Matthew Perry was once one of television’s most beloved actors. For ten years, from 1994 to 2004, he played the unforgettably sarcastic Chandler Bing on the hit NBC sitcom Friends, a role that snagged him an Emmy nomination for Outstanding Lead Actor in a Comedy Series in 2002. He later followed up on his small screen success with the shows Studio 60 on the Sunset Strip, Mr. Sunshine, and Go On — not to mention films like The Whole Nine Yards and Serving Sara. But while Perry’s pockets were likely lined with lots of cash, his private life was secretly falling apart.

From an addiction to prescription pills and several trips to rehab to health issues and surprising scandals, Perry’s Hollywood life hasn’t been all red carpets and applause. In fact, his real-life story has been downright tragic. Keep reading to learn all about the actor’s off-screen troubles that have, unfortunately, spanned decades.