George Clooney Recalls Being Scolded by Frank Sinatra During Early Hollywood Days

Hollywood star George Clooney reflected on one of the more surreal moments from his early career — being personally scolded by the legendary Frank Sinatra.

Speaking at the Los Angeles premiere of his new film Jay Kelly on Thursday (Oct. 23), Clooney shared memories of his encounters with iconic artists like Sinatra and Tony Bennett during a time when he was striving to establish himself in the industry.

“I remember being on the road […] I was my Aunt Rosemary’s driver when she was singing,” Clooney told People. “And I hadn’t known her much when I was young because I lived in Kentucky. She was the Hollywood aunt. So I came out to make a living and I was her driver.”

During that period, Clooney found himself in close proximity to some of American music’s greatest names, including Bennett and Sinatra.

“I got to drive [her] and Tony Bennett, and all of these really wonderful singers around for a year,” he said. “I got a really good life lesson in success and failure, and handling it.”

One particularly unexpected encounter involved Sinatra, who reportedly wasn’t pleased with a press boycott Clooney had led. “I remember he was mad at me once because I led this boycott about […] some press freedoms, and he called me because people thought he was sick and there were helicopters flying over his [home],” Clooney recalled. “And he called me going, ‘It’s not working what you’re doing!’”

Despite the confrontation, Clooney said he took it in stride. “He was great,” he added. “I got yelled at by Frank Sinatra!”

Clooney, who would later win Oscars for both acting and producing, said these formative experiences influenced his understanding of success, particularly the importance of remaining grounded.

“Most of my friends, we’ve been friends for 40 years. I slept on their couch when I was broke. And they’re always around when people are giving you too much credit,” he said. “They’re the first people to remind you that they’re full of crap.”