He later joined the cast of NBC police drama Hill Street Blues playing Detective Harry Garibaldi from 1984 to 1985, and from 1985 to 1986 co-starred on the CBS prime time soap opera Falcon Crest as Father Christopher Rossini.

Olin also guest-starred on Murder, She Wrote and Hotel before he was cast as Michael Steadman, one of the lead roles in the ABC drama series Thirtysomething.

He appeared along with wife Patricia Wettig in the 1995 television film Nothing But the Truth, and well as in Telling Secrets (1993) with Cybill Shepherd, The Advocate's Devil (1997) alongside Mariska Hargitay, and Evolution's Child (1999).

From 2007 to 2011, Olin had a recurring role opposite wife Patricia Wettig in the ABC drama series Brothers & Sisters.

In 2020, ABC ordered a sequel for Thirtysomething and Olin was set to return alongside Mel Harris, Timothy Busfield and Patricia Wettig; however, the project remains in development limbo.

[7] Olin was born to a Jewish family[8] in Chicago, Illinois, the son of a former Peace Corps official and pharmaceutical company owner.