Skerritt was born in Detroit, Michigan, the son of Helen, a homemaker, and Roy Skerritt, a businessman. A 1951 graduate of Detroit's Mackenzie High School, Skerritt attended Wayne State University and the University of California at Los Angeles. Since 1988, he has divided his domestic life between his Lake Washington home in suburban Seattle, Washington and a home on Lopez Island in the San Juan Islands.
Skerritt made his television debut in the series Gunsmoke around 1959 and his film debut in War Hunt, produced by Terry Sanders and released the same year. Skerritt has appeared in over 40 films and more than 200 television episodes since 1962.
Skerrit starred in the television series Picket Fences (1992–1996) in the role of Sheriff Jimmy Brock, for which he won an Emmy. More recently, he has starred in Homeland Security and The Grid.
He also portrays the deceased William Walker on Brothers & Sisters, having appeared in the pilot as well as in several flashbacks since. This is his second time playing the husband of Sally Field, the first being his role in the film Steel Magnolias. He played the role of Ezekiel on ABC Family's Fallen miniseries. He also appeared as the guide on the showcase website for Microsoft's Windows Vista operating system.
He will guest star in season 3 of Leverage as Nate Ford's father.
Skerritt has four grown children (three sons and one daughter) and an adopted daughter with his current wife.