Schiff made his television directorial debut with The West Wing, directing an episode titled "Talking Points".

He had a leading role in ABC's medical drama The Good Doctor, as Dr. Aaron Glassman, president of a fictional teaching hospital in San Jose, California.

[5][6] His early jobs before acting included driving a taxi in New York City and cleaning buses in the Greyhound terminal on 11th Avenue.

[11] In the early 1990s, Schiff landed numerous small roles in a variety of films, including a Train Driver in Speed.

Gen. Robert Laurel Smith in the 1998 HBO TV movie The Pentagon Wars, based on the real-life development of the US Army's Bradley Infantry Fighting Vehicle.

He played the part of the tough lawyer Mr. Turner in I Am Sam opposite Sean Penn and Michelle Pfeiffer and co-starred in People I Know with Al Pacino.

He also starred in the premiere run of Underneath the Lintel, a one-act, single-character play by Glen Berger, at the George Street Playhouse in New Brunswick, New Jersey.

Later that year Schiff co-starred in Last Chance Harvey with Dustin Hoffman and Emma Thompson and Another Harvest Moon with Ernest Borgnine and appeared in the season finale of Eli Stone.

Schiff portrayed Charles Fischer in Terminator: The Sarah Connor Chronicles in the Season 2 episode "Complications".

Later in 2009, he returned to London to shoot two other movies: The Infidel,[12] in which he starred opposite Omid Djalili, and Made in Dagenham, with Sally Hawkins and Bob Hoskins.

[13] He also has guest-starred on Any Human Heart with Jim Broadbent playing the role of a psychiatrist and on White Collar's second-season episode 15.

Schiff played an important plot character in three episodes of CBS's NCIS, bridging seasons 9 and 10, as Harper Dearing, the replacement for Osama bin Laden on the Most Wanted Wall for attacks against the United States Navy.

He had a recurring guest role in the TV series Once Upon A Time and joined Helen Hunt and former West Wing star Bradley Whitford in the movie Decoding Annie Parker.

He portrayed Erie Smith in a revival of the Eugene O'Neill play, Hughie, at the Shakespeare Theatre Company in Washington, D.C., in February and March 2013, and Dr. Emil Hamilton in Zack Snyder's 2013 Superman film, Man of Steel.

In September 2014, Schiff returned to the West End in a revival of Speed-the-Plow by David Mamet, co-starring Lindsay Lohan.

Schiff appeared on Mom in the episode "Pure Evil and a Free Piece of Cheesecake", in which he was reunited with his West Wing co-star Allison Janney.

He provided the facial and motion capture, and voice for Odin in Santa Monica Studio's game God of War Ragnarök, released in 2022.

[19] On November 10, 2020, Schiff announced that he and his wife had tested positive for COVID-19 on Election Day and were quarantining at their home in Vancouver.