Matthew Perry Played A Cop On This Short-Lived '90s Sitcom Starring An '80s TV Icon

Before "Friends" made him a legend in his own right, Matthew Perry was helping '80s legend Valerie Bertinelli bust bad guys on "Sydney." In 1990, Perry joined the cast of the CBS sitcom as Billy Kells, a rookie cop who is fiercely protective of his private-eye sister, Sydney (Bertinelli). "Sydney" centered around the investigative adventures of the titular character and served as a starring vehicle for Bertinelli, who was then known for her portrayal of the teenaged Barbara Cooper in the '80s staple "One Day at a Time." 

Although "Sydney" aired only a single season on CBS, its swift cancellation was far from the end for either Bertinelli or Perry. Bertinelli would go on to score main roles in shows such as "Touched by an Angel" and "Hot in Cleveland," and Perry eventually changed the landscape of sitcom television as the wisecracking Chandler Bing on "Friends."

Perry's part on "Sydney" marked one of his first stints as a series regular on a television show. The actor's early career also saw him headline the sitcoms "Home Free" and "Boys Will Be Boys," both of which similarly fell victim to early cancellations. But his 1994 casting on "Friends" established him as a worldwide household name; his willingness to occasionally embrace vulnerability in his portrayal of Chandler consistently garnered praise from critics and audiences alike.

According to Matthew Perry, getting cast on "Sydney" led to some of the most fun he'd ever had. "I feel guilty getting paid for coming here every day," Perry confessed during a 1990 interview with Entertainment Tonight on the "Sydney" set. "I feel like a cop's going to come in and arrest us all for getting paid for doing this 'cause it's just so much fun." 

Perry's comments further revealed that the actor had been considering the possibilities of global fame well before his portrayal of Chandler Bing took his rising star into the stratosphere. He described, "People say, 'Don't you go crazy when somebody asks you for your autograph?' ... I love it. Maybe I'll get sick of it if it happens [all the time], but I don't picture myself having a big attitude about that."

By the time of Perry's death in 2023, he had become one of the most celebrated actors in sitcom history. His tenure on "Friends" and his advocacy for individuals struggling with addiction cemented a legacy that was recognized by many, including the "Friends" creators and Perry's co-stars. "I think about [fame] in a realistic way," Perry continued in the same interview with Entertainment Tonight, speculating on the future of his career in a twist of bittersweet dramatic irony. "I don't think I'm gonna walk down the street and people are gonna go, 'Whoa!'"