Funkiest Jam: The Wolverines "Jazz Me Blues"
Leon Bismark "Bix" Beiderbecke could easily be a Harry Potter character, and he did execute wizardry with a cornet and piano. Thanks to a gift for improvisation, Bix is often credited with the invention of "cool jazz," an innovation on the jazz ballad style.
Beiderbecke learned how to play the cornet (the trumpet's cousin) by ear, making him essentially a Jazz Game Jimi Hendrix. Jimi's right-handed guitars were turned upside-down and restrung for left-hand playing, giving him an unorthodox sound. In much the same way Beiderbecke's self-taught, unorthodox fingering allowed him to create a unique sound that other trumpeters and cornetists couldn't match. Biz's counterpart was Louis Armstrong, and their rivalry was like Magic Johnson and Larry Bird. One was more flashy and charismatic (Armstrong) while the other was understated and tenacious, preferring not to dazzle the audience with theatrics (Beiderbecke).
Ironically, and fittingly for this list, Bix's most influential works happened during his time with the Paul Whiteman Orchestra. Critics laud him as one of the funkiest jazz musicians in history, and one of the only white guys to ever significantly shift or advance the direction of the genre.