Dive into Oscars history and you’ll quickly discover every category has a complicated, often strange history. Trace a category’s history and you can watch trends come and go — from different acting styles to changing tastes in cinematography — as movie history moves forward.
Some prizes, however, have taken more twists and turns with the times than others. The Best Original Song category, for instance, has produced some immortal winners (“When You Wish Upon a Star,” “Over the Rainbow,” “Mona Lisa,” “It’s Hard Out Here for a Pimp”) but also some baffling, sometimes awful, choices. At certain points in its history, it’s reflected popular taste. At others, it’s felt woefully behind the times. And there’s no predictable pattern to the swings, either: “Theme from Shaft” can win one year and the funkless “The Morning After” take the prize the next. Some years the Academy has an overabundance of choices, others it can’t even find five nominees and gives nods to one song from The Muppets, another from Rio and calls it a day.
One thing’s for sure, though: You can put together a pretty great playlist just from the losers. What follows is an attempt to do just that, one that will hopefully put some great songs on your radar while doubling as a short history of how the category has changed over time.
Track 1: “That Thing You Do!” from That Thing You Do! (1996)
How good is this song from Tom Hanks’ directorial debut? So good it never sounds tiresome any of the approximately 700 times the fictional band The Wonders (or Oneders) performs it over the course of the film. Written by Adam Schlesinger — then best known as a member of Fountains of Wayne, later to become a sought-after songwriter for film, theater and television — it captures the infectious spirit of the mid-1960s moment when seemingly every American kid with a guitar set out to be The Beatles, and some got closer than they ever dreamed.
Schlesinger’s garage band throwback sounded fresher than his competition, and the song offered a poppy bright spot in a year dominated by a bunch of wallpaper-like adult contemporary-friendly nominees. The Academy didn’t bite, which might be an appropriate fate for a song about musical also-rans. It would kick off any playlist with a bang, though, which makes it the perfect starting point for this tour of vital losers.
That Year’s Actual Winner: “You Must Love Me,” from Evita
Track 2: “Town Without Pity” from Town Without Pity (1961)
Dimitri Tiomkin would be one of the most successful composers in film history even if he never made it onto the hit parade. But one of the Tiomkin’s most lasting contributions guaranteed his music would reach even listeners who never saw the films in which they appeared (and might lure some curious listeners to the theater in the process). Tiomkin picked up the habit of writing both a film’s score and its theme song — often weaving the latter into the former — with High Noon. That film’s “The Ballad of High Noon (Do Not Forsake Me, Oh My Darlin’)” became a hit in 1952, helping to drum up interest in the film, winning an Oscar in the process. Nine years later, “Town Without Pity” didn’t, but it did help launch Gene Pitney’s career by conjuring up a proto-Springsteenian vision of a no-good place that crushes those who stay too long.
That Year’s Actual Winner: “Moon River” from Breakfast at Tiffany’s
Track 3: “Save Me” from Magnolia (1999)
That “Town Without Pity” competed against the great “Moon River” might help explain its loss, but maybe the Academy just doesn’t appreciate stunningly concise musical depictions of despair? Exhibit B: Paul Thomas Anderson built his third film — a sprawling depiction of an L.A. filled with troubled, lonely souls — around the music of Aimee Mann, drawing on songs from her then-unreleased album Bachelor No. 2 and giving a central spot to this song written for the film. “Save Me” had tough competition from other 1999 offerings, which included South Park: Bigger, Longer, and Uncut’s “Blame Canada” and Toy Story 2’s “When She Loved Me.” All of them lost, however, to a track written by Phil Collins for Tarzan.
That Year’s Actual Winner: “You’ll Be In My Heart,” from Tarzan
Track 4: “Against All Odds (Take A Look at Me Now)” from Against All Odds (1984)
Not that there’s anything wrong with Phil Collins. In choosing the nominees from 1984, the Academy had no shortage of hits from which to choose, thanks in part to corporate synergy that turned movie theme songs into Top 40 hits, whose music videos doubled as movie ads in an endless cycle of self-promotion. (Tiomkin, who died in 1979, would undoubtedly have approved.) The nominees included two hit songs from Footloose (“Maniac” and “Let’s Hear it For the Boy”), one from The Woman in Red (Stevie Wonder’s “I Just Called to Say I Love You”) and “Ghostbusters,” from, you guessed it, Ghostbusters. Collins’ power ballad from the largely forgotten thriller Against All Odds turned haunted yearning and a big drum sound into a summer-long hit. Collins was not, however, invited to perform the song at the Oscars, which opted for a bafflingly awkward rendition by singer/dancer Ann Reinking instead.
That Year’s Actual Winner: “I Just Called to Say I Love You,” from The Woman in Red
Track 5: “The Look of Love” from Casino Royale (1967)
The Oscars took a long time to nominate any songs from James Bond movies, in spite of those films putting their themes front and center over the credits, just waiting to be nominated. It would take until 1973’s “Live and Let Die” for a proper Bond theme to get a nod, no doubt helped along by the presence of Paul McCartney. By then, the Academy had already ignored “Goldfinger” and in 1967 looked past Nancy Sinatra’s terrific “You Only Live Twice” theme, to nominate Burt Bacharach and Hal David’s “The Look of Love” from the off-brand Bond goof Casino Royale. Fortunately the song’s the best part of a largely embarrassing movie, understandably becoming a big hit for Dusty Springfield. Unfortunately, it lost the Oscar to Rex Harrison singing to animals. (The Oscars did, however, help make it a hit a second time by inviting Sergio Mendes and Brasil ’66 to perform at the ceremony, sending that group’s cover up the charts.)
That Year’s Actual Winner: “Talk to the Animals” from Dr. Dolittle
Track 6: “Miss Misery” from Good Will Hunting (1997)
The 1998 Oscars ceremony produced no odder sight than singer/songwriter Elliott Smith flanked by Trisha Yearwood and Celine Dion after each performed their nominated songs. Yearwood and Dion were hitmakers: Smith was little known outside of indie circles until contributing “Miss Misery” to the soundtrack of Good Will Hunting. The spare song sounded as out-of-place as Smith looked that night, but its rawness resonated even when accompanied by the orchestra’s strings.
That Year’s Actual Winner: “My Heart Will Go On,” from Titanic
Track 7: “Mystery of Love” from Call Me By Your Name (2017)
Smith helped influence a whole generation of songwriters specializing in delicately crafted, emotionally vulnerable songs, Sufjan Stevens among them. This quiet, heartbreaking track from Call Me By Your Name, one of two Stevens’ songs on the soundtrack, never had a shot at winning, but it probably helped expand some viewers’ tastes when it played to the biggest audience of Stevens’ career.
That Year’s Actual Winner: “Remember Me,” from Coco
Track 8: “Cheek to Cheek” from Top Hat (1935)
Here’s the thing about the Best Original Song Oscar: It now regularly spotlights good, often great songs. But it’s no longer the premier showcase for the best American songwriting has to offer, the sort that turns away future classics because it chooses to reward other future classics. At the height of the American movie musicals, films became the place to make a song immortal. For proof, look no further than 1935, when eventual winner “Lullaby of Broadway” competed with Jerome Kern’s “Lovely to Look At” and Irving Berlin’s “Cheek to Cheek.” The latter definitely helps lift the mood after Smith and Stevens, so it’s strong fodder for the eighth slot.
That Year’s Actual Winner: “Lullaby of Broadway” from Gold Diggers of 1935
Track 9: “Pennies From Heaven” from Pennies from Heaven (1936)
Another year, another bunch of American songbook standards competing with one another at the Oscars. That any song beat out “Pennies from Heaven” or “I’ve Got You Under My Skin” seems unthinkable, but with “The Way You Look Tonight” in the mix, it kind of makes sense. For the purposes of this playlist, let’s go with Bing Crosby singing “Pennies From Heaven” to pick up the tempo a bit.
That Year’s Actual Winner: “The Way You Look Tonight,” from Swing Time
Track 10: “I Fall in Love Too Easily” from Anchors Aweigh (1945)
In 1946, the Academy capped the number of Best Original Song nominees at five, perhaps sensing the competition had gotten out of control. In 1945, however, it nominated an astounding 14 songs. There’s no shame in losing to Rodgers and Hammerstein, but Jules Styne and Sammy Cahn’s “I Fall in Love Too Easily,” as sung in the film by Frank Sinatra, could just as easily have taken the prize.
That Year’s Actual Winner: “It Might As Well Be Spring” from State Fair
Track 11: “My Kind of Town” from Robin and the 7 Hoods (1964)
Speaking of Sinatra, the quintessential Jersey kid scored a hit singing about the Windy City thanks to this Rat Pack comedy set in the Chicago underworld. The paean to all things Chicago, written by Sammy Cahn and Jimmy Van Heusen, took on a life of its own, helping Sinatra make the charts even as the Beatlemania swept the nation.
That Year’s Actual Winner: “Chim Chim Cher-ee” from Mary Poppins
Track 12: “Ave Satani” from The Omen (1976)
Like a good Oscars ceremony, a good playlist needs some curveballs to keep from growing boring. The perfect soundtrack for a black mass, Jerry Goldsmith’s score for The Omen won an Oscar in 1977, the only Academy Award the great composer would receive. Surprisingly, one track from that soundtrack also picked up a Best Original Song nomination. Even Satan never had a chance against Barbara Streisand’s “Evergreen,” but “Ave Satani” remains one of the Oscars’ least expected Best Original Song nominations, and certainly the scariest.
That Year’s Actual Winner: “Evergreen,” from A Star is Born
Track 13: “I’ve Seen it All” from Dancer in the Dark (2000)
Next, we move on from the scariest song to one of the saddest. Though she found working with Lars Von Trier so unpleasant she essentially swore off movies after making Dancer in the Dark, Björk delivers a heartbreaking performance as Selma, a factory worker trying to save her son from going blind as she loses her own sight. “I’ve Seen it All” gives the film its emotional core as Selma bids farewell to sight itself. That Björk attended the Oscars in a dress shaped like a swan has overshadowed her moving performance that night, particularly for those who never made the connection between her tragic character and the origin of the term “swan song.”
That Year’s Actual Winner: “Things Have Changed,” from Wonder Boys
Track 14: “Everything is AWESOME” from The LEGO Movie (2014)
Allow me to lift the mood again with a song that blurs the line between happiness and mania. That’s by design, making the track — performed by Tegan & Sara and Lonely Island — the perfect fit for the cheerfully dystopian world seen in the opening of The LEGO Movie, a place where awesomeness is not optional. (Or, as the song puts it, “It’s awesome to win! It’s awesome to lose!”) It’s so upbeat it’s creepy, but just try getting this earworm out of your head.
That Year’s Actual Winner: “Glory,” from Selma
Track 15: “All the Stars” from Black Panther (2018)
Kendrick Lamar curated a killer soundtrack that could easily stand on its own for Ryan Coogler’s 2018 Marvel movie Black Panther. The standout tracks include “All the Stars,” a collaboration between Lamar and SZA that preceded the film’s release and doubled as promotion for the film to come. (Again, things really haven’t changed that much since Dimitri Tiomkin’s days.)
That Year’s Actual Winner: “Shallow,” from A Star is Born
Track 16: “Alfie” from Alfie (1966)
It’s only appropriate to close on a pensive track that doubles as a reminder of how a great song can elevate a so-so movie. 1966’s Alfie gave Michael Caine one of his signature roles as a London playboy, but its Swinging London spirit quickly sours into a moralistic drag of a movie that devolves into thinly veiled sermonizing by the end. The theme, however, finds a more elegant way to express a sense that high times and casual attachments may not offer much satisfaction in the end. Essentially, the song, written by Bacharach and David and first sung by English singer Cilla Black, beautifully conveys what the movie struggles to say.
That Year’s Actual Winner: “Born Free” from Born Free