“Freddie Freeloader” by Miles Davis

Second in line on Kind of Blue, Miles Davis's 1959 album, "Freddie Freeloader" is a Davis blues with a twist: it runs twelve bars in B-flat, but over the last two bars of each chorus it lands on an A-flat 7 instead of the usual B-flat 7 and turnaround.

Davis sat Bill Evans out and brought in Wynton Kelly, who had a name as a blues man, and Kelly, Davis, John Coltrane on tenor, Cannonball Adderley on alto and Paul Chambers on double bass all take solos, with Jimmy Cobb on drums. Nobody can quite agree on the title: a Philadelphia bartender, a character who kept trying to hear the band without paying, and Red Skelton's hobo clown have all been named. Jon Hendricks later set vocalese words to the solos, singing Coltrane's part himself, and turned it into the tale of a barman who let jazz players freeload.

Written with AI assistance from RockLists chart data, MusicBrainz and Wikipedia.