2011 / Video / SNL Digital Short and comedy music video
Jack Sparrow (feat. Michael Bolton)
The Lonely Island asked Michael Bolton for a club-rap hook. He delivered an uncontrollable Pirates of the Caribbean sequel.
The original is off-site. HAHrchives preserves the story and a route back to it.
What happened
The trio tries to record a club track, but Bolton keeps returning in costume to sing sincere plot summaries of increasingly unrelated movies.
Where it came from
The Lonely Island released Jack Sparrow as an SNL Digital Short on May 7, 2011, with Michael Bolton turning a rap-session cameo into a movie-musical derailment.
Why it mattered
It is 2011 comedy working across television, YouTube, and pop music at once, powered by Bolton’s total commitment to every unnecessary tribute.
How it spread
The sketch moved from Saturday Night Live into a shareable music video as Turtleneck & Chain arrived.
Keep going
The same corner of the internet
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Three men in bad suits turned social awkwardness into a dance move.
Historical figures, fictional characters, a beat, and the question every comment section wanted to answer: who won?
A Queen anthem, a Muppet chorus, and one very unproductive video conference.