The Lonely Island - Jack Sparrow (ft. Michael Bolton)

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"Jack Sparrow" is a song by American comedy troupe The Lonely Island featuring singer-songwriter Michael Bolton. The song and music video debuted on Saturday Night Live as an SNL Digital Short on May 7, 2011. The plot follows the troupe inviting Bolton to work on a new hip hop track, in which the members rap about meeting at a club and taking women home. Bolton ruins the group's song by instead singing choruses about the Pirates of the Caribbean film series and their primary protagonist Captain Jack Sparrow, but also with references to Forrest Gump, Erin Brockovich, Scarface and Jerry Maguire.

The track was written by The Lonely Island during the production process of their second album, Turtleneck & Chain, in the summer of 2010. With an initial premise concluded, the members settled on contacting Bolton to make an appearance for the track. The trio relentlessly begged Bolton, who was initially uneasy to commit due to the track's coarse language. After recording the track, the troupe recorded a music video with Bolton as Jack Sparrow, protagonist of the aforementioned film series. The clip, on which Bolton noted the trio intended to go "above and beyond", was recorded with tremendous energy and focus over two days. After its initial debut as an SNL Digital Short, the video was uploaded to YouTube and subsequently attained much online popularity. In addition to its status as a viral hit, the song has received positive reviews from many media commentators and reviewers.

The song's music video was shot over two days, with what Bolton called a "tremendous amount of energy and focus". The video's filming took place for 16 to 18 hours each day, and crane shots of Bolton on the beach were filmed at Brighton Beach, Brooklyn. On his website, Bolton commented that working on the song "was one of the highlights of my career and most memorable experiences of my life". He added that he felt uncomfortable about dressing up in drag as Julia Roberts in Erin Brockovich, and that he was "terrified to look in the mirror".

Bolton appears in costume as Jack Sparrow for a great deal of the video, complete with Sparrow's signature red bandanna, heavy eyeliner and goatee. The music video featured models Jenny Albright and Kate Bock in the club scene, and Danish singer Amalie Bruun as Jenny Curran, Forrest Gump's wife.

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Artist: The Lonely Island
Video title: Jack Sparrow (ft. Michael Bolton)

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Category: Hip-Hop
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