Ficou com o bichinho da representação após conseguir um pequeno papel na peça Prelude to a Kiss de Craig Lucas, numa audição para a qual um amigo o tinha desafiado a ir
Após a faculdade, mudou-se para Chicago, onde encontrou trabalho em comerciais de TV e estudou com os grupos de comédia Second City e ImprovOlympic (agora IO)
Teve o seu grande destaque como Sheldon o recepcionista do hotel em Almost Famous (2000)
Awards
2016Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:nominated
2015Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:nominated
2014Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:nominated
2013Golden Globe-Best Performance by an Actor in a Supporting Role in a Series, Miniseries or Motion Picture Made for Television:nominated
2013Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:winner
2012Golden Globe-Best Performance by an Actor in a Supporting Role in a Series, Miniseries or Motion Picture Made for Television:nominated
2012Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:winner
2011Golden Globe-Best Performance by an Actor in a Supporting Role in a Series, Miniseries or Motion Picture Made for Television:nominated
2011Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:winner
2010Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:winner
2009Screen Actors Guild Awards-Outstanding Performance by an Ensemble in a Comedy Series:nominated