George Clooney reflected on his yearslong friendship with the late Matthew Perry in an interview with Deadline published on Tuesday (December 19th). The Ocean’s 11 actor said he was “really close” with the cast of Friends while he starred on E.R. because they filmed their respective shows on the same lot.

“I knew Matt when he was 16 years old. We used to play paddle tennis together,” Clooney said. “He’s about 10 years younger than me. And he was a great, funny, funny, funny kid.”

The Gravity actor recalled Perry telling him, Richard Kind, and Grant Heslov, “’I just want to get on a sitcom, man. I just want to get on a regular sitcom, and I would be the happiest man on earth.’” Despite finally achieving this goal, the Fools Rush In actor “wasn’t happy,” according to Clooney.

“It didn’t bring him joy or happiness or peace. And watching that go on on the lot — we were at Warner Brothers, we were there right next to each other — it was hard to watch because we didn’t know what was going through him,” the Perfect Storm actor added. “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.”