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Life Behind the Fame

George Clooney Recalls Early Days In Hollywood – When He Met Tony Bennett And Got Yelled At By Frank Sinatra

by Ruth A

Published November 2, 2025

George Clooney is revisiting his early Hollywood memories—long before his rise to fame. The 64-year-old actor shared heartfelt and funny reflections during an exclusive chat with People at the Los Angeles premiere of his new film, Jay Kelly, during the AFI Fest.

Back then, George Clooney was just starting out and worked as his Aunt Rosemary Clooney’s driver. The experience gave him a front-row seat to show business and taught him lessons about success, failure, and humility that he still carries today.

Related:

  1. Tony Bennett’s Greatest Duets From Judy Garland To Frank Sinatra
  2. Lady Gaga Recalls How The Late Tony Bennett “Saved My Life”

George Clooney Reflects On Lessons From His Aunt Rosemary

George Clooney Was So Badly Stricken With COVID He Was Forced To Direct New Film From Bed
London, UK. George Clooney at the
Catch 22—TV Series premiere at the Vue Westfield, Westfield Shopping Centre, Shepherd’s Bush, London, 15th May 2019.
Ref: LMK73-S2430-169519
Keith Mayhew/Landmark Media
WWW.LMKMEDIA.COM

Before landing his breakout roles, George Clooney spent a year driving his famous aunt and other stars, including Tony Bennett. “I got to drive [her] and Tony Bennett and all of these really wonderful singers around for a year,” he said. Those early travels filled with music and laughter gave him a glimpse into the heart of Hollywood.

Rosemary Clooney’s dresses in White Christmas are INCREDIBLE. Every single one. Absolutely stunning: nicole/X

The Ocean’s 11 star said being around such icons helped him learn how to handle fame. “I got a really good life lesson in success and failure,” George Clooney shared. He added that he felt lucky to understand that balance early in his career.

George Clooney Shares His Frank Sinatra Story And Staying Grounded

FRANCIS ALBERT SINATRA DOES HIS THING, Frank Sinatra, (aired November 25, 1968), 1968. ph: Martin Mills / TV Guide / courtesy Everett Collection

George Clooney also recalled an unforgettable moment with Frank Sinatra. “I remember he was mad at me once because I led this boycott about some press freedoms,” he said with a grin. Sinatra called him directly, upset about helicopters over his home. “He said, ‘It’s not working, what you’re doing!’ But he was great. I got yelled at by Frank Sinatra!”

ALWAYS AT THE CARLYLE, George Clooney, 2018. © Good Deed Entertainment Courtesy Everett Collection

Today, George Clooney says he stays grounded through lifelong friendships. “Most of my friends—we’ve been friends for 40 years. I slept on their couch when I was broke,” he shared. Those same friends remind him of who he was before fame, keeping him balanced no matter how bright the spotlight shines.

Next up: Wolfgang Van Halen Speaks Out About Nepotism And Forging His Own Legacy

Previous article: Debbie Harry Finally Explains One-Word Lyric That Got Blondie ‘Banned’
Next Post: ‘Dukes Of Hazzard’ Stars Send Love And Prayers To Catherine Bach Following Hospitalization

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