"[2] He played the role of Sheriff Joe Sutter in the musical The Spitfire Grill, where he introduced the song "Forest For the Trees."
In 2002, he played Robbie Faye in the New York production of A Man of No Importance and Archibald Craven at the Joey DiPaolo AIDS Foundation's concert of The Secret Garden alongside Michael Arden, Jaclyn Nedenthal, Will Chase, Max von Essen, Celia Keenan-Bolger, and Tony Award-winning actress Laura Benanti, whom he later married.
He was the lead actor for the NBC series Do No Harm, which premiered on January 31, 2013, to the lowest debut rating in the history of prime-time television.
He also starred in the Broadway production of the musical at the Gerald Schoenfeld Theatre beginning in late January 2014, with Kelli O'Hara replacing Elena Shaddow.
He had previously worked with O'Hara in 2013, in the world premiere of Richard Greenberg and Scott Frankel's musical Far from Heaven, in which he portrayed Frank Whitaker.
He received the 2016 Lucille Lortel Award for Outstanding Lead Actor in a Musical[9] for portraying Jamie Lockhart in the 2016 revival of The Robber Bridegroom at the Roundabout Theater Company.
In 2022, he portrayed Sky Masterson opposite his wife Phillipa Soo as Sarah Brown in the Kennedy Center production of Guys and Dolls.