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What’s The Worst Best Original Song In Oscar History?

The Academy Awards strive to highlight the most significant annual achievements in acting, the craft of making movies and, for some reason, which song from the last year was pretty good. Yes, the Oscar for best original song is a chance to look back on the small batch of tunes explicitly written for the medium of film. But that’s the problem; it’s a relatively small batch compared with the almost endless number of movies and actors the academy can choose from. It’s not a recipe for consistent excellence.

There are a few kinds of songs that show up repeatedly over the years. You’ve got the mediocre song added to the film adaptation of a beloved stage musical;1 one of the Disney, Pixar or Bond songs; or the song that wins but isn’t even the best tune from that movie.2 There are many years when the obviously superior song — “I Don’t Want to Miss a Thing,” “The Power of Love,” “Eye of the Tiger” or “The Bare Necessities” — loses. My favorite nominees of all are the C to C-minus ballads from extremely popular musicians grasping their best chance to win Oscar gold, such as Bono,3 Paul McCartney,4 Bruce Springsteen,5 Jon Bon Jovi,6 Justin Timberlake7 or, most of all, Sting.8

In other words, I find the best original song category fascinating because its nominees span such a wide range in quality — the most timeless songs in cinema history and songs that prove the music branch will nominate a ham sandwich if Bono or Randy Newman was involved in making it.

So let’s find out the worst best original song. (OK, we’ll find the best one too.) We took a 30-second clip from every best original song winner in Academy Award history and loaded the samples into a random matchup generator. Then we asked people to select which song they preferred. We promoted this across FiveThirtyEight’s social channels over several weeks. It’s not a scientific sample, but with more than 50,000 individual matchups evaluated, I’m confident that this ranking approximates prevailing attitudes toward the winners.9 We can then rank each song by the percent of matchups it won.

I was originally worried that the biases of the audience would penalize older songs over more recent songs, but that wasn’t the case; more to the point, it appears that we’re in a bit of a dark age when it comes to movie songs.

The best era for movie songs appears to be the 1980s and 1990s — bracketed by “Fame” in 1980 and “My Heart Will Go On” in 1997. The best 10 consecutive years of best original songs ran from 1986 through 1995, with Disney Renaissance hits combining with bangers like “Take My Breath Away” from “Top Gun” and “Time of My Life” from “Dirty Dancing” to make for an unmatched stretch of good winners.10

But which individual songs could be called the best or worst? At the bottom of the pile, there’s “Sweet Leilani” in 1937, “Buttons and Bows” in 1948 and “On the Atchison, Topeka and the Santa Fe” in 1946 (which Judy Garland sang). The worst performing songs of the past 20 years were “I Need to Wake Up” from “An Inconvenient Truth” (2006) and “Man or Muppet” from “The Muppets” (2011).

There’s a large clump of songs that won around 70 percent of their matchups, give or take 3 percentage points. Call this the great-but-not-best cluster. Then there’s a gap before you get to the truly differentiated tunes. The fourth- and third-ranked songs — “Flashdance (What a Feeling)” from “Flashdance” (1983) and “Can You Feel the Love Tonight” from “The Lion King” (1994), respectively — both won 77 percent of their matchups. The No. 2 song, “When You Wish Upon a Star” from “Pinocchio” (1940), won 80 percent.

But they’re no match for the best best original song of all time: Judy Garland’s rendition of “Somewhere Over the Rainbow,” from 1939’s “The Wizard of Oz,” won 91 percent of its matchups. That’s head and shoulders over the competition.

What’s the best best original song?

Oscar-winning songs and this year’s nominees by win percentage in a random matchup simulation

RK
Song
Year
Win Percentage
1 “Somewhere Over the Rainbow” 1939 91%
2 “When You Wish Upon a Star” 1940 80
3 “Can You Feel the Love Tonight” 1994 77
3 “Flashdance (What a Feeling)” 1983 77
5 “The Way You Look Tonight” 1936 73
6 “Fame” 1980 71
6 “Lose Yourself” 2002 71
6 “Rain Drops Keep Falling on My Head” 1969 71
9 “White Christmas” 1942 70
10 “My Heart Will Go On” 1997 69
10 “Que Sera Sera” 1956 69
10 “Under the Sea” 1989 69
13 “A Whole New World” 1992 68
13 “Let It Go” 2013 68
13 “Moon River” 1961 68
13 “Time of My Life” 1987 68
17 “Take My Breath Away” 1986 67
18 “Beauty and the Beast” 1991 66
18 “Skyfall” 2012 66
20 “Colours of the Wind” 1995 65
21 “Zip-a-Dee-Doo-Dah” 1947 64
22 “Streets of Philadelphia” 1993 63
22 “Theme From Shaft” 1971 63
24 “The Way We Were” 1973 62
25 “Last Dance” 1978 61
26 “Chim Chim Cher-ee” 1964 60
27 “Glory” 2014 59
28 “Baby, It’s Cold Outside” 1949 57
29 “Falling Slowly” 2007 54
29 “Up Where We Belong” 1982 54
29 “You’ll Be in My Heart” 1999 54
32 “I Just Called to Say I Love You” 1984 53
33 “All the Way” 1957 52
33 “Arthur’s Theme (Best That You Can Do)” 1981 52
35 “Born Free” 1966 50
35 “Swinging on a Star” 1944 50
37 “High Hopes” 1959 49
37 “I’m Easy” 1975 49
39 “Jai Ho” 2008 48
39 “Love Is a Many-Splendored Thing” 1955 48
41 “Mona Lisa” 1950 46
41 “You Light Up My Life” 1977 46
42 “It’s Hard Out Here for a Pimp” 2005 45
42 “Sooner or Later” 1990 45
42 “The Windmills of Your Mind” 1968 45
42 “Things Have Changed” 2000 45
47 “City of Stars” 2016 44
47 “If I Didn’t Have You” 2001 44
47 “Remember Me” 2017 44
47 “Thanks for the Memory” 1938 44
51 “Call Me Irresponsible” 1963 43
51 “Say You, Say Me” 1985 43
51 “The Morning After” 1972 43
54 “The Weary Kind” 2009 42
54 “We May Never Love Like This Again” 1974 42
54 “Writing’s on the Wall” 2015 42
57 “Al Otro Lado del Rio” 2004 41
57 “Into the West” 2003 41
58 “Evergreen (Love Theme From A Star Is Born)” 1976 40
58 “We Belong Together” 2010 40
58 “When You Believe” 1998 40
62 “Days of Wine and Roses” 1962 38
62 “It Goes Like It Goes” 1979 38
62 “Let the River Run” 1988 38
62 “Lullaby of Broadway” 1935 38
62 “Three Coins in the Fountain” 1954 38
62 “You’ll Never Know” 1943 38
68 “Gigi” 1958 37
68 “It Might as Well Be Spring” 1945 37
68 “Stand Up for Something” 2017 37
71 “For All We Know” 1970 36
71 “Man or Muppet” 2011 36
71 “Secret Love” 1953 36
74 “Mystery of Love” 2017 35
74 “Talk to the Animals” 1967 35
74 “This Is Me” 2017 35
77 “Never on Sunday” 1960 34
78 “The Shadow of Your Smile” 1965 33
79 “You Must Love Me” 1996 33
80 “The Last Time I Saw Paris” 1941 32
81 “The Ballad of High Noon” 1952 31
81 “The Continental” 1934 31
83 “Cool Cool Cool of the Evening” 1951 30
83 “Mighty River” 2017 30
85 “I Need to Wake Up” 2006 29
86 “On the Atchison, Topeka and the Santa Fe” 1946 28
87 “Buttons and Bows” 1948 22
87 “Sweet Leilani” 1937 22

Footnotes

  1. Suddenly” from “Les Miserables,” “Learn to Be Lonely” from “The Phantom of the Opera,” “I Move On” from “Chicago,” “Hopelessly Devoted to You” from “Grease” and “Mean Green Mother From Outer Space” from “Little Shop of Horrors.”

  2. Looking at you, “La La Land.”

  3. The Hands That Built America

  4. Vanilla Sky

  5. Dead Man Walkin’,” and “Streets of Philadelphia

  6. Blaze of Glory

  7. Can’t Stop the Feeling!

  8. My Funny Friend and Me,” “Until,” “You Will Be My Ain True Love” and “The Empty Chair

  9. Among our readers, at least.

  10. Note: FiveThirtyEight is owned by ESPN, which is partially owned by Disney.

Walt Hickey was FiveThirtyEight’s chief culture writer.

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