Somewhere along the way, Michael Bolton picked up a reputation for being a very serious guy. But after donning a tri-cornered hat and a lot of eyeliner to honor Captain Jack Sparrow in a 2011 SNL skit, he suddenly became the funniest guy in music.

“I wasn’t so sure about it at first,” Bolton told “But it’s so extremely different than what anybody expected of me, except anybody who really knew me.

The romantic crooner was so happy that people finally got a chance to see the real Michael Bolton, he decided to start his memoir, The Soul Of It All, with the tale of how the video for “Jack Sparrow” actually came to be.

Some may wonder why Bolton would start his book with something that happened so recently, but he said that was exactly the reason why he chose to begin that way.

“I think that probably starts with a kind of contemporary relevance,” he explained. “What does it mean to people who are already fans of mine? They get a kick out of it because their kids are telling them about it.”

Even Andy Samberg, who made the viral clip with his fellow Lonely Island bandmates Jorma Taccone and Akiva Schaffer, let Bolton know on their first meeting that his mom was the most excited about them recording together.

The video may only be a little over three minutes long, but it took the guys over eight months to make. Bolton says the original idea for the clip, a filthy take on the Ten Commandments, was just too much for him so “Jack Sparrow” was the perfect middle ground.

Bolton and the guys from The Lonely Island, who he lovingly calls “the three-headed monster,” filmed the video in Brighton Beach, Brooklyn. He didn’t see his Jack Sparrow costume until the day of the shoot and still has some qualms with it.

“I didn’t realize it would take two hours to get the mascara off,” he said. “I’m not sure if Johnny Depp uses the same kind of stuff.”

Over the course of the two-day, 17-hour shoot, Bolton also dressed up as Forrest Gump, Tony Montana from Scarface and Erin Brockovich, something he won’t soon do again.

“Most traumatic part was seeing myself dressed in drag,” he joked. “That was like a traumatic, I need therapy moment.”

It was so traumatizing, the guys even chose to cut a scene in which Bolton, as Brockovich, breastfeeds a baby doll. “I don’t really know why they cut it,” Bolton said. 

Without the deleted scene, the video managed to became the third most watched video of 2011. Even now, two years later, Bolton still gets high-fives from teenagers for the clip.

At this point, he’s more surprised if someone tells him they haven’t seen the video. But once the person gets a chance to check it out, the response always seems to be the same.

“The next thing I get is a text or an email from them like ‘Oh My God!’ or ‘LOL.’”

To read more about the infamous “Jack Sparrow,” pick up Bolton’s book, The Soul Of It All, out now.

Shannon Carlin, Radio. com


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