Academy Awards: 5 Oscar-Nominated Songs That Should Have Won But Didn’t

Should Have Won: “A Kiss At The End Of The Rainbow” from A Mighty Wind, 2003

When a little ditty with heart that is simultaneously mocking itself can sneak itself into the running for Best Original Song at the Oscars, we say, “Hip, hip, hooray!” Christopher Guest’s characters Mitch and Mickey (Eugene Levy and Catherine O’Hara) perform the song at a pivotal point in the movie A Mighty Wind and we are whisked away into a flurry of mixed emotions — this being a good thing! The music and lyrics by married-to-each-other actors Michael McKean and Annette O’Toole are both sweet and syrupy, but hysterical all the same,because of the actors’ committed delivery: “My sweet, my dear, my darling, you’re so far away from me / Though an ocean of tears divides us, let the bridge of our love span the sea.” And we die. Comedic brilliance marries sweet sentiment, and born is a song so sincere that it’s both touching and hilarious. Now that deserves Oscar gold, if not a pot of gold.

Winner: “Into the West” from The Lord of the Rings: The Return of the King