The signature jazz track by Miles Davis was released in 1959 on the album, “Kind of Blue.” It featured Davis on trumpet, Cannonball Adderley on alto saxophone, John Coltrane tenor saxophone, Wynton Kelly piano, Paul Chambers bass, and Jimmy Cobb drums. Based on a 12-bar blues progression, Miles used the structure’s simplicity to capture the spontaneity of the musicians and their solos in the first take. “Freddie Freeloader” was the first track recorded for “Kind of Blue.”
Some people believe the song’s title refers to a guy named Freddie who’d try to get into shows to hear Miles and other jazz artists play, without paying.
Others point to Clown Hall of Fame inductee, and multiple Emmy award broadcaster, Red Skelton, whose most famous character was a sad clown named, “Freddie the Freeloader.”
According to Skelton, Freddie has, “found out what love means. He knows the value of time. He knows that time is a glutton. We say we don’t have time to do this or do that. There’s plenty of time. The trick is to apply it. The greatest disease in the world today is procrastination. And Freddie knows about all these things. And so do you.”