My mom bought me a Run-DMC video compilation as an Easter present this year (because she’s awesome), so this could be called “Video In My Head #1.” Run-DMC has a lengthy list of classic tracks and groundbreaking videos, but “It’s Tricky” (from 1986’s Raising Hell) always has been my favorite combination of the two. (I could tell you my favorite part of the twist ending featuring Penn and Teller, but that would spoil the whole thing. If you guess what it is, tell me in the comments!)
Rest in peace, Jason Mizell. There are lots of cool musicians named Jay, but there is only one Jam Master Jay!