Top Twenty Academy Award Best Original Song Winners
(Of the 92 Best Original Song winners so far, I appreciate a little fewer than half of them, but among those are some true classics. Here are my twenty favorites, in order of preference.)
“Over the Rainbow” as performed by Judy Garland
“Moon River“ as performed by Audrey Hepburn
“When You Wish Upon a Star“ as performed by Cliff Edwards
“Falling Slowly“ as performed by Glen Hansard and Markéta Irglová
“The Windmills of Your Mind“ as performed by Noel Harrison
“The Ballad of High Noon“ as performed by Tex Ritter
“The Way You Look To-night“ as performed by Fred Astaire
“Take My Breath Away“ as performed by Berlin
“I’m Easy“ as performed by Keith Carradine
“Theme from Shaft“ as performed by Isaac Hayes
“All the Way“ as performed by Frank Sinatra
“Raindrops Keep Fallin’ on My Head“ as performed by B. J. Thomas
“Baby It’s Cold Outside“ as performed by Esther Williams and Ricardo Montalbán, Betty Garrett and Red Skelton
“Swinging on a Star“ as performed by Bing Crosby
“White Christmas“ as performed by Bing Crosby
“It’s Hard Out Here for a Pimp“ as performed by Terrence Howard and Taraji P. Henson
“Zip-a-Dee-Doo-Dah“ as performed by James Baskett *
“Under the Sea“ as performed by Samuel E. Wright
“Mona Lisa“ as performed by Sergio de Karlo
“Up Where We Belong” as performed by Joe Cocker and Jennifer Warnes
* I know, but can you blame the song?
— August 10, 2026