Rogers was raised in Newport Beach, California. After high school, he attended several colleges, finally attending the Yale School of Drama, graduating in 1993.
Rogers was nominated for the 1996 Tony Award for Best Featured Actor in a Play and the 1996 Drama Desk Award for a Broadway revival of Philip Barry's Holiday. He won the 2002 Obie Award as Outstanding Actor for his role in Richard Greenberg's Off-Broadway play The Dazzle.
In May 2005 he costarred with Marin Hinkle in the Craig Lucas adaptation of the August Strindberg's Miss Julie at Rattlestick Playwrights Theater.
In 2011 he performed in two plays at Shakespeare in the Park in New York City: Measure for Measure and All's Well That Ends Well. In September 2011 he appeared in the new Theresa Rebeck play Poor Behavior at the Mark Taper Forum, Los Angeles.
In August 2013 Rogers costarred with Johanna Day in the world premiere of Carly Mensch’s play Oblivion at the Westport Country Playhouse.
In March 2017 he began performing as Morris Dixon in the Broadway production of Present Laughter starring Kevin Kline.
