Seven unworthy songs that should have never won a Best Song Oscar

1937

Winner: “Sweet Leilani”
Should have won: "They Can't that Away from Me"

 I said that not all the incorrect winners were bad songs. Here’s a glaring exception. This may be the most egregious mistake in the history of the award. “Sweet Leilani,” written by Harry Owens a day after his daughter was born, just isn’t a very good song. It was a popular song, true. And if you like Chris Isaak’s 1996 cover, please forgive me. To me, it’s just kind of sappy, bordering on bathetic. Even Bing Crosby’s voice couldn’t rescue the original.

On the other hand, Fred Astaire sang the Gershwin brother’s gorgeous “They Can’t Take That Away From Me” to a glowing, soft-focus Ginger Rogers in Shall We Dance that same year and it melted hearts. The movie is light years better than Waikiki Wedding, which doesn’t matter for the award. But the song is also such a timeless classic. Ira asked Astaire to sing it at his brother’s memorial concert. Nobody better be singing “Sweet Leilani” at my funeral.

1943

Winner: “You’ll Never Know”
Should have won: "That Old Black Magic"

This gets trickier. There’s nothing wrong with Alice Faye’s recording of the Harry Warren/Mack Gordon love song, “You’ll Never Know.” It’s a sweet, fairly standard tune. And when you listen to Johnny Johnson’s delivery of Harold Arlen and Johnny Mercer’s “That Old Black Magic” from Star Spangled Rhythm, you might genuinely prefer “You’ll Never Know.” This is where we have to distinguish between song and production.

“That Old Black Magic” is a much better song, but Johnson does it no favors with his stilted, dated delivery. Listen to Frank Sinatra sing it with a Billy May arrangement behind him and you’ll realize just how much more there was to this song. It had room to grow, unlike “You’ll Never Know,” which was pretty much fully formed in the Alice Faye rendition.

By the way, this is the same logic that allows me to be OK with “What Was I Made For?” winning this year. It’s a great song with a production that I don’t like very much. The award goes to the songwriters, so I’m going with “Black Magic” in ’43. But if you want a third-party compromise choice, Cole Porter’s “You’d Be So Nice to Come Home To,” sung by Janet Blair and Don Ameche in Something to Shout About, would be a worthy winner as well.