George Clooney Recalls Memorable Encounter With Frank Sinatra

By Zoe Papadakis | Tuesday, 28 October 2025 01:31 PM EDT

George Clooney has shared a cherished memory from his Hollywood career, detailing an instance where he was publicly reprimanded by Frank Sinatra. Speaking to People at the Los Angeles premiere of his new film “Jay Kelly” during AFI Fest on Oct. 23, the 64-year-old actor reflected on the moment with nostalgia.

“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], and he called me going, ‘It’s not working what you’re doing!'” Clooney said. “But he was great. I got yelled at by Frank Sinatra!”

Clooney’s connection to Sinatra dates back to his early career in the entertainment industry, when he worked as a driver for his aunt, singer Rosemary Clooney, who performed alongside many of Sinatra’s contemporaries. The Oscar winner described these experiences as offering a firsthand look at show business and the challenges of fame.

“I remember being on the road […] I was my Aunt Rosemary’s driver when she was singing,” he said. “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,” Clooney added. “And I got to drive [her] and Tony Bennett and all of these really wonderful singers around for a year.”

He emphasized that the experience provided an early understanding of the complexities of public life. “I got a really good life lesson in success and failure and handling it. And I always remember that […] I felt very lucky that I got that lesson early in time,” he said.

Reflecting on his enduring friendships, Clooney noted how his close circle has helped him remain grounded despite decades in the spotlight. “Well, I mean, most of my friends […] we’ve been friends for 40 years. I slept on their couch when I was broke.”

“And so, they’re always around when things and people are giving you too much credit,” he said. “They’re the first people to remind you that they’re full of crap. That’s always helpful.”

Earlier this month, Clooney confirmed that “Ocean’s 14,” the next installment in the Ocean’s franchise, is moving forward at Warner Bros. with plans to begin filming in 2026. “Yeah, we just got it. We just got the budget approved at Warner Brothers, and we’re trying to set up,” he told E! News. “It’s just scheduling, so it’s just setting a start date for us, probably starting about nine or 10 months.”

The new film would reunite Clooney with Brad Pitt and Matt Damon, continuing the series that began with “Ocean’s 11” in 2001—a remake of the 1960 classic led by Sinatra and The Rat Pack.