1. 1995- Our favorite brother/love interest Josh in Clueless
2. 1996- Protagonist and tight pants wearing Paris in Romeo + Juliet
3. 1998- Gay bestie/lover of JenAn in the late-night Lifetime special Object of My Affection.
4. 1999 War hero and victim of adultery- Lt. Wally Worthington in The Cider House Rules
5. 2000- Who can forget his role as the naive and curious Nick Carraway, in the made for TV hit The Great Gatsby.
6. 1, 2 skip a few (years) to his recurring role on Friends as Pheobe’s foolishly charming boyfriend-turned husband: Mike Hannigan from 2002-2004
7. And just incase you forgot who we’ve been talking about…maybe you’ll recognize him from this:
Brian Fantana- Anchorman: The Legend of Ron Burgundy 2004
8. Or this…
Dave- 40 Year Old Virgin, 2005
9. Oh come ON obviously this!
Pete- Knocked Up, 2007
10. Whoops probably not that…
Adam- I Could Never Be Your Woman, 2007