Michael Bolton's SNL Jack Sparrow Parody Was So Vulgar And 'Undoable' At First

During The Lonely Island's time on "Saturday Night Live," fans eagerly awaited new Digital Shorts from the trio — especially after "Lazy Sunday" went wildly viral in late 2005. From there, celebrity guests started popping up alongside Andy Samberg, Jorma Taccone, and Akiva Schaffer whenever they saw fit to make a new short. Natalie Portman lampooned her image with a deeply offensive rap song. Justin Timberlake marked his first collaboration with The Lonely Island with "D*** in a Box." And then, of course, crooner Michael Bolton teamed up with the three comedians for "Jack Sparrow."

Bolton revisited the now-classic sketch in an interview with Vulture, where he admitted that, at first, the material was so obscene that he had to ask for some serious rewrites. Asked how the Lonely Island guys approached him, Bolton said, "A phone call came in, and they said they wanted to have a meeting ... I soon found myself in a conference room at a hotel in Los Angeles — my manager and me on one side of the table, and Akiva, Jorma, and Andy sitting across from us." 

"So they pitched 'Jack Sparrow' to me," Bolton admitted. "The pitch was undoable. It was beyond vulgar." When Vulture pressed him on it, Bolton elaborated: "Whatever you're thinking, it was more vulgar than that. Even though I understood what was funny about it, I thought I could be insulting the first 10 rows of my live audience if I said 'yes.' I was playing at the Vatican, you know what I mean?"

As Michael Bolton recalled, Andy Samberg, Jorma Taccone, and Akiva Schaffer understood his concerns and said they could try and make it work. "So the guys said, 'We've had other people who worked with us who had concerns like this, and we've worked it out,'" Bolton told Vulture. "'We can tweak it. We'll send you different ideas, and hopefully we can do something that will work for both of us' ... but within a week or so, I got the tweaked treatment and they made it even worse. They just went to some dark places."

Luckily, it all got ironed out, as Bolton revealed: "They said, 'Okay, well, we'll go at it again.' At this point, I thought they were pulling me along. I didn't know how likely it was that we would be doing anything together. But they got back to me with another version a few months later that was heading in the right direction."

The finished sketch, while still vulgar at points, is ultimately pretty light-hearted. After the fictionalized version of Bolton tells the Lonely Island guys that he wrote them a "big, sexy hook" for their new song, it turns out that, after binging the "Pirates of the Caribbean" movies, the whole hook is about Jack Sparrow (Johnny Depp) and what a cool guy he is. (This doesn't really vibe with The Lonely Island's existing banger about being hot dudes in the club.) 

So what was the exact nature of the vulgarity that gave Michael Bolton pause before filming "Jack Sparrow"? Vulture asked, but the singer demurred: "I don't think it would have the same power in a different context," he said. "But I remember the intention quite clearly. They were basically testing the water to see what they could get me to do." When Andy Samberg emailed the singer to ask about what would apparently become the final draft, Bolton had one stipulation. For the scenes where Bolton switches from Jack Sparrow to Tony Montana — Al Pacino's reprehensible character from "Scarface" — he needed to be in character as Tony Montana, not playing himself.

How does Tony Montana even factor in? Well, within the sketch, the Lonely Island guys ask Bolton to cool it with the "Pirates of the Caribbean" references, so he switches movies — pivoting first to "Forrest Gump," then "Erin Brokovich," and finally to "Scarface." As Samberg puts it in the sketch, "Turns out Michael Bolton is a major cinephile."

Naturally, the "Scarface" section of the short has the most obscene content, including a line where Bolton (as Montana) screams, "This whole town's a p***y just waiting to get f***ed." So why was Bolton okay with that line? "It's a quote from 'Scarface,' and I said I'd only sing it dressed like Scarface himself," the star reiterated. "That was my condition."

Not only did the sketch turn out to be an excellent addition to the Lonely Island's collection of Digital Shorts, but Michael Bolton told Vulture that the sketch helped change his public image for the better ... in that he could push more comedic boundaries. 

For example, after the sketch aired, Bolton appeared on four episodes of the Chuck Lorre sitcom "Two and a Half Men" as himself. During one of his appearances on the series, Bolton enters and Robin (Mimi Rogers), mother to Ashton Kutcher's Walden, was originally supposed to say, "Oh, my. I've never had an adult-contemporary artist in my house before." According to Bolton, this line fell completely flat during rehearsal, so he approached the writers, who welcomed his input.

"I said, 'The adult-contemporary line sounded a bit flat when we rehearsed it. I'm wondering if you could tweak that line,'" Bolton remembered. "The next day, when [Rogers] was coming down the stairs during rehearsal, she saw me and said, 'Oh, my. I have a vibrator named after you.' Everyone in the place stopped and broke out into laughter." It's possible that Bolton might not have been comfortable with this joke before "Jack Sparrow," but clearly, doing such a silly sketch made him a little bolder — plus, he learned from the Lonely Island guys that his input was valuable.

Not only did Michael Bolton agree to the script that Jorma Taccone, Akiva Schaffer, and Andy Samberg ended up writing, but he clearly thought they were talented enough to keep collaborating with them. Amazingly, "Jack Sparrow" wasn't the last time the three would work together. Bolton returned to their Digital Shorts series by making a cameo in the 100th short, and he also made a cameo in the trio's 2016 feature film "Popstar: Never Stop Never Stopping," playing himself during the movie's grand musical finale. Then, in 2017, Bolton teamed up with The Lonely Island for the original Netflix special "Michael Bolton's Big, Sexy Valentine's Day Special," which was directed by Schaffer and comedian Scott Aukerman and featured a murderer's row of other celebrities.

"For me, everything they asked made perfect sense," Bolton said, remembering how he and the trio eventually crafted their short. "Since then, when Akiva or Jorma or Andy calls, it's like one of your best friends is on the phone, and there's nothing but love and respect and curiosity about what they're working on and how we're going to work together again." Here's hoping that, whatever The Lonely Island and Michael Bolton do going forward, they find more ways to collaborate.