Ben Folds: Rockin’ the Suburbs (2001)
For his first solo effort post-Ben-Folds-Five, Ben Folds decided to play every instrument. It thus makes sense that, in the video, he indeed plays every instrument. Mix in suburbia and a healthy dose of awkward dancing and you have…well, this video. What’s the link to Weird Al? He directed it, and has a cameo appearance.
Weird Al Yankovic: The Saga Begins (1999)
Weird Al summarizes The Phantom Menace in five minutes and sets it to Don McLean’s “American Pie”. I get the feeling that his entire career led to this one song.