Jack Sparrow

Album: Turtleneck & Chain (2011)
Charted: 69
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  • In this song, the guys from The Lonely Island team up with Michael Bolton to create a club banger that will blow some minds. Bolton shows up and tells them he's written a "big, sexy hook," and also that he's been watching the Pirates Of The Caribbean movies.

    The song starts off all gangsta, with the boys blinged-out, rolling into the club where they drop their American Express Black Card at the bar and start making their moves. But when they get to Bolton's hook, it's all about Captain Jack Sparrow from Pirates Of The Caribbean - big, but not sexy. The action returns to the club, but Bolton keeps pulling it back to his pirate theme, eventually stretching it to other films: Forrest Gump, Erin Brockovich, and Scarface. Turns out Michael Bolton is a big-time cinephile.
  • The Lonely Island is the comedy team of Andy Samberg, Jorma Taccone and Akiva Schaffer. They specialize in original songs with hilarious videos that often aired on Saturday Night Live, where Sandberg was a cast member and Taccone and Schaffer were writers. By 2011, they were so popular that their songs were released as singles and got huge view counts on YouTube after they aired on SNL.

    Michael Bolton was a big fan. When Samberg called him with a pitch, he was all in. At their first meeting, Bolton told them his daughters were very excited that he was working with them; Samberg said his mom was stoked that he was working with Bolton.
  • According to Bolton, "Jack Sparrow" was a lot dirtier when it started. The Lonely Island had to clean up the language to make it work for Bolton, who didn't want anything so filthy it would disturb his fanbase.
  • Bolton really is a big Scarface fan, which is why The Lonely Island wrote that into the ending.
  • Bolton was one of the biggest pop stars of the '90s, landing hit after hit with grandiose ballads for the ladies (you never would have guessed that he once fronted a hard rock band). "Jack Sparrow" showed his sense of humor and endeared him to the younger crowd, increasing his cool factor considerably. After the video took off, Bolton did more comedy, guesting on the sitcom Two And A Half Men and appearing Popstar: Never Stop Never Stopping, another Lonely Island production.
  • Other Lonely Island videos include "I Just Had Sex" (featuring Akon) and "Motherlover" (featuring Justin Timberlake). "Jack Sparrow" is one of their most popular, with well over 200 million views on YouTube.
  • The beat was created by the British producer Michael Woods. Under the name Warrior, he makes dance music popular in UK clubs.


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