George Clooney reflected on a surprisingly vivid memory from the beginning of his career: an encounter in which Frank Sinatra scolded him.

Speaking at the Los Angeles premiere of Jay Kelly on Thursday, Oct. 23, Clooney described how, while trying to establish himself in Hollywood, he wound up rubbing shoulders with several legendary performers, including Sinatra and Tony Bennett.

He explained that early on he worked as his Aunt Rosemary’s driver when she toured. Having grown up in Kentucky, Clooney said he moved to Los Angeles to pursue opportunities and found himself chauffeuring his aunt and renowned singers for about a year — an experience that taught him hard-earned lessons about both success and failure.

“I got a really good life lesson in success and failure, and handling it,” Clooney said.

One memorable moment involved Sinatra reacting to a press boycott Clooney helped organize. According to Clooney, people had begun speculating that Sinatra was ill after helicopters hovered near his home, and Sinatra phoned to express his frustration.

“It’s not working what you’re doing!” Sinatra told him, Clooney recalled.

Despite the rebuke, Clooney spoke warmly of the encounter. “He was great,” he said, laughing at the memory. “I got yelled at by Frank Sinatra!”

Clooney — who later won Academy Awards as both an actor and a producer — said those early experiences shaped his perspective. Longstanding friendships, he noted, kept him grounded: friends who stood by him when he was struggling and who remind him not to take praise too seriously.

“Most of my friends — we’ve known each other for decades. I slept on their couches when I was broke. They’re the first ones to remind you when people are giving you too much credit,” he added.

Reporting adapted from an interview published by People.

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