreno.

The Quote That I’m Most Likely To Fatigue

The songs get stuck in your head, but I'm a quote churner, and these stay on the tongue. So, I'll repeat these phrases until people beg me to stop.

5. "I'm sure that the way to say what I'd like to say will occur to me after you've gone." — Father Fitzgibbons in Going My Way. Not a fan of this film, though this is still the more sociable way of confessing that your greatest comebacks spur in the middle of showers. Although, who would I say this to? I've already stuffed up my game.

4. "There's only one business where that's no problem at all." — Velma Kelly in Chicago. Really just the way Zeta-Jones says this line. A final reminder for Academy members to check the mark next to her name and for myself to validate that she's the best best supporting actress winner.

3. "There even are places where English completely disappears; in America they haven't used it for years." — Professor Henry Higgins in My Fair Lady. Haha. Bagging Americans never gets old — take it from an Australian who uses "bag" instead of "criticise" daily. Saw a stage revival in the company of a thousand pensioners who guffawed at this remark, and a little bit of my inner oldness has laughed ever since.

2. "I'm a concert pianist. That's a pretentious way of saying I'm... unemployed at the moment." — Adam Cook in An American in Paris. Though I'm not a concert pianist. That sentiment still stings.

1. "Shut up and drink your gin!" — Fagin in Oliver! A gin + tonic is my go-to alcoholic drink, so if I hit the town with Fagin, I'd probably shut up and drink up, so long as he'd repeat the favour.

Most Misunderstood Winner

Chicago, which appears on one too many “worst Best Picture” lists, gets far too much flack for its worth. Sure, it’s an unlikely winner pushed by Miramax’s final blitz against a sea of great to mediocre competition that could barely gain a leg, but who would you choose instead? If it weren’t for Chicago, I’d go for The Hours. Regardless, Chicago is still one of the finest winners from that decade. It’s one of the best-edited musicals, filled with an iconic slate of performers, revamps the original soundtrack with all the brass in the world, and plays into the show-within-a-show trope to perfection. Now, if people would stop letting WatchMojo infiltrate their bias.

The Best Outfits

Seven of these Best Picture winners were nominated for their costume design, while five also won. This gallery knows that the best outfits aren’t always confined to that category and is open to all. I just wanted the chance to show off The Great Ziegfeld’s showboat wardrobe.

Top L to R: The Sharks (West Side Story); Eleanor Parker (The Sound of Music); Eliza’s B&W Ascot gown (My Fair Lady). Centre L to R: Eliza’s Embassy Ball gown (My Fair Lady); Leslie Caron’s yellow ‘50s silhouette (An American in Paris); Leslie Caron’s timeless floral dress (An American in Paris). Bottom L to R: Roxie shows off her inner showgirl (Chicago); Caron is back with a B&W gown to rival Ascot (Gigi); Just one of plenty ridiculously exuberant gowns to prove the namesake’s eccentricity (The Great Ziegfeld).

The Stickiest Songs

These are all super catchy, live rent-free upstairs, and are also pretty awesome show-tunes to boot. So take this as my unofficial, official ranking.

10. "Pick a Pocket or Two” / Oliver!

9. "Wouldn't It Be Loverly?” / My Fair Lady

8. "My Favorite Things” / The Sound of Music

7. “I Can’t Do It Alone” / Chicago

6. “Roxie” / Chicago

5. “Oom-Pah-Pah" / Oliver!

4. "I Feel Pretty” / West Side Story

3. "Cell Block Tango” / Chicago

2. "When You're Good to Mama” / Chicago

1. "America" / West Side Story

The Best Musical Moments In Non-Musical Best Pictures

5. And The Band Played On / Titanic

4. “Jai Ho” / Slumdog Millionaire

3. Waltz / The Godfather

2. “You’ll Never Know” / The Shape of Water

1. “La Marseillaise” / Casablanca

The One I’m Least Likely To Recommend

Okay, maybe I would recommend, but only with a reasonably clear disclaimer. No new technology comes easily, and it’s convenient to scoff with the retrospection of almost a century. However, The Broadway Melody is still a wobbly foray into a new medium and a boringly dire slog. It is utterly devoid of the legendary MGM musical charm. Even if then-contemporary audiences might have marvelled at the exhibit, viewers today might be left cold. See it as an essential aspect of film history rather than a slice of entertainment, and you might find a glimmer of satisfaction. Unfortunately, for most modern-day audiences, the appeal of “all-talking, all-singing, all-dancing” fanfare, especially one that has been succeeded by hundreds more superior, does not strike with the same tempt of that 1929 slogan.

The One I’m Most Likely To Recommend

West Side Story is an imperfect film that feels perfect. It’s worth saying that the drama, and the dialogue, in particular, are nowhere near as divine as Jerome Robbins’ choreography. The musical numbers, best described as “energetically blocked,” are the best on film. It’s also worth letting people indulge in the best that musical numbers can be — start high because most of the time, it’s only downhill from here.

Qualifying To Grand-Final Pipeline

Combining all the musicals ever nominated for Best Picture into a pipeline of competition and a ton of subjectivity. The first list was randomised, and for all rounds, I work from top to bottom. Face-offs with the victors in bold until we have my winner. A pretty simple task, ruffled by an odd amount (39) of films.

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