"Ole Buttermilk Sky" was a big hit in 1946 for big band leader and old-time radio personality Kay Kyser (1905–1985), and composer country western music singer Hoagy Carmichael (1899–1981), plus other artists. It has been covered by a multitude of artists / singers over the years and decades since. The following year of 1947, it was nominated for an "Oscar" as the Academy Award for Best Original Song at the 19th Academy Awards ceremony in March 1947 at the Shrine Auditorium in Los Angeles, California.

The song was composed by Hoagy Carmichael (1899–1981), and Jack Brooks (1912–1971),^[1] and introduced by Carmichael^[2] in the Western film Canyon Passage (1946), starring Dana Andrews, Brian Donlevy, Susan Hayward, Patricia Roc, Ward Bond and Andy Devine, (with a bit appearance by Hoagy Carmichael, singing the song himself).

"Ole Buttermilk Sky" was primarily written as a cowboy song to set the scene where the character meets his lover.^[3] The song also used jazz music for the lyric "can't you see my little donkey and me".^[4]

It was recorded in the December 14 issue of The Billboard magazine that "Ole Buttermilk Sky" by big band / orchestra leader and old-time radio personality Kay Kyser was at #1 in the Best Selling Popular Retail Records section. Having moved up two notches from its previous position of #3, it had been in the chart for the past seven weeks. A later version by Helen Carroll and the Satisfiers (1914–2011), was at #8. Paul Weston (1912–1996) with his billed ensemble of Paul Weston and his Orchestra with Matt Dennis (1914–2002) as vocalist singer, had their versions at #9.^[5]

For the week ending December 14, 1946, in the Most Played Juke Box Records chart, it showed that the song was getting many plays and there were five versions getting attention. Kay Kyser's version on Columbia 37073 had been on the chart was at #2. Hoagy Carmichael's version was at #5. Paul Weston and his Orchestra with Matt Dennis were at #9. Helen Carroll and the Satisfiers were at #15. And a new version by female singer Connee Boswell (1907–1976), was coming up the charts.^[6]

"Ole Buttermilk Sky" was nominated for an "Oscar" as the Academy Award for Best Original Song at the 19th Academy Awards ceremonies / show at the Shrine Auditorium in Los Angeles, California in March 1947.^[7]