Original Show: Undeclared
Played By: Loudon Wainwright III
The Pitch: Much like Freaks and Geeks, Undeclared ended far too soon, forcing viewers to part with a hilarious cast. Loudon Wainwright III's portrayal of the doofy, well-intentioned Hal Karp was one of the most memorable parts of Judd Apatow's take on university life.

Now that Apatow has moved into producing work about folks facing mid-life crises, the pairing of actor and creator would be a perfect fit. Watching LWIII try to keep his life together post-divorce would make for great lonely laughs. As a special bonus, LWIII, who your mom and dad know better as a singer-songwriter, could hit audiences with tunes as he sees fit.