The first Grammy Awards were held on May 4, 1959. Though mainly considered to be “music’s biggest night,” one category that’s stuck around in some capacity since that inaugural ceremony is Best Comedy Performance (or as it’s now known, Best Comedy Album). In more recent years, the award has been given out almost exclusively to stand-up comedians, with Dave Chappelle having won it six times in the last decade—leaving him just one award away from surpassing Bill Cosby, who holds the current record in the category with seven wins to date.
Stand-up wasn’t always the main focus, however. There have been times when albums by comedy teams got nominated and even won, as well as musical comedy recordings by the likes of “Weird Al” Yankovic and Peter Schickele. Speaking of the first Grammys, though, that year’s show was especially interesting because of the variety of artists who were nominated for Best Comedy Performance. In the running for the award were stand-up pioneer Mort Sahl for his album The Future Lies Ahead, comedy duo Nichols and May for their debut recording Improvisations to Music, and satirist Stan Freberg for two separate projects: the 1958 compilation The Best of the Stan Freberg Shows, and a Christmas song called “Green Chri$tma$.”
Unfortunately for all of them, it would be a different Christmas song that would take home the award for Best Comedy Performance that evening, and it’s one you’ve absolutely heard before. The song in question was “The Chipmunk Song (Christmas Don’t Be Late),” by Ross Bagdasarian, otherwise known as the voice of Alvin and the Chipmunks. You know the tune…
The novelty Christmas carol was a surprise megahit in its day and spent four weeks in the No. 1 spot on the Billboard charts during the 1958 holiday season. It’s re-entered the Billboard Hot 100 several times since then, including when the 2007 live-action Alvin and the Chipmunks film was released. It also won the award for Best Recording for Children at the 1st Annual Grammys and was even nominated for Record of the Year that year. And as if that wasn’t enough, the album on which the song was eventually released won the Grammy for Best Album Created for Children in 1961.
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