George Clooney and Matthew Perry were friends for decades. The two, being a part of two of the most iconic ‘90s series of all time, met when they were young, and spents lots of time together thanks to their work on TV. In a new interview, Clooney revealed that Perry had acquired fame and money but that that still didn’t make him happy.

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Clooney is currently promoting his film “The Boys In The Boat” and opened up about his relationship with Perry. “ We were side by side on the soundstage,” said Clooney to Deadline, with both of their shows, “ER” and “Friends,” premiering in the same year. “I knew Matt when he was 16 years old. We used to play paddle tennis together. He’s about 10 years younger than me. And he was a great, funny, funny, funny kid,” he said.

Clooney revealed that Perry had been longing to star in a sitcom, claiming that a gig like that would make him happy. “And he got on probably one of the best ever. He wasn’t happy. It didn’t bring him joy or happiness or peace,” he said. “We just knew that he wasn’t happy and I had no idea he was doing what, 12 Vicodin a day and all the stuff he talked about, all that heartbreaking stuff. And it also just tells you that success and money and all those things, it doesn’t just automatically bring you happiness. You have to be happy with yourself and your life.”

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Matthew Perry’s death

Matthew Perry was found dead in his home in Los Angeles on October 28th. He was 54.

He struggled with addiction over the course of his life, and was open about his struggles, publishing a memoir called “Friends, Lovers, and the Big Terrible Thing” in 2022. In an interview with PEOPLE, Perry discussed his pride over his sobriety and his desire to help others facing similar problems in life. “I had to wait until I was pretty safely sober—and away from the active disease of alcoholism and addiction—to write it all down. I was pretty certain that it would help people if I did,” he said at the time.