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In the midst of his many continuing guest roles on TV, Perry was cast as a regular on the 1990 CBS sitcom Sydney, playing the younger brother of Valerie Bertinelli's title character.

Perry received a Golden Globe nomination as well as an Emmy nomination for his performance.

In 2006-2007, Perry appeared in Aaron Sorkin's drama Studio 60 on the Sunset Strip.

Perry appeared in films such as Fools Rush In (alongside father John Bennett Perry and Salma Hayek), Almost Heroes, Three to Tango, The Whole Nine Yards (alongside Bruce Willis) and its sequel The Whole Ten Yards, and Serving Sara.

While known primarily for his comic roles, Perry has carved out a career in drama as well, particularly in his portrayal of Associate White House Counsel Joe Quincy in Aaron Sorkin's The West Wing.

He lost 20 pounds (9.1 kg) in 2000 due to pancreatitis.

He was filming Serving Sara in Texas when he suffered severe stomach pains, and flew to Los Angeles to check into Marina del Rey's Daniel Freeman Hospital.Perry completed a 28-day program in 1997 for a Vicodin addiction.His weight fluctuated drastically over the next few years and once dropped down to 145 pounds (66 kg).Perry landed his next TV starring role on the ABC sitcom Home Free, which aired only 11 episodes in the spring of 1993.By then, Perry was making his mark, and was instantly cast in a sitcom pilot titled LAX 2194.Perry played Matt Albie alongside Bradley Whitford's Danny Tripp, a writer-director duo brought in to help save a failing sketch show.

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