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Skip to main content George Clooney arrives at the American Film Institute's 46th Life Achievement Award Gala Tribute to George Clooney on June 7, 2018 in Hollywood, Calif. Axelle/Bauer-Griffin/FilmMagic Trending on Billboard George Clooney is looking back at one of the more surreal moments from his early Hollywood days — getting personally scolded by the legendary Frank Sinatra. While attending the Los Angeles premiere of his new film Jay Kelly on Thursday (Oct. 23), the actor recalled his brushes with legendary artists like Sinatra and Tony Bennett during a time when he was trying to get a foothold in the industry. Thom Yorke Reveals Why Radiohead Haven't Toured Since 2018 Hailey Bieber Reveals If She Wants More Kids With Justin Bieber Carly Rae Jepsen and Cole M.G.N. Marry at New York's Chelsea Hotel Frank Sinatra George Clooney See latest videos, charts and news “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.” At the time, Clooney found himself in close proximity to giants of American music, including Bennett, Sinatra and more. “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 of the more unexpected encounters came courtesy of Sinatra himself, who wasn’t thrilled with a press boycott Clooney was involved in. “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!’” Still, Clooney took the confrontation 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, said those formative experiences helped shape his approach to success — especially 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.” Get weekly rundowns straight to your inbox Want to know what everyone in the music business is talking about? Get in the know on Visit Billboard Pro for music business news Billboard is a part of Penske Media Corporation. © 2025 Billboard Media, LLC. All Rights Reserved. Powered by WordPress.com VIP optional screen reader Manage Account Billboard Hot 100™ Billboard 200™ Hits Of The World™ Songs Of The Summer Year-End Charts Decade-End Charts R&B/Hip-Hop Business News Record Labels View All Pro Songwriters & Producers Artist Index Royalty Calculator Market Watch Industry Events Calendar Billboard Español Cultura y Entretenimiento Crossword Puzzle GET ACCESS TODAY
