1. Kissing Jessica Stein (2001)
This is how he met still-girlfriend Jessica Westfeldt (who wrote and starred, whatever.) (photo via)
2. Providence (2000-2001)
Playing a fireman for 17 episodes. Studly. (photo via)
3. Gilmore Girls (2002)
GETTING BIG TIME. I actually remember this episode--his character turns out to be a total bore, which is absurd, because he offers to take Lorelai to a BOWIE concert. Come on, lady, use your head. Or your eyes.
4. Charmed (2005)
That is an unfortunate butt cut.
5. Ira & Abby (2006)
Here's another movie in which irritatingly pretty girlfriend stars, and Jon kind of moonlights in the background. Again with the unfortunate hair. (It's on Netflix Instant right now if you have some time to kill.)
6. The Ten (2007)
Regrettable movie, regrettable facial hair. (Also on Netflix Instant.)