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Exclusive: Michael Bolton opens up about the challenges he faced as an aspiring singer

The singer has had a career spanning nearly five decades

michael bolton
Sharnaz Shahid
Deputy Online Editor
March 1, 2019
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Michael Bolton is one of America's biggest music sensations. The 66-year-old has sold more than 75 million records over the course of a career spanning nearly five decades, with big hits including When a Man Loves a Woman and Missing You Now. But in a candid interview with HELLO! in March 2018, Michael confessed that there were several moments in his life when he wanted to give up - particularly at the very start of his singing career. "There were a lot of experiences that were promising at the start," he shared. "You get to a point where you don't want to believe that it's finally happening and then be disappointed and heartbroken. Heartbroken and flat-broken, that's the title of somebody's album there. But this happened over and over again."

Michael Bolton archive© Photo: Getty Images

Michael Bolton is famous for singing When a Man Loves a Woman

Michael, who has worked with the likes of Ray Charles and Pavarotti, admitted that he was so focused on succeeding in the music industry that there was never a "plan b" option. He explained: "I could have given up so many times. I describe it as a long walk out into the desert, with occasional cups of water being delivered by an executive saying 'you've got what it takes, come work with us, do an album or two and let's give it a try'. So I had encouragement from people in the industry, who I believed knew what they were talking about."


The younger generation will perhaps know Michael for starring alongside American comedy troupe The Lonely Island in the Saturday Night Live digital short Jack Sparrow. The video immediately went viral in 2011 and has now had over 180 million views. With a sequel in the works, the American crooner opened up about the moment he was asked to collaborate. "I was a big fan of the Lonely Island guys so I wanted to do something with them," he said. "The first idea they pitched me, I was sitting at table in Los Angeles looking at all three of them and I felt like I knew them.

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"They felt they knew me because we had seen each other in the business. I said I really wanted to do this video, but the language was so bad that a lot of my fans wouldn't get it, they might get offended." Explaining how he toned down the language, Michael continued: "They said yes [to tweaking], but I thought they were just being nice to me, they're so busy. Then they sent the latest version, and I'm reading it and it's still disgusting, vile. Funny, but… so my instincts were to protect myself and my fan base first, and try to make this happened."

The crooner has had a career spanning nearly five decades

But working with the guys - Andy Samberg, Jorma Taccone and Akiva Schaffer - was certainly an unforgettable experience. "It was so traumatising when I saw my reflection in that camera. People were laughing their [explicit] off - the crew were losing it at the end of a take. Just cracking up," added Michael. "No one was looking at their watch, nobody wanted to stop working. They're gracious people to work with, they're intense and focused - like a three headed monster but a genius one. It was so much fun but I was terrified when it aired. I was at the set and found a corner I could hide in, in case people didn't laugh at the funny parts."

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