“Freddie Freeloader” is a composition by Miles Davis and is the second track on his 1959 album Kind of Blue. The piece takes the form of a twelve-bar blues in Bb, but the chord over the final two bars of each chorus is an bVII7, the backdoor dominant to go back to I7.

The origin of the title is disputed. Jon Hendricks and Kind of Blue chronicler Ashley Kahn claim that Fred Tolbert was a Philadelphia bartender whose business card read “Freddie the Freeloader”. According to the documentary Kind of Blue: Made in Heaven, and an anecdote from the jazz pianist Monty Alexander, the piece was named after an individual named Freddie who would frequently try to see the music Davis and others performed without paying (thus freeloading).

Jon Hendricks added vocalese-style lyrics to all of the original solos, reimagining it as a story about a barman who allowed jazz musicians to freeload at his bar at the expense of other patrons.

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