He made his first ever debut in the movie named Loser in the year 2000 which is a teen comedy and it was followed by numerous guest spots in the episodes of NYPD Blue, Carnivale, Cold Case with some roles in the movie named D.E.B.S., Zodiac, Stay Alive and so on. In the year 2008, he starred in the Farnsworth Invention on Broadway. He had portrayed the character of Philo T. Farnsworth in the play and it was described as phenomenal by the Chicago Tribune which awarded him a Theatre World Award.
Starting from the year 2008 for about a year, he appeared as the character Lyle on The Late Show with David Letterman. During those time periods, he also made several appearances in the episodes of CSI, My Name is Earl, Psych and House; he also had supporting roles in the Date Night and The Invention of Lying. Other roles of him include Always Sunny on Philadelphia where he often appears as Liam McPoyle and in the A&E series Breakout Kings; he starred in the show was Lloyd Lowery.
In recent years, he appeared in the movie Abraham Lincoln: Vampire Hunter, White House Down and The Truth About Emanuel. He also appeared as in the movie House of Cards.
He met the actress whose named is Melanie Lynskey in the year 2001 when they both had to appear in the movie named Red Rose. They got engaged in the year 2005 and they eventually got married on 14th of April, 2007 in a chapel situated near Queenstown which is in New Zealand.
They had been living happily as a husband and wife until his wife filed a divorce in the year 2012, 25th September and she said that they had irreconcilable differences; ultimately, the divorce was finalized on 23rd of May, 2014. His interviews regarding this matter can be found in youtube. He is reported of having the net worth of 2 million USD according to the statistics and he earns a salary around 2.3 million in a year as per the reports. He also has been interviewed by several channels regarding his education and acting career since he was in his early 20s.