"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 his favorite movies, like 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 and music video open with Michael Bolton entering the studio to meet Samberg, Schaffer, and Taccone. He apologizes for being late, as he was "caught up watching the Pirates of the Caribbean marathon". They discuss a song they are working on and Bolton says he wrote "a big, sexy hook" for it. They begin recording, with Samberg and Taccone rapping during the first verse about going to a club and partying with women. When it comes to Bolton's chorus, he begins to sing about Jack Sparrow, much to Lonely Island's chagrin. The subject matter switches back to the club in the second verse, but Bolton interrupts again, singing more about his hero and his "yearn[ing] for adventure."

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