After spending nearly two decades with Steppenwolf, Perry moved to Los Angeles in 1987 to pursue film and television work.

He replaced John Billingsley in the role of Terrence Steadman in the critically acclaimed TV show Prison Break(2006) Perry also has been in multiple stage productions.

He starred in the Tracy Letts play August: Osage County on Broadway, which originated at Steppenwolf Theatre in Chicago.

During the production, he said "During Anna Christie the biggest challenge I had was working with my daughter and sort of not stopping and asking an audience member for a camera to record the moment."

In 2011, Perry received an honorary doctorate from Illinois State University in recognition of his extraordinary contributions to the field of theatre.