'Over the Rainbow,' 'Moon River' Among Greatest Oscar-Winning Songs of All-Time

by Julian Spivey

12. “City of Stars” by Ryan Gosling (La La Land)
Ryan Gosling is a white man who saves the genre of jazz in this Hollywood fairytale. It’s really good, despite this. The song that helps him save the genre is “City of Stars,” composed by Justin Hurwitz with lyrics by Benj Pasek and Justin Paul, the extremely catchy number from 2016’s “La La Land” that won Best Original Song at last year’s Oscars and will no doubt be in your head the remainder of the day. 

11. “I’m Easy” by Keith Carradine (Nashville)
Director Robert Altman wanted his actors in 1975’s “Nashville” to write and perform their own songs for his film. Keith Carradine wrote and performed two for the film, including the Oscar-winning “I’m Easy,” which became a top 20 Billboard hit and remains a lovely ballad to this day. 

10. “Theme from ‘Shaft’” by Isaac Hayes (Shaft)
Isaac Hayes’ “Theme from ‘Shaft’” is without a doubt one of the coolest Oscar-winning original songs with its soulfully funky sound. Hayes became the first African-American to win Best Original Song in 1971 and perhaps even more surprising is the fact he was the very first artist to win the honor for a song he both wrote and performed for the film – something that’s become much more common in the years since. 

9. “Raindrops Keep Falling on My Head” by B.J. Thomas (Butch Cassidy & the Sundance Kid)
“Raindrops Keep Falling on My Head” was written by Hal David and Burt Bacharach for 1969’s Western “Butch Cassidy & the Sundance Kid” and performed by B.J. Thomas, the third choice after Ray Stevens and Bob Dylan both turned it down. It’s honestly a weird selection for the movie as it plays over a fun scene where Paul Newman and Katharine Ross pal around on a bicycle, arguably a scene that could’ve been cut and not affected the movie in the least. 

8. “Lose Yourself” by Eminem (8 Mile)
Eminem made Academy Awards history when his “Lose Yourself” from “8 Mile,” in which he portrays a rapper based on his actual upbringing, became the first hip-hop song to win Best Original Song. To this day “Lose Yourself” is one of the greatest and most acclaimed hip-hop tracks of all-time. 

7. “Baby, It’s Cold Outside” by Esther Williams & Ricardo Montalban (Neptune’s Daughter)
“Baby, It’s Cold Outside” is one of two Christmas-related (though it wasn’t really intended as a holiday song) songs to win Best Original Song at the Oscars. Irving Berlin’s “White Christmas,” performed by Bing Crosby, in the film “Holiday Inn” won the Oscar in 1942. “Baby, It’s Cold Outside,” written by Frank Loesser, appeared in 1949’s “Neptune’s Daughter” performed by Esther Williams and Ricardo Montalban. It’s basically been recorded by everybody else in music since. 

6. “The Ballad of High Noon (Do Not Forsake Me)” by Tex Ritter (High Noon)
You don’t see too many movies open with a song that’s essentially a rundown of what you’re about to see, but “The Ballad of High Noon” does this brilliantly. Tex Ritter’s terrific performance of the Oscar-winner composed by Dimitri Tiomkin with lyrics by Ned Washington foreshadows the film’s ending that won Gary Cooper his second Best Actor award. 

5. “Moon River” by Audrey Hepburn (Breakfast at Tiffany’s)
“Moon River” is simply one of the most beautiful songs ever written. It was created by multiple time Oscar-winning duo of composer Henry Mancini and lyricist Johnny Mercer for the 1961 film “Breakfast at Tiffany’s.” The song is originally performed by Audrey Hepburn as main character Holly Golightly in one of the film’s most beautiful scenes. Believe it or not, Paramount Pictures executives wanted this scene cut because they didn’t like Hepburn’s performance. Hepburn essentially said, “Over my dead body” and it remained. 

4. “Falling Slowly” by Glen Hansard & Marketa Irglova (Once)
The great thing about the Academy Awards Best Original Song category is it allows for original songs from the smallest of movies to win an Oscar. This was the case for “Falling Slowly” from 2007’s Irish romance “Once,” a small budget release from director John Carney that featured real-life musicians Glen Hansard and Marketa Irglova who bond over their similar desire of music. It’s one of the most beautiful songs I’ve ever heard, period. 

3. “Over the Rainbow” by Judy Garland (The Wizard of Oz)
If you polled a large group of people on what the greatest movie song of all-time is the winner would likely be “Over the Rainbow” as performed by Judy Garland’s Dorothy in the 1939 classic “The Wizard of Oz.” The song, composed by Harold Arlen with lyrics by E.Y. Harburg, has become a music standard since its appearance in this film that is very likely the most watched film of all-time. The song appears just five minutes into the movie and honestly becomes its show-stopping scene. 

2. “Streets of Philadelphia” by Bruce Springsteen (Philadelphia)
Bruce Springsteen is likely the biggest rock star to ever win an Oscar for Best Original Song doing so for his excellent “Streets of Philadelphia” for director Jonathan Demme’s 1993 film “Philadelphia,” featuring Tom Hanks’ first Best Actor-winning performance as a man dying of AIDS. The song would not only win an Oscar, but also Song of the Year at the Grammy Awards, a rare feat for a song written for a movie. 

1. “The Weary Kind” by Ryan Bingham (Crazy Heart)
The Academy Awards have a great history of honoring country music portrayals. Sissy Spacek, Robert Duvall, Reese Witherspoon and Jeff Bridges have all won Oscar acting awards for great portrayals of both real and fictional country music singers. Ryan Bingham’s “The Weary Kind,” which he co-wrote with the film’s soundtrack producer T-Bone Burnett, essentially serves as the theme song for Bad Blake, Bridges’ character. “The Weary Kind” is a damn near perfect country song.