30. “High Society” (1956)
The consensus on release was that “High Society” was a fun but inferior remake of the comedy classic “A Philadelphia Story” (released only 16 years beforehand). We’d acknowledge that it perhaps isn’t quite as tremendous, but now, it stands up beautifully: a witty, joyful, featherlight musical comedy full of great performances. The plot is roughly the same: A divorcé (Bing Crosby) tries to win back his ex (Grace Kelly) on the eve of her wedding, while a journalist (Frank Sinatra) sent to cover the nuptials also falls for her. With Louis Armstrong acting as a sort of Greek chorus, it has a killer selection of Cole Porter numbers, this being his first original score in eight years, including “Who Wants To Be A Millionaire” and “True Love,” delivered with effortless cool by the ace cast (also including Celeste Holm).
Best Number: Uniting Bing Crosby and Frank Sinatra was a sort-of musical version of the coffee-shop scene from “Heat,” and “Well Did You Evah!” lives up to the billing.
29. “Meet Me In St. Louis” (1944)
Less a really strong narrative than a series of little lessons in life and acceptance, lifted out of after-school-special moralism by the gorgeous Technicolor photography, period detailing and one of Judy Garland‘s most endearing performances, “Meet Me In St. Louis” is yet another triumph for director Vincente Minnelli (and he met future wife Garland on the set). A nostalgically fond portrait of family contentment briefly threatened then reestablished, its low-stakes, rose-tinted view of life, love and St. Louis just before the World’s Fair is deeply, unapologetically sentimental, but sometimes that’s exactly what you want from a musical.
Best Number: Bending our own rules a little bit here — we should choose “The Trolley Song” as that is the bigger, fizzier number, but Garland’s brokenhearted rendition of “Have Yourself A Merry Little Christmas” is just sublime, and lends the picture what little grit it has.
28. “Gentlemen Prefer Blondes” (1953)
An interesting development in recent years has been the reclamation of Howard Hawks‘ classic Jane Russell/Marilyn Monroe vehicle as a queer-cinema cornerstone: Such analyses point to the way that though the film’s plot revolves around their marriage prospects (and Russell’s character especially is portrayed a voracious maneater), the defining relationship is between the two women. This is an especially welcome development for those of us who always loved the film in spite of its regressive politics, but the manhunting/gold-digging that the film follows is so acidly observed (credit the original book’s writer, the wonderful Anita Loos), and the songs so sharp and knowing, that it has always felt a little subversive. Russell is sassy, world-weary and wise, Monroe is the archetypal ditz, yet the “Two Little Girls From Little Rock” (the movie’s best duet) share a fierce loyalty to each other and a hard-headed pragmatism towards men that makes them nobody’s fools.
Best Number: “Diamonds Are A Girl’s Best Friend,” of course — and don’t get so distracted by Monroe’s delicious wiggle that you fail to admire the absolute genius rhymes in this song (“Stiff back or stiff knees, you stand tall at Tiff’ney’s” is a particular favorite).
27. “Phantom Of The Paradise” (1974)
Quite rightly, the rock opera is something that inspires fear in most sensible people, but the single greatest film example is Brian De Palma’s “Phantom Of The Paradise.” At once utterly different and of a piece with the rest of the director’s filmography, it reboots the classic horror tale of “The Phantom Of The Opera” (later given a dire musical reboot by Andrew Lloyd Webber) for the glam-rock era with songs by Paul Williams (who also stars). Campy, horrific, hilarious, genuinely suspenseful (there’s a cracking split-screen sequence) and influential to a degree beyond the number of people who’ve seen it, it’s a true piece of pop art, and deserved to be the kind of cult smash that “The Rocky Horror Picture Show” became the following year. Hopefully, its time is still to come.
Best Number: The songs are all great, but “The Hell Of It” might be our fave.
26. “Enchanted” (2007)
There are only five songs in Kevin Lima‘s delightful parody of/homage to the Disney princess genre, but, written by Disney maven Alan Menken and Stephen Schwartz, and sung so sweetly by a brilliant, breakout Amy Adams, they’re more than enough to qualify this film for a spot here. Really one of the most surprisingly lovable and witty family films of the last decade, “Enchanted” follows Giselle (Adams), a princess cast out of her 2D, traditionally animated home and into the real world, by the evil mother (a deliciously slavering Susan Sarandon) of her betrothed Prince (a hilariously game James Marsden). She’s taken in by Patrick Dempsey‘s pragmatic single father to somewhat predictable ends, but it’s Adams’ brilliant reactions, her guileless transparency and her weirdly uncloying sweetness that makes “Enchanted” the gently progressive Disney Princess movie it is.
Best Number: Not our favorite song, but for sheer scale and exuberance, “That’s How You Know” has to take it.
25. “Cabin In The Sky” (1943)
The second, and far superior, black musical released in 1943 (see “Stormy Weather“) also stars Lena Horne, but this time actually boasts a story, and an original one at that. Vincente Minnelli lends his graceful direction to this tale of the angels of heaven and the demons of hell battling for the soul of one wastrel gambler, Little Joe (Eddie “Rochester” Anderson), whose apparent only redeeming characteristic is that his loving wife Petunia (Ethel Waters, radiant) prays so hard for him. Horne is Georgia Browne, the temptress who lures Little Joe from Petunia’s side, and even Butterfly McQueen and Louis Armstrong show up, though the latter’s trumpet solo was cut, sadly. Dramatically staged — it builds to a tornado climax somewhere between “A Matter Of Life And Death” and “The Wizard Of Oz” — it’s remarkable for how sincerely it addresses the idea of faith and redemption, even if there is a sense that the afterlife is important mainly as an escape from the narrowly proscribed life of a 1940s African-American.
Best Number: All of Waters’ numbers — some torch songs, some spirituals — are dynamite, but the devil’s got the best tunes, so we’ll go with Horne’s rendition of “Honey In The Honeycomb,” the most suggestive lyric until Kelis‘ “Milkshake” came along.
24. “On The Town” (1949)
Recently and brilliantly nodded to in the Coen Brothers’ “Hail, Caesar!,” “On The Town” shouldn’t really work. It has the wispiest of plots (three sailors go on shore leave — the wholesome kind, not the STD kind), throws out much of the Leonard Bernstein score that made it a hit on Broadway, and doesn’t really deliver a classic song that’s endured outside of the film (“New York, New York” comes closest, but is sort of overshadowed by its namesake these days). And yet Gene Kelly and Stanley Donen’s film is still an absolute joy, a Technicolor love letter to NYC that delivers astonishing set piece after set piece, with some of the greatest choreography ever seen in an Hollywood movie (plus arguably Frank Sinatra at his hottest ever, which is quite a feat).
Best Number: It’s not the best choreographed, but “New York, New York” is the most iconic.
23. “Calamity Jane” (1953)
It’s hard to credit now that “Calamity Jane” was summoned into being to cash in on the runaway success of “Annie Get Your Gun” — for various reasons, Doris Day chief among them, it has grown in stature since and arguably now eclipses the Betty Hutton vehicle (depending on who you ask; I know passions run high on this one). Which is not to say it’s all-out greatness — it’s poorly paced and overproduced to a rootin’, tootin’ degree. But you really can’t take it away from Day, who tears into every scene with the sparkling, ineffably cheerful energy that she’s famous for, and if her scrubbed-clean image is a little too antiseptic for you, you can take comfort in interpreting the film as a lesbian love story, ignoring the Confederate flag-waving and imagining just how cool it would be if it played in reverse, with Calam abandoning pretty frocks and domesticity for chaps and six-shooter.
Best Number: “Just Blew In From The Windy City” has some choice lyrics and features Day showcasing a less well-known talent for dance, pratfalling and acrobatics.
22. “Grease” (1978)
It’s not as elegant or sophisticated as most of the very best movie musicals, but “Grease” is undeniably one of the most enduringly popular and populist, and with good reason. Every one of Warren Casey and Jim Jacobs’ song feels like a chart-topper (well, maybe not “Look At Me, I’m Sandra Dee”), and while director Randal Kleiser isn’t exactly Busby Berkeley, he conjures up a bright, sunny version of 1950s teen-hood that remains ageless, even if most of the cast are visibly in their 30s. And you only have to watch the (decent enough) recent live TV version to realize the magic that John Travolta, Stockard Channing and, we guess, Olivia Newton-John brought to the party. You can look down your nose at it, but there’s a reason you probably know three-quarters of the songs by heart.
Best Number: We nearly went for “Greased Lightning,” but it’s hard to think of a more joyous musical finale than karaoke fave “You’re The One That I Want.”
21. “Willy Wonka & The Chocolate Factory” (1971)
Perhaps because it’s so successful as so many other things — family film, comedy, fantasy, rediscovered cult classic, Roald Dahl adaptation and Gene Wilder vehicle — it’s easy to forget that Mel Stuart‘s 1971 film is also a musical, with some pretty ace tunes to prove it. Managing the balancing act between light and dark much better than almost all the other adaptations of the notoriously dark-hued children’s author’s work (though Dahl himself reportedly loathed the changes made to his screenplay by uncredited co-writer David Seltzer), it’s the rare kids film that doesn’t just bear up on rewatching, but actually sort of improves, though if you revisit it as an adult, you may find that all the bits you remember making you happiest now just make you cry. Or is that just me?
Best Number: The sweet strains of signature tune “Land Of Pure Imagination” are undercut with something, if not sinister, then certainly ambivalent by Wilder’s mysterious, mischievous, melancholic performance of it.
