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He went on to play Chazz Russell in the TV series Second Chance.
After 13 episodes, Second Chance became Boys Will Be Boys, with the plots refocused on the adventures of Chazz and his teenage friends.
In 2009, he starred in the film 17 Again playing the older Mike O'Donnell.
In 2008, Perry starred in the offbeat film Birds of America as Morrie Tanager, an uptight man who has to deal with his siblings. Perry portrayed Ryan King, a sportscaster who tries to move on after the death of his wife through the help of mandatory therapy sessions.
After Friends wrapped up, Perry made his directorial debut in an episode of the 4th season of the American comedy-drama Scrubs, in which he also guest starred as "Murray Marks", an operator of a small airport's traffic control team.
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.
His three appearances in that series (twice in the fourth season and once in the fifth) earned him two Emmy nominations for Outstanding Guest Actor in a Drama Series in 20.
Perry portrayed "a charismatic man" who enchanted onlookers by throwing his dog in the air.
The play transferred Off-Broadway to MCC Theater, which opened on June 5, 2017, with Jennifer Morrison.