From Driver to Dialogue: Clooney’s Early Hollywood Experiences

Before achieving international stardom, Clooney’s path to success involved a more grounded role: driving for his aunt, the celebrated singer Rosemary Clooney. He recounted to People magazine how this experience provided invaluable lessons in both triumph and adversity. “I remember being on the road… I was my Aunt Rosemary’s driver when she was singing,” Clooney explained. “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 period allowed him to observe and learn from a constellation of musical icons, including Tony Bennett. “I got to drive [her] and Tony Bennett, and all of these really wonderful singers around for a year. I got a really good life lesson in success and failure, and handling it,” Clooney shared. It was within this vibrant atmosphere that he would eventually cross paths – and occasionally clash – with the formidable Frank Sinatra.

The Boycott and the Blast: A Clash of Ideals

The incident with Sinatra stemmed from a boycott Clooney spearheaded concerning press freedoms. The situation escalated when rumors of Sinatra’s ill health began circulating, attracting unwanted media attention, including helicopters hovering over his home. Sinatra, reportedly frustrated, directly contacted Clooney. “He called me going, ‘It’s not working what you’re doing!’” Clooney recalled. Despite the stern rebuke, Clooney held a respectful view of the icon. “He was great,” Clooney added, “I got yelled at by Frank Sinatra!”

Did You Know?: Frank Sinatra was known for his strong opinions and unwavering loyalty, often fiercely protecting his friends and colleagues from perceived slights.

Looking Ahead: ‘Ocean’s 14’ and a Return to Heist Thrills

Clooney’s career continues to flourish, with exciting projects on the horizon. He recently confirmed that Ocean’s 14 is likely to begin filming in 2026, potentially reuniting him with Brad Pitt and Matt Damon. The original Ocean’s 11 (2001), a remake of the 1960 classic starring Sinatra and the Rat Pack, remains a highlight of Clooney’s filmography, showcasing a masterful blend of charisma and cunning. The film’s success cemented his status as a leading man and demonstrated his ability to revitalize a beloved franchise.

Currently, Clooney is garnering praise for his performance in Jay Kelly, a comedy co-starring Adam Sandler. The film has received a four-star review from NME’s Matthew Turner, who described it as “easily one of the Hollywood heavyweight’s most enjoyable performances to date.” The film is scheduled for release on November 14th.

What do you think about Clooney’s story? Does it change your perception of either actor? Share your thoughts in the comments below!

Frequently Asked Questions About George Clooney and Frank Sinatra