Made TV debut in an episode of "The Guardian" (CBS)
Feature film debut, "Sleepover"
Cast as Silas Botwin, the oldest son of a drug dealing suburban mother, in Showtime's "Weeds"
Played the son of Jeff Daniels and Kristin Chenoweth in the comedy "RV"
Played Ben Samuels, the only white student in a California high school class, in "Freedom Writers"
Began hosting a web talk show with his friends Kyle Sherman and Allison Tyler called "Two Guys and a Girl"
Joined the cast of the Tony-Award-winning Broadway musical "Spring Awakening" playing the lead role of Melchior Gabor
Appeared as a high-school basketball player in the film "17 Again"
Cast as Meryl Streep and Alec Baldwin's son in Nancy Meyers' "It's Complicated"