‘It Was Beyond Vulgar’: Michael Bolton Says That Original Pitch for Lonely Island ‘Jack Sparrow’ Sketch Would Have Gotten Him Kicked Out of the Vatican

When The Lonely Island teamed up with Michael Bolton to make one of their most iconic digital shorts in May 2011, they offered the pop-rock icon the most crude, upsetting and brand-tainting script he’d ever heard of — but he had heard of it.

In the late aughts to early 2010s, Akiva Schaffer, Andy Samberg and Jorma Taccone were as synonymous with sketch comedy music videos as Bolton was with adult contemporary music most beloved by Christian women in their 40s and regional grocery store chains choosing mood music for the frozen foods aisle. The Lonely Island was a one-of-a-kind viral hitmaker that had every middle-schooler with an internet connection memorizing the lyrics to “Jizz in My Pants” and “Dick in A Box” to the annoyance of their mothers who just wanted to unwind with a glass of chilled wine and their old tape of Time, Love & Tenderness. Bolton and The Lonely Island were both massive hits, just with an equally enormous generational divide between them.

When The Lonely Island reached out to the Grammy-winning singer about collaborating on a song for Saturday Night Live, he was ecstatic to get the call and hopped aboard — before quickly realizing that the Digital Short demigods had Shanghai’d him to make the most obscenely offensive single of his life. “The pitch was undoable. It was beyond vulgar,” Bolton said of the first draft of “Jack Sparrow” in an interview with Vulture about the viral hit. “Whatever you’re thinking, it was more vulgar than that.” Two dicks in a box???

“A phone call came in, and they said they wanted to have a meeting,” Bolton recalled of The Lonely Island’s approach to working with him. “I loved what they’d done, and I wanted to be a part of the list of artists who worked with them.” Once Bolton met the comics in the flesh, he found that the admiration between them was symmetrically mutual. “I said, ‘My daughters are so excited about me having this meeting with you guys,’” Bolton explained, “And they said, ‘Our moms are so excited about us having this meeting with you.’”

Bolton’s reaction to The Lonely Island’s first idea for the sketch was one of understanding abhorrence, as he recalled, “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?” Though Bolton was ready to cast off his seductive yet squeaky clean persona for the sake of comedy, he wasn’t ready to take it as far as The Lonely Island expected of him. “So the guys said, ‘We’ve had other people who worked with us who had concerns like this, and we’ve worked it out. We can tweak it. We’ll send you different ideas, and hopefully we can do something that will work for both of us. We don’t want anyone else.’”

Bolton wouldn’t reveal exactly what kind of objectionable material the original lyrics for the video contained, but he explained his very reasonable apprehension toward the project, saying, “With some of the language in the pitch, I felt like, I’d love to do this, but I have this audience that I’ve been fortunate enough to build through the years and they come to the shows to hear the greatest hits. Songs they had families to and grew up to. You have to understand why I can’t sing these lyrics. They said, ‘Okay, well, we’ll go at it again.’”

Eventually, Samberg sent Bolton a script that he found almost agreeable, but they had to make a compromise. Said Bolton of his reply, “I responded, ‘I read the newest treatment and I think I can do it. But I need to be in character when I do any lines as Al Pacino’s character from Scarface.’”

Almost immediately after the sketch aired on SNL, Bolton saw a youthful shift in his demographics as he found his young daughter on a laptop reading responses to “Jack Sparrow” from across the internet. “She started reading me quotes, and Justin Bieber wrote, ‘Michael Bolton is a beast, you’ve got to see this.’ How does he know who I am?” Bolton remembered, “It taught me something important: Have freakin’ fun.”

The Lonely Island knows that they, too, can have fun while appealing to a new audience — Bolton isn’t the only singer who knows how to give a special woman an unforgettable Mother’s Day.