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The 20 Best Original Song Oscar Winners of All Time

Chris Willman
·17-min read

With the Oscars coronating another winner for best original song, it’s an occasion to look back at 20 of the times when the golden guy got it most right with the tune he carried, from “Lullaby of Broadway” to “Lose Yourself.”

1: “White Christmas”
from “Holiday Inn” (1942), by Irving Berlin

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It always feels strange watching the “Holiday Inn” scene where Bing Crosby, playing a songwriter, teaches this song to Marjorie Reynolds as something that had recently come off the top of his head, because implicit in the scene is the idea that “White Christmas” was written by a human, not God. The same could be said of its status of an Oscar winner, which never fails to surprise younger generations: Isn’t it from a hymnal of some sort? If it’s true that Berlin said at the time that it wasn’t just the best song he ever wrote but “the best song anybody ever wrote,” he wasn’t far off. Ostensibly about being in Beverly Hills waxing wistful for a great white north, it really could be about any longing that still has the potential to be fulfilled again. Or maybe it really is just about the beauty of precipitation after all. Because sometimes a snowman holding a cigar is just a snowman holding a cigar.

2. “Over the Rainbow”
from “The Wizard of Oz” (1939), by Harold Arlen and Yip Harburg

When you think about it, both of these two top-tier Oscar songs are ditties about the weather. But only one of them helped inspire a flag. (Which is fine; no one really needs a white flag in the world.) As “I wish” songs go, it’s a little more fatalistic than “White Christmas”; Dorothy’s chances of escape and having her wildest dreams come true sound a little more distant than Crosby being able to just hop on a plane to Minnesota if he really felt that strongly. Part of what’s great about the song — and what allegedly scared some studio execs that were ready to toss it — is how completely dead it stops the movie before it’s even gotten started, so that Judy Garland can sing her quest song before there’s any literal quest to speak of. Watching the rough cut, it might have seemed like an avoidable stall. But in essence, “Over the Rainbow” is the movie, tornados and tin men notwithstanding. And it’s life… or our thwarted, still faintly possible vision for it.

3. “When You Wish Upon a Star”
from “Pinocchio” (1940), by Leigh Harline and Ned Washington

The great triumvirate of movie “wish” songs is completed by Jiminy Cricket’s opening and closing anthem about wishing to be real… something we could all aspire to. It’s difficult to hear this song afresh, especially after its instrumental got adopted as a theme park siren song and the logo music for every Disney film since the 1980s. That ubiquity has made most of us inured to its charm. The song is a complete lie, of course; it’s the secular version of the prosperity gospel, where success is assured if we just pray hard enough. Yet the song’s democratization of wish fulfillment still has the power to feel touching; “makes no difference who you are… no request is too extreme…” It’s the burgeoning Disney corporation as Christ stand-in, telling Depression-weaned kids that every life matters. And isn’t the simple three-word phrase “fate is kind” one of the most audacious song lyrics ever? For every real girl and real boy in need of some blind hope as well as a conscience, this song remains a real joy.

4. “Theme From ‘Shaft’”
from “Shaft” (1971), by Isaac Hayes

And now, a different kind of wish fulfillment: that you could be a “private dick that’s a sex machine to all the chicks.” It’s impossible not to hear this song’s wah-wah guitar and 16th-note hi-hat beat and not instantly acquire some swagger. Although we haven’t tested this theory out and hope not to for a while, you could probably hear this on your deathbed and still pick up a little bit of swagger as the consciousness is ebbing out of your body. It almost feels wrong to think of this as a song, as opposed to a tremendous piece of score that happens to have some words attached; Hayes’ lyrics practically serve as percussive afterthoughts to music that has already let us know that everything is not just all right but damn right. It’s the power of Hayes’ expert orchestral funk that an opening montage set in New York City at one of its lowest points makes that seem like a fairyland we wish we could revisit as much as any Oz.

5. “All the Way”
from “The Joker Is Wild” (1957), by Jimmy Van Heusen and Sammy Cahn

This is one of those Great American Songbook standards that almost no one realizes or remembers is from a movie. That’s partly because, as Frank Sinatra introduces it in a late ‘50s gangster drama, the framing isn’t designed to spotlight the honest emotion of the song he’s performing on stage as much as the glances being exchanged between shady figures in the audience. Nonetheless, it utterly transcends the context within which it was introduced into the world. It’s a brilliant ballad about being uncompromising in romance — about how being only half-loved isn’t good enough. The song is presented as a vow of all-consuming ardor from a strong suitor, but it really feels like it was penned as a reminder or anthem of aspiration for anyone who’s gotten too used to settling for less.

6. “The Windmills of Your Mind”
from “The Thomas Crown Affair” (1968), by Michel Legrand and Alan and Marilyn Bergman

In the simplest sense, it’s a song about ADHD. In the late ‘60s, a number about having too much going on in one’s head could also be described as “trippy,” a word not always associated with the usually grounded canon of Alan and Marilyn Bergman. Married to the long wind-up of a melody from Legrand, anyway, these thoughts added up to a wistful-sounding magnificence. What did any of it have to do with jewel heists? Or Steve McQueen doing aerial donuts in the movie’s glider interlude? Not entirely sure of that. What we can be certain of is that this is one of those songs, like “All the Way,” that improved and took on new life outside of their original cinematic context. Noel Harrison’s rushed delivery on the soundtrack was no match for the resonance the song took on when Dusty Springfield took it over and slowed it down to a more haunting pace. But in any rendition, it’s clear what a one-of-a-kind “Windmills of Your Mind” is – a song that takes its good time in circling back in on itself, as it describes a dreamy, stream-of-consciousness state in a coherent enough way that sent even the squarest Academy members of 1968 reaching for the ballot box.

7. “Lullaby of Broadway”
from “Gold Diggers of 1935” (1935), by Harry Warren and Al Dubin

Like “Windmills of Your Mind,” “Lullaby of Broadway” describes a state of not being able to go to sleep — not from an overactive brain, but because there’s too much partying to be done. Other songs have been written alluding to New York as the city that never sleeps. None of them have bested this ‘30s banger about staying up to see the dawn and sleeping till it’s time to take up nightlife all over again.

8. “Things Have Changed”
from “Wonder Boys” (2000), by Bob Dylan

“I used to care, but things have changed” — at last, a song for the old at heart. Here’s the counterpoint to all those “I wish” songs the movies specialize in: Dylan has gone over the rainbow to the other side and found a puddle. But at least he’s going to be bemused about it, in his own grizzled way. (We might have thought of this at late-period Dylan at the time, but now that more than two decades have gone by, we realized that he was sounding this world-weary at a spry not-yet-60.) Whether it exactly suits the movie’s Michael Douglas character or not, sometimes what we all need is a good, old-fashioned de-enlightenment anthem.

9. “Let It Go”
from “Frozen” (2013), by Kristin Anderson-Lopez and Robert Lopez

Elsa, too, used to care — about what anybody else thought — and, yes, things have changed. For a song that ostensibly has 9-year-olds at the top of its target-demo list, “Let It Go” has a lot of unpacking to do. What’s to be left behind, as the Disney musical’s ice princess leaves her palace behind to head out into the wilderness? The weight of unhealthy expectations, maybe, but also the possibility of immediate human connection, at this midpoint in the movie’s action. It’s a more emotionally complex mindset than even admirers of the song typically give it credit for, but then, it’s easy just to be swept up in the bravado of Idina Menzel’s vocal, without really thinking about all that’s lost and gained in not being bothered by the cold.

10. “Last Dance”
from “Thank God It’s Friday” (1978), by Paul Jabara

Sometimes happy endings come at 2 a.m., give or take a couple hours, depending on your local ordinances and liquor licenses. “Thank God It’s Friday” was not a movie that had “Oscar bait” written all over it, but it had to exist as a vehicle for one of Donna Summer’s triumphs — a disco classic that reassures us that sometimes an evening really does save the best for last.

11. “Baby, It’s Cold Outside”
from “Neptune’s Daughter” (1949), by Frank Loesser

In the annals of pop duets, there are few or none cleverer. Just as a piece of songcraft, it’s bold in how it trusts the listener not to lose track of the gender-segregated rhyme schemes even as these two very willing lovers interrupt and dance around one another. As it moved on from its long-forgotten filmic context to become a December standard, the song became a flashpoint for debate over whether it celebrates coercion or a woman abandoning flimsy excuses on the way to owning her own desire. It’s really as sex-positive as 1940s songs got, especially for the female duet partner, who clearly has no intention of skipping out on one cigarette more.

12. “Evergreen”
from “A Star Is Born” (1976), by Barbra Streisand and Paul Williams

Are you an “Evergreen” man or a “Way We Were” woman? You can take your pick of which all-timer original Streisand movie anthem is your particular brand of butter. But a side-by-side taste test reveals that she topped herself, in this song that she wrote the melody for herself, albeit clearly with some help… by which we mean help from the divine. It’s a boldly constructed ballad that dispenses with easy verse/chorus format — but then, would it make sense for a song called “Evergreen” to go through a whole round of songwriting seasons? In the film, as she sings it to Kris Kristofferson, Streisand makes a funny face as she heads into the last few bars, like it’s challenging her. But nobody’s really laughing as she proceeds into one of pop’s most spine-tingling decrescendos.

13. “Lose Yourself”
from “8 Mile” (2002), by Eminem, Jeff Bass and Luis Resto

“Lose Yourself,” the first hip-hop song to win an Oscar (and still in rarefied company in that regard), stands as one of Eminem’s more pop-friendly efforts, but a big part of what makes the song work is the exquisite tension of how long he keeps the seemingly extemporaneous verses going before it loses itself in a chorus. The almost “Kashmir”-like guitar line ramps up the tension, as Eminem keeps going and going, almost erring on the side of recounting the film in progress… but you don’t really want the recap to end or the drama to stop escalating. As full of hubris as Eminem’s raps might usually be, this one founds power in a kind of humility and universality, fully articulating the pre-performance fear that choking might be a possibility — and the ironic concept that a loss of self-consciousness is the hurdle to get over in fully expressing yourself.

14. “Thanks for the Memory”
from “The Big Broadcast of 1938” (1938), by Ralph Rainger and Leo Robin

This song became infinitely better known as Bob Hope’s endlessly adaptable solo signature song, as opposed to the much more interesting movie duet it began life as. In the film, Hope and Shirley Ross are a divorced couple who have a re-meet-cute and share mostly sweet recollections over a drink. (A censor forced a slight change in a lyric recalling their honeymoon: “That weekend at Niagara when we hardly saw the Falls” became “barely saw the falls,” lest anyone be put in mind of non-stop newlywed sex.) The idea is that there are no hard feelings between these two, given their shared bank of sweet memories — they’re practically the original conscious uncouplers. The song has a sad ending, though, facing the reality that no divorce song can really be that whimsical… even if the ending the film itself is headed for is inevitably a happier one. The whole modern thing about “…it’s complicated”? The ‘30s had that down.

15. “Mona Lisa”
from “Captain Carey, U.S.A.” (1950), by Ray Evans and Jay Livingston

This song about (or at least inspired by) a painting is assuredly not like watching paint dry. Nat “King” Cole had the No. 1 hit with it not long after the movie’s release, but did not appear in the movie, a 1950 crime film set in Italy. “Captain Carey, U.S.A.” is a sort of film noir, but it would have taken an even more classic example of the form to be as worthy a vehicle as “Mona Lisa” really merited, as the song moved on and became a part of American popular culture in a way that movie didn’t. It’s easy to imagine the protagonist of a classic noir wondering what’s behind the beauty of a femme fatale as a singer warns: “Many dreams have been brought to your doorstep / They just lie there and they die there.” In any case, this ode to impenetrability is not the straight-up song of adoration its warm tone would suggest.

16. “It Goes Like It Goes”
from “Norma Rae” (1979), by David Shire and Norman Gimbel

In the modern era, a song about union formation would never be allowed to go out on a song as ambivalent as “It Goes Like It Goes,” a ballad that wavers between resignation and bare-bones hope and makes it sound like either would be just as beautiful. Before she was lifting us up where we belong, Jennifer Warnes was just the warbler to leave us with slightly less elevated lines like, “Maybe what’s good gets a little bit better, and maybe what’s bad gets gone.” You could almost think of this as one of the best Randy Newman movie songs that Randy Newman never wrote, at least when it’s opening with a lyric like “Ain’t no miracle bein’ born, people doin’ it everyday” and benefitting from his kind of bittersweet orchestration. That songsmith pros like Shire and Gimbel were able to pull off this idiosyncratic of a tune is a reminder of just what a different time the ‘70s were.

17. “The Way You Look Tonight”
from “Swing Time” (1936), by Jerome Kern and Dorothy Fields

“Swing Time” was sexy-time when Fred Astaire serenaded a getting-ready-to-go-out Ginger Rogers from another room (and was eventually joined by her). The movie hardly counts as forgotten, but the song is even more a part of modern popular culture, never far from the lips of any cabaret singer, or the heart of any true romantic with some institutional knowledge of the American songbook.

18. “Falling Slowly”
from “Once” (2007), by Glen Hansard and Marketa Irglova

Sometimes a great song is incidental to the film from which it sprang; in very rare instances, the movie would not exist, or certainly have endured, without a key number. That’s certainly the case with “Once” — not just in its movie form, but its subsequent Broadway incarnation — which seems to exist first and foremost as a vehicle for a song beautiful enough to have at least momentarily made the duo the Swell Season a household name. The real-life couple, who played busker strangers circling one another on the streets of Ireland, eventually slowly fell out. Their harmonies endured, colliding on a melody that seemed to celebrate their romance and portend its end all at once.

19. “I’m Easy”
from “Nashville” (1975), by Keith Carradine

Ironies abounded in this centerpiece number from Robert Altman’s “Nashville”: Carradine sings it in a club performance scene as a caddish singer/songwriter who seems to have written the acoustic ballad from the susceptible viewpoint of one of his victims… many of whom, real or prospective, are seated adoringly in his audience. It’s either a deeply vulnerable or deeply cynical anthem of open-heartedness. “Nashville” gets to play it both ways, really, but it’s a surprise the song hasn’t been covered more often for all the earnestness it might be worth.

20. “Streets of Philadelphia”
from “Philadelphia” (1993), by Bruce Springsteen

It’s not entirely clear whether Springsteen was trying to draw an exact analog between his lyrics and Tom Hanks’ AIDS-stricken character in the film, but the idea of “wasting away” fits whether you want to think of literal disease or just malaise as a state as sure as Pennsylvania. Springsteen cut multiple versions of the song, then went with the most minimalist one as the recording that became his last top 10 hit to date. At a 28-year-old time when general audiences were less likely to go see a film about a dying gay man than they would be in the 21st century, there was no doubt that Springsteen using his then-superpowers as a point of empathy was a factor in helping turn the film into a mainstream hit. It’s a renewable elegy for a tragic moment in American life that still bears hearing.

With these songs having been celebrated, you might reasonably ask: Hey, where are “Moon River,” “Can You Feel the Love Tonight,” “Flashdance… What a Feeling,” “The Way We Were,” “The Shadow of Your Smile,” “The Morning After,” “You’ll Never Know,” “Que, Sera Sera,” “Beauty and the Beast,” “A Whole New World,” “Under the Sea,” “Call Me Irresponsible,” “For All We Know,” “Chim-Chim Cheree,” “Zip-a-Dee Doo-Dah,” “Fame,” “Never on Sunday” and “Raindrops Keep Fallin’ on My Head” on this list? The answer: You are right — these are all also great songs, and possibly egregious oversights, and will surely be included in later revisions.

Meanwhile, you might also be wondering: How in the world could you overlook “Goldfinger,” “Have Yourself a Merry Little Christmas,” “Mrs. Robinson,” “Stayin’ Alive,” “New York, New York,” “Pure Imagination,” “Purple Rain,” “Can’t Help Falling in Love,” “Knockin’ on Heaven’s Door,” “A Hard Day’s Night,” “Help!,” “The Rose,” “To Sir With Love,” “Fight the Power,” “Happy,” “Once Upon a Dream,” “Diamonds Are Forever,” “Cruella de Vil,” “You Only Live Twice,” “Whistle While You Work,” “Always Look on the Bright Side of Life,” “Spoonful of Sugar,” “Feed the Birds,” “Call Me,” “Part of Your World,” “Someday My Prince Will Come” and “Big Bottom”? In this case, the overlooking can’t be counted as ours: None of these songs were even nominated for best original song, much less came up a winner.

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