Comedians Who Wanted to Rock, and Got Their Big Chance

8. Bill Cosby, “Big Boss Man”

I don’t think it’s a shocker to anybody who watched his sitcom that Cosby is a fan of jazz. What comes as a surprise to me is that somewhere in-between being a legendary comedic storyteller, jazz musician, television star, and Jell-O spokesman, Bill somehow found the spare time to record and release an assload of music. Like, probably 15 albums of stuff not counting comedy records. Most of his “singing” was done for laughs, but there are a plethora of tracks that showcase his ability to carry a tune without needing to be goofy. I really have to recommend listening to his instrumental jazz albums, as well. There’s absolutely a reason that Cosby’s secured his position as a legend.