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The 10 Best (and Worst) Best Song Oscar-Winners of All Time

From ‘Over the Rainbow’ to ‘It’s Hard Out There for a Pimp,’ the Best Song category’s cream of the crop – and bottom of the barrel

The magic of the movies depends on sound as much as sight, and ever since the Academy of Motion Pictures and Sciences established the Best Song category for the seventh annual Academy Awards in 1933, the Oscars have honored the finest show tunes, pop tunes and rock-to-rap bangers ever to grace the screen. Or at least, they’ve tried to. As with any other category, the gold has gone to stone classics and stinkers alike; more often than not, the winners tell us as much (or more) about the values of the era as the value of the songs themselves. 

We’ve already delved into the 20 greatest Best Song performances at the Oscars, paying lip service to nominees ranging from “Endless Love” to “Everything Is Awesome!” But what about the songs themselves? Which of the winners rank head and shoulders above the rest? And which ones feel like a painful punch in the gut every time you hear them? For your listening pleasure (half the time, anyway), we’ve cued up the 10 best and the 10 worst Best Song winners of all time. Are they all worth listening to if you want to understand the Oscars? As one winner put it, you’re daaaaaaamn right.

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Worst: “Born Free” (‘Born Free,’ 1966)

Written by blacklisted screenwriter Lester Cole under a pseudonym and focusing on the true story of an adopted lion cub’s return to the wild, Born Free‘s a perfectly admirable movie. But its theme song, penned by James Bond theme-song composer John Barry and his frequent collaborator Don Black, is a perfectly abominable song – a corny AM-radio singalong released in one of the most astonishing years for popular music ever.

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Best: “Over the Rainbow” (‘The Wizard of Oz,’ 1939)

For its first decade or so, the Best Song Oscar had a damn good ear for future standards of the American songbook: “The Way You Look Tonight,” “Thanks for the Memory,” “When You Wish Upon a Star,” “Swinging on a Star” … they all racked up wins. Yet none of them touch the devastatingly dreamy centerpiece of the Golden Age masterpiece The Wizard of Oz. Written by Harold Arlen and Yip Harburg and performed with inimitable intensity by the iconic Judy Garland, the song and its singer would become cornerstones of queer culture – and anyone wishing for a better world than this.

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Worst: “You Light Up My Life” (‘You Light Up My Life,’ 1977)

And now, the answer to the musical question, Can a song sound beige? Arguably the nadir of Seventies soft rock, “You Light Up My Life” became a smash hit for Debby Boone, daughter of rock and roll whitewasher Pat, topping the charts for a record-setting 10 weeks. Her version has been spun as an inspirational Christian hymn, but the story behind the song is as ugly as it gets. Songwriter Joe Brooks effectively swiped it from its original singer, Kasey Cisyk, allegedly after she spurned his sexual advances, instructing Boone to imitate Cisyk’s vocals instead. Brooks himself committed suicide in 2011 while awaiting trial for dozens of rape and sexual assault charges. 

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Best: “Raindrops Keep Fallin’ on My Head” (‘Butch Cassidy and the Sundance Kid,’ 1969)

It was written by the great songwriting duo Burt Bacharach and Hal David for a movie starring the incomparable acting duo Paul Newman and Robert Redford about the great train-robbing duo of the title. And not surprisingly, the insanely catchy “Raindrops” was a smash hit for singer B.J. Thomas, whose raspy post-laryngitis vocals gave the carefree lyrics a lived-in feel. It’s also a triumph for Bacharach, whose famously twisty chord progressions suit the song perfectly – a leisurely sonic stroll with no particular place to go.

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Worst: “The Way We Were” (‘The Way We Were,’ 1973)

“Misty water-colored mem’ries” … of McCarthyism? That seems to be the implication of Barbra Streisand’s theme song for her period-piece romance with Robert Redford, who plays a writer whose Hollywood career is threatened by his relationship with Streisand’s Marxist activist during the Red Scare. Their love affair is as awkward a match as the film’s mix of heavy politics and rote melodrama; the track fits the latter to a tee, and that’s not a compliment. Written by Marvin Hamlisch and Alan and Marilyn Bergman, this siiiigh in musical form became Babs’ signature song, dulling our own mem’ries of the livewire musical-comedy chops that made her a star in the first place.

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Best: “Lullaby of Broadway” (‘Gold Diggers of 1935,’ 1935)

The greatest romance in movie history may well be between America’s two great entertainment meccas: Hollywood and New York. Seen in that light, “Lullaby of Broadway” is the love letter to beat. Written by the songwriting team of Al Dubin and Harry Warren for an entry in the lucrative Gold Diggers musical franchise – this one directed by legendary choreographer Busby Berkeley – it glorifies the glamour of the wild nightlife surrounding the Great White Way. Broadway returned the favor decades later, making it a centerpiece of the blockbuster Dubin/Warren jukebox musical 42nd Street.

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Worst: “Love Is a Many-Splendored Thing” (‘Love Is a Many-Splendored Thing,’ 1955)

The most interesting thing about the schmaltzy title track for the melodrama of the same name is that lyricist Paul Francis Webster is also responsible for both the slow-burn heartache of Duke Ellington’s “I Got It Bad (and That Ain’t Good)” and the friendly neighborhood superheroics of the original animated Spider-Man theme song. The least interesting thing about it is, well, everything else. Composer Sammy Fain’s syrupy melody is emblematic of the easy listening the Academy has a long history of rewarding.

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Best: “White Christmas” (‘Holiday Inn,’ 1942)

Speaking of standards, three quarters of a century have failed to topple Irving Berlin and Bing Crosby’s holiday classic as the king of Christmas songs. (A queen, however, eventually came along.) Like “Over the Rainbow,” it’s a song about dreaming of happiness you might never have, which is why decades of December ubiquity haven’t dimmed its melancholy brightness.

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Worst: “In the Cool, Cool, Cool of the Evening” (‘Here Comes the Groom,’ 1951)

The music is by Hoagy Carmichael, whose 1927 song “Stardust” has haunted the reverie of everyone from Willie Nelson to Martin Scorsese (who put it in both Goodfellas and Casino). The lyrics are by Johnny Mercer, an Oscar favorite with four wins (including “Moon River”) and 19 nominations. The vocals are by Jane Wyman, who had the good sense to dump Ronald Reagan, and Bing Crosby, who’s freaking Bing Crosby. Yet the result is an irritatingly upbeat dud with a jingly-jangly melody and gibberish lyrics. That’s showbiz for ya.

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Best: “Take My Breath Away” (‘Top Gun,’ 1986)

Track for track, the 1980s were Oscar’s best decade for bestowing Best Song on pop classics. “Fame,” “Arthur’s Theme (Best That You Can Do),” “Up Where We Belong,” “Flashdance … What a Feeling,” “I Just Called to Say I Love You,” “Say You, Say Me,” “(I’ve Had) The Time of My Life,” “Let the River Run” — that’s as stacked a lineup as the category came up with since its earliest years. But Berlin’s “Take My Breath Away” is, arguably, the best of the bunch. Written by EDM godfather Giorgio Moroder with lyrics by his frequent soundtrack collaborator Tom Whitlock (they met when Whitlock, a struggling musician, fixed Moroder’s Ferrari), its massive, nearly percussive synth melody is a signature sound of the era. Moroder himself considers it his crowning achievement, which is saying something.

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Worst: “Can You Feel the Love Tonight” (‘The Lion King,’ 1994)

It didn’t have to be this way. When Disney’s big animated comeback The Little Mermaid upended the Eighties’ string of Top 40 Best Song winners in 1989, it did so not with a ballad (although “Part of Your World” is one of the studio’s best) but with the calypso jam “Under the Sea.” Beginning with 1991’s Oscar for “Beauty and the Beast,” though, the category became a cartoon-ballad free-for-all, with live-action winners mostly following suit. The result is one of the dreariest, schmaltziest runs in the award’s history, and they don’t come much goopier than Elton John and Tim Rice’s love song for lions. Pro tip: “Funeral for a Friend/Love Lies Bleeding” is twice as long but about 40 times as awesome.

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Best: “It’s Hard Out Here for a Pimp” (‘Hustle & Flow,’ 2005)

Sure, go ahead and goof on how Three 6 Mafia’s triumph gifted us with the unlikely but true phrase “the Academy Award–winning composers of ‘Slob on My Knob.'” But “It’s Hard Out Here for a Pimp” – co-written by DJ Paul, Juicy J, and Frayser Boy, and performed in the film by future Empire headliners Taraji P. Henson and Terrence Howard — is so much more than the novelty element. (Or Three 6’s infectious excitement after winning.) This song enabled the single most uncompromisingly underground act ever to take the Oscar stage to win the film industry’s top honor – bringing long-overdue recognition to Black hip-hop artists in general and the Dirty South in particular.

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Worst: “My Heart Will Go On” (‘Titanic,’ 1997)

Celine Dion is funny, good-hearted, and can sing the shit out of Jim Steinman as well as anyone this side of Meat Loaf. Even Elliot Smith liked her. And chances are that by now, you’ve heard her berserkly popular theme from James Cameron’s billion-dollar baby Titanic enough times to have grown kind of fond of it, like a weird relative you only see at Thanksgiving. But a song shouldn’t have to bludgeon you into submission, and that’s exactly what the melody by well-regarded film composer James Horner, lyrics by Will Jennings and those larger-than life vocals by Dion do. We do love the performance she gave at the ceremony. But if we never hear this again, our hearts will most certainly still go on.

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Best: “Let It Go” (‘Frozen,’ 2013)

This Disney fable is the highest-grossing animated film of all time, and it has three little words to thank for it. Written by the wife-and-husband team of Kristen Anderson-Lopez and Robert Lopez, the song’s message of self-acceptance and empowerment resonated strongly with co-director/screenwriter Jennifer Lee; she and her team ended up reimagining the whole movie around it, changing “snow queen” Elsa from a villain to a sympathetic co-protagonist. The result is a showstopping showcase for the talents of both singer Idina Menzel and the animating team, unleashing Elsa’s powers like something between a superhero origin story and a Pride parade. One of the best songs in Disney’s decades-long repertoire, it imprinted itself on the consciousness of a generation faster than you can say “The cold never bothered me anyway.”

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Worst: “You’ll Be in My Heart” (‘Tarzan,’ 1999)

Think of the drum hit from “In the Air Tonight.” Now imagine its exact aural and emotional opposite. Congratulations: You’ve just won the Best Song Academy Award! Phil Collins collected the statue for the lamest entry in a very lame run of animated-feature Oscar winners, which in addition to Elton’s Lion King contribution also included Aladdin‘s wedding-song staple “A Whole New World,” Pocahontas‘s would-be woke anthem “Colors of the Wind” and the Whitney/Mariah duet “When You Believe” from Dreamworks’ Prince of Egypt. Weirdly, Collins’ songs for the soundtrack were inserted as-is rather than sung by the characters, because co-director Kevin Lima thought a singing Tarzan “would be ridiculous.” As opposed to the normal, non-ridiculous Tarzan?

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Best: “Into the West” (‘The Lord of the Rings: The Return of the King,’ 2003)

Think of this as the Sméagol to the Gollum of “My Heart Will Go On.” Like that titanic track, “Into the West” is the climactic power ballad of a three-hour-plus, billion-dollar-grossing epic, created as a collaboration by a respected film composer and an established pop star with serious vocal chops. But where “Heart” steamrolls, “West” soars and soothes. Co-written Fran Walsh (co-screenwriter of the Rings films), composer Howard Shore and Eurythmics alumna Annie Lennox, it builds to its bittersweet high notes with true Tolkien-ian splendor. 

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Worst: “We May Never Love Like This Again” (‘The Towering Inferno,’ 1974)

Today, we think of Seventies Hollywood as the stomping ground of maverick masters like Scorsese and Coppola, and the birth of the blockbuster era midwifed by their pals Spielberg and Lucas. Yet the decade was dominated by big-budget, star-studded disaster movies that were every bit as popular and ubiquitous as superhero movies are today. And two of the genre’s biggest box-office successes took home Best Song Oscars: “The Morning After” from The Poseidon Adventure, in 1972 – and this virtually identical track from The Towering Inferno two years later. Both are collaborations between singer Maureen McGovern and songwriters Al Kasha and Joel Hirschhorn. And while it was tough to pick which one was more offensive to human ears, let’s just say “We May Never Love Like This Again” won for a reason. We may never hear anything the same ever again.

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