Michael Bolton recalls recording 'Jack Sparrow' with the Lonely Island 10 years ago: 'One of the best things I ever did'

·Editor in Chief, Yahoo Music
·6 min read

Michael Bolton is connecting with a whole new audience these days as the crooning co-host of Celebrity Dating Game, but it was 10 years ago that the balladeer experienced his first hipster career renaissance, when he teamed with the Lonely Island for the SNL Digital Short “Jack Sparrow.”

Bolton, a self-described “ginormous fan” of the Lonely Island, absolutely lights up when asked about the 2011 collaboration during a Yahoo Entertainment interview, describing it as “one of the “most enjoyable, greatest experiences” of his career. “You just reminded me how much fun I really had making that,” he says with a smile.

Bolton admits that when Andy Samberg and company reached out to him with the concept — in which Pirates of the Caribbean superfan Bolton belts a “big, sexy hook” about Jack Sparrow that totally jars with the song’s overall clubby, hip-hop vibe — he was worried that “some of the lyrics were a little bit raunchy” and inappropriate for his conservative fanbase. But the Lonely Island guys were so eager to have him sign on that they agreed to change the lyrics. “I read [the revised version] and it started to feel great, until all of a sudden it got to a point that was even darker than the first one — like they kind of started going in the other direction!” Bolton chuckles. Finally they compromised, and “the next thing I knew, I was going in to sing.”

When the Lonely Island played the track for the Saturday Night Live brass, Bolton says “they went crazy for it.” So, now it was time to film the video short, which Bolton says was such a fun process that he never wanted the two-day shoot to end. “I wasn't ready to leave by the end of the second day, which I think was the 12-hour day,” he laughs. “I was, like, not wanting to stop, because it just was getting better and better. And they were getting constant feedback from the executives at Saturday Night Live that they were flipping out over it. … I'm so glad that I was all-in and trying stuff. You shouldn't limit everything to what your preconceived notion is. With [the Lonely Island], it's going to be funny, if not a hundred percent of the time, then 92.4 percent of the time. It's going to be funny, and you're going to be glad you did it.”

The “Jack Sparrow” short parodied other movies besides the Pirates franchise, and Bolton quips that his riskiest scene, when he dressed up in Erin Brockovich drag, was “a little bit traumatic for me, because I saw what I looked like in the camera lens! I almost had a meltdown, as if I was going to need therapy immediately! But it turns out that the funniest part during the Erin Brockovich filming was left out, and that's where I'm holding the law books and holding the baby, and next thing you know, I'm breastfeeding the baby. That didn't make it into the final cut.”

However, Bolton was particularly proud of the video’s Scarface spoof — so much so that when he later ran into Al Pacino at the Polo Lounge in Los Angeles, he recalls, “[Pacino] looked up at me and he smiled, and I was thinking, ‘Should I walk over there and talk to him?’ … I could tell he approved.”

Michael Bolton performs with the Lonely Island at the 2011 Emmy Awards. (Photo: Reuters /Mario Anzuoni)
Michael Bolton performs with the Lonely Island at the 2011 Emmy Awards. (Photo: Reuters /Mario Anzuoni)

Bolton had loved doing the video shoot, but he was still nervous when he flew to New York to be in the SNL studio when “Jack Sparrow” aired for the first time. “I was looking for the darkest corner in the room, just in case it didn't go over, and I found a place. I found the single darkest place in any building at any network,” he recalls. “But people were chuckling and laughing at the right places. And then John Mayer came over to me at the afterparty [and said], ‘Tomorrow you're going to see something you've never seen before. It's going to be crazy.’ I said, “Well, what do you mean? It’s good?’ He said, ‘You're going to have so many fans that don't even know your music. … This is a different world.’ And I said, ‘Well, I hope you're right, man. Thank you.’”

Bolton still didn’t grasp what an instant sensation “Jack Sparrow” was — and how much it would alter the trajectory of his career — until the next morning, when he found his daughter sitting at the kitchen table, “scrolling through thousands of comments, including Justin Bieber, who said, ‘Bolton is a beast, you gotta check this out.’ And my daughter looked up at me and said, ‘You're not going to believe what's going on!’ And I said, ‘Is it good? Is it all good?’ And next thing I knew, I was having a celebration drink with the Lonely Island… we were celebrating arriving at 50 million views. And then it went to a hundred, and then 200.” As of September 2021, “Jack Sparrow” has racked up 220 million views on YouTube alone.

“It manifests quickly, because I was at the airport and these kids were staring at me; there were like 14-year-olds, 16-year-olds, and I could tell it was all about ‘Jack Sparrow,’” Bolton laughs. “So now I've got ‘When a Man Loves a Woman’ — when I walk through security at the airports, the guys sing ‘When a Man Loves a Woman’ to me. When I go through and there are women at the security area, they sing ‘How Am I Supposed to Live Without You.’ And when it's kids, it's all ‘Jack Sparrow.’”

Michael Bolton performs with the Lonely Island at Clusterfest in 2018. (Photo: Jeff Kravitz/FilmMagic)
Michael Bolton performs with the Lonely Island at Clusterfest in 2018. (Photo: Jeff Kravitz/FilmMagic)

Bolton so enjoyed the SNL experience that a decade later he’s still eager to do more comedy, revealing, “I've got a song that I think would be perfect for the Lonely Island guys that I want to do. It would be fun to do a whole album with them. It's been incredible, and it has opened this much bigger, universal door into projects. I think when people see that you'll have fun — and you want to have fun even if it's self-deprecating — it works. Basically, it was one of the best things I ever did. I call it the gift that keeps on giving.”

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— Video produced by Jen Kucsak, edited by Jason Fitzpatrick