Reggie Watts, Flight of the Conchords and MonoNeon have a lot of songs/youtube videos that are both very funny and awesome music.
Jazz “Education”
Jacob Mann’s One Minute Jazz Lessons series
Hans Groiner
++++The Music of Thelonious Monk
++++Jazz Piano Lesson
Shreds
Miles
++++Tutu
++++Miles and Coltrane
++++My very funny Valentine
Miscellaneous
Keith Jarrett at Umbria
++++I do not speak Italian
++++Incident at Umbria