Schiff, the middle of three sons, was born in Bethesda, Maryland, the son of Charlotte, a television and publishing executive, and Edward Schiff, a real estate lawyer.

Schiff initially disliked acting and studied to be a director. He directed several off-Broadway plays, including "Antigone" with a then just-graduated Angela Bassett in 1983.

He met present wife, Sheila Kelley, during auditions for this play.

In 1996 Schiff guest starred on the popular TV series ER, and appeared in NYPD Blue the following year.

Schiff played a doctor alongside Eddie Murphy in the 1998 Dr. Dolittle remake.

He also played Col./Brig. 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.

In 2004, Schiff appeared in Ray as famed musician Ray Charles's producer, Jerry Wexler.

In this movie, he shaves off his trademark beard. After starring on The West Wing since 1999, Schiff chose to leave the series in its seventh season (2005–2006), and was contracted to appear in half of the season's episodes.


In early 2006, Schiff returned to his stage roots, starring 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.

In February 2007, he appeared in West End production of Underneath the Lintel in the Duchess Theatre in London, England, and also appeared on BBC Radio Five Live and talked at length to Simon Mayo about his experience of acting in the West Wing and his new West End production.