On Broadway, he has originated roles in Waitress, Kinky Boots, The Last Ship, Rocky, and Soul Doctor, and was nominated for a Drama Desk Award for Outstanding Actor in a Musical.

His performances on the West Coast have included Don Quixote in Man of La Mancha, Dr. Frank N. Furter in The Rocky Horror Show, Richard M. Nixon in Judy's Scary Little Christmas, and Burrs in both versions of The Wild Party.

In 2009, Anderson made his Broadway debut as Stewpot in the Tony award-winning revival of South Pacific at Lincoln Center.

Anderson was nominated for a Drama Desk Award for Outstanding Actor in a Musical[7] for his portrayal in the pre-Broadway production at New York Theatre Workshop.

Anderson portrayed Mr. O'Malley in The Greatest Showman (2017), and has had guest roles on television, including Elementary, The Good Wife, Law & Order: Criminal Intent and Alias.