1. 1. 1995- Our favorite brother/love interest Josh in Clueless 2. Via tumblr.com 2. 1996- Protagonist and tight pants wearing Paris in Romeo + Juliet 3. 3. 1998- Gay bestie/lover of JenAn in the late-night Lifetime special Object of My Affection. 4. imdb.com / Via imdb.com 4. 1999 War hero and victim of adultery- Lt. Wally Worthington in The Cider House Rules 5. images.suite101.com / Via images.suite101.com 5. 2000- Who can forget his role as the naive and curious Nick Carraway, in the made for TV hit The Great Gatsby. 6. Via images.profileengine.com 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. cdn.chud.com / Via cdn.chud.com 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. 8. Or this...Dave- 40 Year Old Virgin, 2005 9. 9. Oh come ON obviously this!Pete- Knocked Up, 2007 10. media.onsugar.com / Via media.onsugar.com 10. Whoops probably not that...Adam- I Could Never Be Your Woman, 2007 11. imdb.com / Via reviewstl.com 11. But definitely from any of these...keep em coming!