He had a role in the 1997 CBS adaptation of the book True Women and had a starring role in the 2000 film Lone Star Struck. In 2001, he won Best Actor at the International Teen Movie Festival (ITMF) in Vaughan, Ontario, Canada for his role in his short film Head Shot. He also received praise in 2001 in an article in Newsday, and this helped further his career. He appeared as a member of the First Regiment of Virginia Volunteers in the 2003 Civil War film Gods and Generals, which starred Robert Duvall. Fisher parodied actor Tom Cruise in the 2008 film Superhero Movie. He had a recurring role as a rookie police officer in 2008 on the television series The Cleaner on A&E Network. Fisher appeared in 2009 on Gossip Girl. On the third season of the television series Mad Men, Fisher portrayed a friend of character Paul Kinsey.