Lewis was cast in the title role of the short-lived 1991 situation comedy, Teech. The show was cancelled after only four episodes. He appeared in guest parts on various television series including Pacific Blue, JAG, Ally McBeal, Joan of Arcadia, Brothers & Sisters, 8 Simple Rules, Buffy The Vampire Slayer, Friends and How I Met Your Mother. Lewis has also had recurring roles on A Different World, The Wayans Bros., Lizzie McGuire, Yes, Dear, Scrubs, and Raising Hope.
Lewis co-starred in the Disney Channel original series The Suite Life of Zack & Cody as Mr. Moseby. Since 2008, he has reprised the role on a spin-off The Suite Life on Deck, where he plays the manager of The S.S. Tipton. He has appeared as a guest star on Disney Channel's That's So Raven and Phineas and Ferb and also in one of the channel's original films, Dadnapped. On the children's show Special Agent Oso he has a recurring role as the voice of Agent Wolfie.
In addition to his television work, Lewis has appeared in several films. He made his film debut as Dennis in the 1989 dark comedy Heathers. He has appeared in smaller roles in more than a dozen films, including City Slickers (1991), Bowfinger (1999), I Spy (2002), Surviving Christmas (2004), Kicking & Screaming (2005), and Beverly Hills Chihuahua 2 (2011).
As a television director, he directed several episodes of The Suite Life on Deck, first making his directorial debut in The Suite Life of Zack & Cody episode "I Want My Mummy" (2007). He has since gone on to direct episodes of the Disney Channel sitcoms A.N.T. Farm, Austin & Ally, Good Luck Charlie and Jessie starring his former Suite Life on Deck co-star Debby Ryan.
Lewis is the son of former Chesapeake and Potomac Telephone executive and former U.S. Ambassador Delano Lewis. He was in Uganda, East Africa during his father's stint as Peace Corps' associate director and country director for Nigeria and Uganda. He has a wife and three children. A boy named Harry Lewis (March 26, 2002) a girl Christy Lewis (June 24, 2005) and another boy named Kendall Lewis (April 23, 2010). His wife is named Jessica Lewis and got married on April 13, 2001.