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 has frequently appeared in guest roles on television shows including Law & Order, CSI: Crime Scene Investigation, Friends, Boardwalk Empire, The Knick, Lipstick Jungle, Miss Match, the TV miniseries Attila, and Hell on Wheels. He played the killer Andrew Lincoln in the 2005 TV film Stone Cold, part of the Jesse Stone TV film series.

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 the 2014 Broadway production of You Can’t Take It With You, he played Boris Kolenkhov, the Russian refugee and dance teacher.

In March 2017, he began performing as Morris Dixon in the Broadway production of Present Laughter starring Kevin Kline.