At the Los Angeles premiere of his new film Jay Kelly on October 23, George Clooney shared a memorable story from early in his career about a direct confrontation with musical legend Frank Sinatra. Clooney recounted how his experiences with iconic performers like Sinatra and Tony Bennett shaped his understanding of success and failure in Hollywood.
During that period, Clooney worked closely with various renowned artists while trying to establish himself. He served as a driver for his Aunt Rosemary, who was a singer, which brought him into contact with many legendary figures in American entertainment.
Early Career Lessons from Legendary Musicians
Clooney explained,
“I remember being on the road […] I was my Aunt Rosemary’s driver when she was singing,”
describing how this role exposed him to the world of famous singers.
“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.”
This opportunity allowed him not only to support a family member but also to learn from the lives and careers of prominent musicians.
He went on to elaborate on the lessons learned through this experience:
“I got to drive [her] and Tony Bennett, and all of these really wonderful singers around for a year,”
Clooney said.
“I got a really good life lesson in success and failure, and handling it.”
These encounters gave him valuable insight into managing both triumphs and setbacks in the entertainment business.
Frank Sinatra’s Displeasure Over a Press Boycott
One of the more striking moments came when Frank Sinatra personally expressed frustration with Clooney over a press boycott Clooney was leading. Clooney recalled,
“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].”
Sinatra’s call was direct:
“And he called me going, ‘It’s not working what you’re doing!’”
Despite being scolded by one of the world’s most famous entertainers, Clooney took the encounter in stride and spoke positively about Sinatra’s character afterward: He was great, he noted.
“I got yelled at by Frank Sinatra!”
Friendships That Grounded Clooney Through Success
Looking back on those early experiences, Clooney emphasized how important close friendships have remained throughout his life and career. He said,
“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,”
highlighting the value of loyalty and honesty in the often intense world of fame.
He added,
“They’re the first people to remind you that they’re full of crap,”
underscoring how those relationships help maintain humility despite public success. Clooney’s reflections reveal how his formative years and interactions with entertainers like Frank Sinatra contributed to the grounded perspective he carries today.
