9. Home Movies (1999, UPN; 2001-2004, Cartoon Network)
Eight-year-old maverick director Brendon Small makes movies in his basement with the help of his regular crew, Melissa and Jason. He also plays a little soccer on the side, although his team never wins–no doubt due to the fact that their coach, McGuirk, is a washed-up alcoholic. Home Movies is the funniest show ever to appear on Cartoon Network’s Adult Swim. Comprised of hilarious, rambling conversations, witty movie parodies, and really cool original songs, Home Movies also boasted an excellent round-up of regular guest stars, including Jonathan Katz, Emo Phillips, Mitch Hedburg and Louis CK. But more than anything, it was the repartee between Brendon and his friends, teachers, and nemeses that really made the series so funny. For the record, John McGuirk is my favorite animated non-Simpsons character ever, and a personal hero of mine. The last episode of Home Movies was the saddest TV finale I’ve ever seen. The episodes are still funny on DVD or re-runs.
This is one of my favorite episodes: Brendon directs the school play (a take on Grease), convincing McGuirk to play the male lead (as well as drive his car onto the stage).