“I would like to be remembered as a man who had a wonderful time living life, a man who had good friends, fine family, and I don’t think I could ask for anything more than that,” once said one of the most iconic entertainers of the 20th century, Frank Sinatra. The legendary crooner shared this heartfelt wish during his lifetime, reflecting on how he hoped to be remembered long after he was gone.
Known around the world as “The Chairman of the Board,” Sinatra built a legacy as a charismatic showman with a fiercely loyal inner circle — a reputation that, in today’s culture, mirrors the aura of UFC superstar Conor McGregor. It’s been 27 years since the world lost “Ol’ Blue Eyes,” but his legacy remains very much alive, particularly the old-school values he championed, such as loyalty, class, and respect.
A recent episode of The Joe Rogan Experience podcast (#2330) spotlighted that legacy; Joe Rogan interviewed U2 frontman and Irish songwriter Paul Hewson, better known as Bono. During their conversation, Bono reflected on his own personal memories with Frank Sinatra. The two famously collaborated on a duet in 1993, performing “I’ve Got You Under My Skin” for Sinatra’s Duets album.
Looking back on their time together, Bono shared a touching anecdote that showed just how generous and thoughtful Frank Sinatra truly was. Bono revealed,
“If we’re going to talk about singers, you have to talk about Sinatra. I had extraordinary times with him. He used to send—he sent me gifts every year. I have a gold and sapphire Cartier watch he sent me. Just… every year, he would send stuff. And because we did a duet together on his first Duets album—I’ve Got You Under My Skin.”
BOSTON, MA – JANUARY 20: Joe Rogan is seen in the commentary booth during the UFC 220 event at TD Garden on January 20, 2018 in Boston, Massachusetts. (Photo by Jeff Bottari/Zuffa LLC/Zuffa LLC via Getty Images)
Sinatra’s “Duets” album featured this famous duet between Frank Sinatra and Bono. Interestingly, the original song was first released back in March the legendary Cole Porter wrote 1956. Without a doubt, Sinatra’s larger-than-life personality perfectly matched the grandeur of his music career.
Over the years, he went on to collect numerous accolades—from Grammys to Golden Globes, and even received prestigious honors such as the Presidential Award. Ultimately, Sinatra and Bono’s friendship and collaboration remain one of the most remarkable relationships in the entertainment world.
Bono revealed an unspoken truth about Frank Sinatra
While Bono and Frank Sinatra collaborated on only one track, their bond went far beyond the music — a rare friendship that still resonates in the entertainment world today. Bono has often reflected on his final encounters with Sinatra before the legendary crooner passed away. In 2022, appearing on The Graham Norton Show to promote his memoir Surrender, Bono recounted his first meeting with “The Chairman of the Board.” He recalled how Sinatra was initially wary of his appearance, but ultimately warmed to him.
“He was a tough guy, and I’m attracted to tough guys,” Bono said. “He told me, ‘You are the only man with an earring I am going to like.’” Bono also shared that he and U2 had written a song specifically for Sinatra titled “Two Shots of Happy, One Shot of Sad,” though sadly, Frank Sinatra passed away before he had the chance to record it. In a separate interview with Rolling Stone magazine years earlier, Bono paid tribute to the late icon, saying, “Frank never did like rock and roll,” and fondly referred to the Fly Me to the Moon legend as “the boss of bosses.”
Frank Sinatra died in May 1998 at 82, closing a significant chapter. His long career in music, film, and iconic performances secured his spot in entertainment history. Sinatra defined a unique era, going beyond just being a singer. Which parts of this legendary entertainer’s legacy stand out to you the most? Leave your comments below.
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