In 2014 he starred in the independent love drama Comet, which he and his co-star Emmy Rossum also produced. On August 16, 2010, he co-hosted WWE Raw with Going the Distance co-stars Charlie Day and Jason Sudeikis at the Staples Center in Los Angeles. From July 7–18, 2010, he appeared in a production of Samuel J. Long read the audiobook version of Judy Blume's Then Again, Maybe I Won't and Stephen King's Everything's Eventual. He was cast as a one-armed Civil War veteran in Robert Redford's The Conspirator. Also in 2010, Long starred in the comedy film Going the Distance with Drew Barrymore. He also provided the voice of Humphrey in Alpha and Omega (2010), starring with Hayden Panettiere. In 2009, he starred in He's Just Not That Into You along with co-star Ginnifer Goodwin and After.Life opposite Liam Neeson and Christina Ricci. Long also had a small role in the comedy film Zack and Miri Make a Porno (2008), where he plays Brandon St.
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The campaign featured commercials in which Long as a Mac and John Hodgman as a PC engaged in playful banter about "the strengths of the Mac platform and weaknesses of the PC platform." Long is known for his depiction of a Mac in Apple's " Get a Mac" campaign. In 2007, he co-starred with Bruce Willis as a " white-hat hacker" in Live Free or Die Hard and had a role in the comedy The Sasquatch Gang. Long made a guest appearance in the documentary, Wild West Comedy Show (2006). He also played the main character in the comedy film Accepted (2006).
He was the voice of the character Alvin in Alvin and the Chipmunks, Alvin and the Chipmunks: The Squeakquel, Alvin and the Chipmunks: Chipwrecked, and Alvin and the Chipmunks: The Road Chip.
He was offered the opportunity to replace Steve Burns on Blue's Clues after he left the show, but ultimately declined.
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He was also a regular on the NBC TV series Ed (2000–04), playing socially awkward Warren P. Long's film credits include Idiocracy, Waiting., Jeepers Creepers, DodgeBall: A True Underdog Story, The Break-Up, Crossroads, Galaxy Quest, Dreamland and Live Free or Die Hard. Long at the 2007 Toronto International Film Festival