In some circles, the Academy Awards are discussed more for those who didn't win rather than those who did. But, contrary to what certain pundits may have you believe, there are plenty of worthy Oscar winners every year, and the Best Original Song category stands out as fertile ground for exceptional artistic achievements.

This post will walk you through a brief overview of the 15 greatest songs ever to win the golden statuette, going all the way back to when the category was first introduced in 1934, for the seventh edition of the world-famous awards show.

Because I wanted an actual film critic to weigh in on this topic, this write-up features insight from @Kevin Pettit, the creator of the fabulous See You At The Movies newsletter here on Substack. If you’re interested in the current cinema and need a reliable voice to turn to for recommendations, subscribe to his feed and thank me later.

Before we get started, a quick reminder to click the “Subscribe” button if your finger feels so inclined.

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In chronological order, let’s go:

1. "Over the Rainbow" – The Wizard of Oz (1939)

Matt:

One of the most recognizable songs ever written and performed for a film, Judy Garland’s version of “Over the Rainbow” remains the definitive version of this classic track. Interestingly, the film version wasn’t available for fans to buy until 1956, when MGM released a full-fledged soundtrack to coincide with The Wizard of Oz’s first TV showcase. The most recent digital remaster is an excellent reminder of how incredible Garland’s voice was against this kind of arrangement.

Another enjoyable aspect of this song’s legacy is how many well-known artists have covered “Over the Rainbow” in the years since the film debuted in cinemas. Everyone from Aretha Franklin and Ray Charles to Jerry Lee Lewis and Glenn Miller have released their versions, and that’s just the tip of the iceberg. It’s a fun rabbit hole to wander down if you’ve got a few spare minutes.

Kevin:

TBD

https://www.youtube.com/watch?v=8TOBzT-1LfU&pp=ygUdb3ZlciB0aGUgcmFpbmJvdyB3aXphcmQgb2Ygb3o%3D

2. "Moon River" – Breakfast at Tiffany’s (1961)

Matt:

Composed by the great Henry Mancini and Tin Pan Alley lyricist Johnny Mercer, “Moon River” was one of the first legitimate pop blockbusters that originated from a film soundtrack. On top of winning the Best Original Song Oscar, it also snagged Grammys for Record of the Year and Song of the Year. Heard in the context of the film’s intro, it has to be one of cinema’s most indelible sonic character introductions.

While Hepburn originally sang the song to great effect, “Moon River” is more commonly associated with crooner Andy Williams, who recorded his version in 1962 and was the one tapped to perform it at that year’s Oscar ceremony. It ended up becoming such a massive success for him that he’d eventually title his memoir “Moon River” and Me. Branding synergy, amirite?