Great Moments in Comedy: The Lonely Island and Michael Bolton's "Jack Sparrow

My three year old son Declan is compulsive in his consumption of entertainment. If he wants to listen to a song or watch a video, he wants to do it a hundred times, preferably in a row. I can relate. I don’t know how many times I’ve listened to The Lonely Island’s “Jack Sparrow.” If I had to throw out a completely bullshit but extremely large number for it, it’d be, I dunno, in the low three thousands. 

For whole weeks, I would listen to pretty much nothing but “Jack Sparrow.” It got to the point where I started to wonder if I had some weird neurological condition that blocked me from wanting to move on beyond that one insanely infectious, catchy song. But no, I think listening to “Jack Sparrow” without end for a good chunk of my existence is less pathological than a matter of good taste.

Besides, there’s just so damn much to “Jack Sparrow”, and all of it speaks very directly to my sense of humor. For starters, the song essentially begins with a behind-the-scenes skit, and I love me a good skit, as well as a bad one. I may actually prefer terrible skits, so it's a good thing there are a lot of them, particularly in hip hop. In this case, the behind-the-scenes skit begins with The Lonely Island in the studio when their latest collaborator is buzzed in: Michael Bolton.


The trio and Michael Bolton awkwardly exchange pleasantries, the way white men do, and Bolton stiffly explains the reason for his tardiness: “I’m really sorry I’m late. I got caught up watching the Pirates of the Caribbean marathon. Have you seen those things?” The Lonely Island mumblingly assures Bolton that they have seen the Pirates of the Caribbean movies in what only appears to be a complete non-sequitur.

The song’s premise has Lonely Island agreeing to record their sleazy new dance track with Bolton without hearing the “big, sexy hook” he wrote for it. Now, I’m not a professional musician, merely someone who has listened to the work of literally hundreds of professional musicians, many award-winning, over the course of my many years on the planet, but I don’t think the recording process works that way. I imagine there has to be a lot of clear communication between collaborators or mishaps will happen. Comical mishaps. 

“Jack Sparrow” tips its hand ever so slightly with its title, and with the opening spoken-word interlude involving Bolton gushing about Jerry Bruckheimer and Gore Verbinski’s bloated handiwork, but it otherwise begins like a straightforward club song, with the fellas of Lonely Island posturing about hitting the club strapped for a night of drinking, flirting and debauchery. 


There’s a certain absurdity to the song even before pirates re-enter the equation. After all, The Lonely Island, are nice Jewish boys, not sneering bad boys sneaking shanks and handguns into clubs during lost nights spent in feverish pursuit of meaningless sex with models and debutantes. Yet the non-Michael Bolton half of the song finds them posturing like hip-hop/R&B playboys all the same. 

Then The Lonely Island’s sordid club track shifts musically from electro-funk iciness to mock-epic bigness and Bolton defiantly booms, “This is the tale of Captain Jack Sparrow, pirate so brave on the seventh seas! A mystical quest to the Isle of Tortuga, raven locks sway on the ocean's breeze!” 

 He's into it! 

He's into it! 

That’s a hook only belongs in a song about Captain Jack Sparrow, pirate so brave on the seventh sea, and even in a sea shanty about Captain Jack Sparrow, the lines about a “mystical quest to the isle of Tortuga” and “Raven locks sway on the ocean’s breeze” would register as decidedly histrionic and over-the-top. 

Much of the genius of “Jack Sparrow” lies in its choice of title and subject. I’ve seen and enjoyed the first Pirates of the Caribbean movie (within reason), and obviously there must be people who adore these films, and these characters, some of them even older than five. These movies gross billions, yet something about them seems weirdly obsession-proof. So the idea of a grown man of a certain age like Bolton obsessing about these children’s movies to this extent is exquisitely preposterous. 

The Lonely Island’s Akiva Schaffer tries to course-correct from within the song itself when he acknowledges the track’s wrong turn with a tense, “That was kind of weird” before re-establishing the song’s setting from the high seas of the 18th century to an upscale club in the present. 

Bolton keeps undermining his collaborators by continually dragging focus back to the Pirates of the Caribbean cinematic universe. Slotted uncomfortably in the hype-man role, Bolton keeps blurting out phrases related to his beloved Pirates of the Caribbean but most assuredly not related to what anyone else is rapping about, including female lead Keira Knightley, Johnny, Depp, Davy Jones, and my personal favorite, “Giant Squid.”

Bolton sings admiringly of The Pirates of the Caribbean's “pauper of the surf” and “jester of Tortuga” until Akiva snaps and sternly tells him, “Michael Bolton, we’re really going to need you to tighten up” to which he retorts, “Roger that, let me try it with another film.” 


The poor dope does not seem to realize that the problem lies not in his cinematic choice, so he shifts gears and offers, “Life is a box of chocolates, and my name is Forrest Gump.”

Again, I am no music world professional, but I’m guessing a lyric like “My name is Forrest Gump” is only appropriate in a song about Forrest Gump, not a song about hitting the club with your boys in search of some action.

In his bid to find the perfect cinematic character to sing about for the chorus of song that should have nothing to do with movies, Bolton flits from Forrest Gump to Erin Brockovich and then finally and conclusively to Tony Montana when he rhymes, “Erin Brockovich is my name” with “Then you can call me Scarface snorting mountains of cocaine.” 

Incidentally, I would be justified in my feverish, obsessive love of this song for that rhyme alone, or for “Jack Sparrow” finally uniting Forrest Gump, Tony Montana and Erin Brockovich as lesser characters in what’s either a hedonistic club song or a tribute to a popular Disney icon beloved by children. 

Lonely Island is so defeated by their collaborator’s bizarre fetish for implementing movie catchphrases places where they do not belong that they ultimately give up and decide that while Tony Montana, a fictional character who died in 1983, doesn’t really have anything to do with their song or what they’re singing about, he’s “close enough” and decide to let Bolton run with his idea of making this pop/rap/dance hybrid a tribute to Brian DePalma’s gangster classic.  

 Bolton shown enjoying some down time on the music video's set.

Bolton shown enjoying some down time on the music video's set.

“This whole town’s a pussy just waiting to get fucked!” Michael Bolton sings climactically in character as Tony Montana as the song goes gloriously off-track and ends up someplace several universes away from where it began, cinematic or otherwise. The Lonely Island's relationship with Saturday Night Live and Lorne Michaels has helped them get away with an awful lot, but it's nevertheless pretty goddamn impressive they somehow managed to convince Michael fucking Bolton to sing "This whole town's a pussy just waiting to get fucked" at such a volume and with such apparent enthusiasm.


“Jack Sparrow” changed Michael Bolton’s career and the public perception of him. He isn’t funny here despite being stiff and unnatural: he’s hilarious precisely because he seems so off. That’s similarly true of the Michael Bolton Netflix Valentine’s Day special Lonely Island worked on with Scott Aukerman, which isn’t as funny as “Jack Sparrow” (what is?”) but is nevertheless a worthy follow-up. And this song paved the way for Bolton to appear in the climax of Lonely Island’s wonderful, if under-seen vehicle Popstar: Never Stop Never Stopping. 

"Jack Sparrow" was so funny and so memorable that we as a culture stopped laughing at Bolton and started laughing with him. He didn’t exactly stop being the butt of jokes, or a joke himself, but with his wonderfully wooden comic turn here, Bolton proved forever that he's most assuredly in on the joke, and that when Lonely Island was involved, the joke could be weird and wild and unexpected and wonderful and above all else, very funny. 

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