The Top 100 Songs of 2011 -- #78: "Jack Sparrow" - The Lonely Island

The Lonely Island will always get points for a few things, among them being an eclectic creativity and a simply random sense of humor. Whether you're watching their digital shorts on Saturday Night Live or simply listening to one of their songs, the productions of Andy, Jorma and Akiva always tend to leave folks wondering 1) How they came up with their material, and 2) How they pulled it off to such great effect.

The group released Turtleneck and Chain in 2011, the follow-up to their uproariously popular debut. Following the modest hit "I Just Had Sex" with R&B singer Akon (made better by its hilarious video), Samberg and Co. released "The Creep" with Nicki Minaj, another runaway hit.

So, how to top the first two singles' success? Two words, two very unexpected words: Michael Bolton.

No one saw it coming. No one expected a collaboration so mismatched and with a singer so out of the public eye that not even a new album that charted modestly on the Adult Alternative charts could bring him back to relevance. Bolton's prominence in the last decade had existed solely due to the mention of his name during Mike Judge's Office Space film. Musically, he was dead to the world, a laughing stock at that -- want cheesy '80s and '90s impassioned adult pop rock that will deprive any male who listens, unforced, to it of his man card.

Granted, that still holds true for Bolton's music. But at least we can finally point at something from Bolton's career from the past 15 years and say, "Hey, but he did this. And it was awesome."

In "Jack Sparrow," Bolton promises a hook that will take The Lonely Island's club-banger verses to the next level. But it doesn't exactly work out that way. Bolton takes the song to the next level alright, albeit in a completely different direction. "This is the tale of Captain Jack Sparrow," sings Bolton on the chorus, suddenly making the song about Disney's Pirates franchise. The Lonely boys are reasonably confused.



"Okay, turns out Michael Bolton is a major cinephile," they muse after Bolton namedrops Forrest Gump, Scarface and more (speaking of, the song is worth it if only to hear his Tony Montana impression).

"Jack Sparrow" ends up the best song off Turtleneck and Chain for sheer hilarity. It was uproariously funny during its initial run as a digital short, and while some of the visual comedy is lost in translation, the song is still hilarious. It will be hard for the boys to top this.