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, Scarface and Jerry Maguire.

After its initial debut as an SNL Digital Short, the video was uploaded to YouTube and subsequently attained much online popularity, amassing more than 235 million views as of October 2023.

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."

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.

"[10] 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!"

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.

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.

[9] 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.

"[14] (The last sentence is an obvious reference to the phrase sung in the video where Bolton pops into frame wearing a pirate hat, again hijacking the Lonely Island club theme.)

[15] The song was released as a digital single through the iTunes Store shortly afterwards, and the music video uploaded to both The Lonely Island's official website and YouTube.

Mikael Wood of the Los Angeles Times called "Jack Sparrow" the sharpest comedy from Turtleneck & Chain, writing that Bolton's "patented power-soul singing blurs the distinction between the silly and the sublime.