Gained wide recognition for his roles on the television series Walking Dead, Supernatural, and Grey's Anatomy. He also played the role of The Comedian in Zack Snyder's film Watchmen.
He was a basketball player in high school and college and was later employed as a graphic artist.
He played Judah Botwin on the television series Weeds. He played Jason Crouse on The Good Wife from 2015 to 2016.
He married actress Hilarie Burton in 2014. They have a son named Gus together. In September 2017, they confirmed they were expecting their second child together.
He was briefly engaged to Weeds co-star Mary-Louise Parker in 2008.