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

Speaking at the Los Angeles premiere of his new film Jay Kelly on Thursday (Oct. 23), Clooney recounted his experiences with music legends like Sinatra and Tony Bennett during a time when he was trying to make a name for himself in Hollywood.

“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 had the rare opportunity to be around some of America’s most celebrated singers, 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 memorable encounter involved Sinatra, who reportedly was unhappy 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 tense moment, Clooney said he took it in stride. “He was great,” he added. “I got yelled at by Frank Sinatra!”

Clooney, who would go on to win Oscars for both acting and producing, credited these early experiences with shaping his perspective on success and the importance of staying 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.”