The second Michael Bolton heard about Gasparilla — the annual Tampa bacchanal that will bring hundreds of thousands of pirates to Bayshore Boulevard on Jan. 25 — you could hear the intrigue in his deep, dusty rasp.
“I wasn’t aware of it," Bolton said by phone from his home state of Connecticut. "But while you were talking, I was thinking: Is that something that Jack Sparrow shows up for?”
Now, don’t go getting your hopes mizzen-high. Bolton’s a busy man these days — busier than he has been in a while, actually, and the whole Jack Sparrow thing is a big reason why — and he probably won’t show up in costume at the pirate parade.
Even though he has that day off.
And even though it would go super viral.
And even though he might sing a certain new-school pirate chanty as a nod to Gasparilla when he performs Jan. 24 at the Seminole Hard Rock Hotel and Casino — which just happens to be the parade’s title sponsor.
“It depends on how loud it gets in the audience,” said Bolton, 66. “Inevitably, we get enough requests for it that we throw in a couple of verses and choruses of Jack Sparrow. And at the end of it, you see a lot of people really happy. And then from the stage, you see a bunch of other people with their jaws dropped, trying to figure out, What just happened?”
Let us ring in Gasparilla 2020 with the tale of Jack Sparrow, a novelty song that turned Bolton from a joke into the jester of Tortuga — and a guy a whole new generation suddenly wants a piece of.
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The year was 2011, and the best things on Saturday Night Live were the digital shorts created by musical comedy trio the Lonely Island. Andy Samberg, Akiva Schaffer and Jorma Taccone had scored huge viral hits with Lazy Sunday, D--- in a Box and I’m On a Boat, and had an idea for a song that veered from verses about getting crunk in the club into a chorus about Disney’s Pirates of the Caribbean franchise.
The man they wanted for the hook: Michael Bolton.
On one level, this made sense. Bolton has sold more than 65 million records and won two Grammys in the early ’90s. His beefcake chin, pulp-novel hair and belt-it-out pipes turned anguished ballads like How Can We Be Lovers, How Am I Supposed to Live Without You and Said I Loved You ... But I Lied into multiplatinum smashes.
On the other, he was ... well, Michael Bolton. He’d worked with Bob Dylan, Luciano Pavarotti and Ray Charles, but was so critically reviled that his name had become shorthand for soulless, meaningless mom-pop. His name was a running joke in the 1999 comedy Office Space, and he hadn’t sniffed the Top 40 in more than a decade. Young artists were not exactly beating down his door.
Bolton could be a funny guy, and he was a fan of the Lonely Island. But in his heyday as a critical punching bag, he felt he couldn’t let that side of himself show.
“I had to work really hard to establish myself as an artist, and I probably took myself too seriously,” he said. “It didn’t stifle my sense of humor as much as I felt like I was guarded. When I look at some of my old interviews, I read something, and I think: That’s me being really guarded, and trying to direct and control the narrative in a way that doesn’t look like I’m having fun.”
He was wary with the Lonely Island, too. The first draft of the song was “really offensive — funny to me, but it would have been offensive to a lot of people.” The group revised it several times per Bolton’s concerns, including how he’d be portrayed on screen while sing-quoting an X-rated line from Scarface.
“There had to be some boundaries, because what I didn’t want was my audience to be suddenly feeling like I was turning my back on them, traveling down this road,” he said.
He spent about four hours recording his parts while on tour in Atlanta, then flew to New York, where the SNL costume and makeup crew transformed him into a makeshift Johnny Depp, belting out lyrics about Davy Jones and giant squid in classic Michael Bolton fashion.
He watched the show from a dark, quiet corner of the SNL studios, holding his breath until he heard the audience laughing at all the right parts. It killed. On his way out, he bumped into a fellow Nutmeg Stater, John Mayer.
“You’re going to see something happen that you’ve never seen,” Mayer told him. “There’s going to be an audience that doesn’t even know your music who is now going to be completely aware of you.”
“I hope it’s going to be good,” Bolton said.
“It’s going to be great,” Mayer said.
Sure enough, the next morning, Bolton’s daughter showed the singer how fast the video had taken off. (It now has more than 200 million views on YouTube.) Real pop stars were tweeting it out. And just like that, Bolton said, “I got permission to have fun.”
After Jack Sparrow, Bolton became a genuine comedic presence, often playing “some sort of exaggerated version of myself.” He appeared on Two and a Half Men and Fresh Off the Boat, as well as the Lonely Island movie Popstar: Never Stop Never Stopping. He sang Jack Sparrow at the Emmys and was nominated for one for an episode of the digital series Honest Trailers. He started developing his own film and TV projects, including Netflix’s Michael Bolton’s Big Sexy Valentine’s Day Special, co-directed by Schaffer.
The best part: Many of his serious, lifelong fans came along for the ride.
“They have every album, every CD, every cassette tape. And I can joke around with them now," he said. "I feel like the pressure is off in a way that I can be as funny as I want to be, and push my audience as far as they’re willing to go.”
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Here’s the other thing about Jack Sparrow: It changed how a generation saw Bolton as a singer.
When he called from Connecticut, he was about to catch a flight to Los Angeles to work on a new album he hopes to release this year. It’s his first album of mostly original material since 2009′s One World One Love. And he’s working with a much younger group of writers, producers and artists who are bringing him ideas he hasn’t really played with before.
“What’s interesting is they want part of what’s classic,” he said. “I expected it to be difficult to work with young writers, because music is changing so quickly and has changed so much. I’ve found that they actually want to be part of some music that’s going to be around as many years as my music has been around.”
He calls his new songs “the most exciting ones I’ve written,” saying it “sounds like it could be a greatest hits album, but with brand new songs that feel fresh.”
Would that have happened without Jack Sparrow? Maybe not. The experience encouraged him to take risks, open himself to new influences and listen to unlikely collaborators eager to engage with an under-appreciated legend.
“There will always be amazing voices coming around, staggering voices, but they won’t have a career if they don’t have the right songs,” he said. “That’s a key element to success in any arena, every genre of music: Music you’ve never heard before feels good.”
Spoken like ol’ Captain Jack himself. Don’t be surprised if Bolton sticks around for Gasparilla after all.
8 p.m. Jan. 24. $70 and up. Seminole Hard Rock Hotel and Casino, 5223 Orient Road, Tampa. (813) 387–9838. seminolehardrocktampa.com.