You're going to LOL!
Kanye West – “The New Workout Plan” (2000)
Even without the video, the song is funny as hell. But when Kanye added these visuals, we were sure to bust a gut. The 8-minute video was absolutely hilarious and featured star-studded cameos by Anna Nicole Smith, John Legend, Tracee Ellis Ross, Vida Guerra, GLC and Fonzworth Bentley.
Ol’ Dirty Bastard – “Got Your Money” (1999)
Who doesn’t find a 70s pimp-slappin’ pimp chasing people around to collect his money funny? Not to mention, ODB is funny on his own. So this video is double the humor.
Biz Markie – “Just a Friend” (1989)
Another song that can stand on its own, “Just a Friend” is hilariously funny and a classic to this day. Biz being so dumbfounded in this video is cute, innocent, and funny. He was not here for blah, blah, blah and her shenanigans.