"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 its primary protagonist Captain Jack Sparrow, but also with references to Forrest Gump, Erin Brockovich and Scarface.

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 over two days. After its initial debut as an SNL Digital Short, the video was uploaded to YouTube and subsequently attained much online popularity, amassing more than 247 million views as of September 2025. In addition to its status as a viral hit, the song has received positive reviews from many media commentators and independent 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."

The musicians' complaints about Bolton's singing are heard in the background, and they tell him they need him to focus on their song. Misunderstanding, he suggests his hook might work better with another film and then sings about being the title character of Forrest Gump, Erin Brockovich, and finally Scarface, with them continuing to complain about his off-subjects. The trio eventually give up by the end of the song and cut off Bolton, with Samberg noting that Bolton is a "major cinephile", and Bolton quoting Jerry Maguire: "You complete me!" Bolton also appears as backing vocals during the club-oriented verses, singing off-topic and unrelated Pirates-themed lines, such as "Keira Knightley", "Johnny Depp!" or "Davy Jones! Giant Squid!" The track parodies Bolton's association with love ballads, with the entire ballad dedicated to Sparrow.

You want to work with guys like this. But at the same time I get invitations to perform at the Vatican! It could be potentially uncomfortable. And in the first few approaches some of the language was just so intense and off-color.

"Jack Sparrow" was written by The Lonely Island during the summer of 2010. The comedy troupe, in the same fashion to the recording process for their debut, Incredibad, rented a house in Los Angeles and created a makeshift studio where they would record songs. The troupe had the premise for the song initially, and while trying to find the perfect person for the guest spot, Schaffer mentioned Michael Bolton, and according to Samberg, "our eyes all widened. We decided, in that moment, that we wouldn't rest until we got him to do it." The trio reached out to Bolton's management, and Bolton admitted that he was a fan of the troupe's musical comedy. However, he was concerned regarding the harsh language used in the first few takes of the song. "They were sending me lyrics and I was reading them and I was thinking, 'This is funny.' Then I’d get to another line, [...] and I would say, 'Nope, I don't think I could be intoxicated enough to read this line,'" recalled Bolton. The track's lyrics kept transforming with each version per Bolton's request to tone down the "intense" and "off-color" language but the trio stayed with the singer throughout due to their desire to have him appear in the song. Bolton appreciated their making his requested alterations to the song. The troupe was eventually able to get Bolton to do the song after they "begged him over and over again until he finally cracked," according to Andy Samberg. Bolton's portions of the song still include one use of the words "fuck" and "pussy", both quotes from Scarface.

Bolton recorded his vocals for the track on a night off in Atlanta, with instructions from The Lonely Island through Skype.

Following the shoot, Bolton posted a message to his website: "Working with Andy, Akiva and Jorma on the Jack Sparrow digital short was one of the highlights of my career and most memorable experiences of my life. For the few people on the planet who might not know, these guys are brilliant, funny and beyond super talented. They made me do things I never would have expected to be comfortable with and I'm so glad I did. Truly grateful to be a part of this project and CANNOT WAIT for the chance to work with the guys again. Now Back To The Good Part." (The last sentence is a reference to the phrase sung in the video where Bolton pops into frame wearing a pirate hat, again hijacking the Lonely Island club theme.)