Jack Sparrow (feat. Michael Bolton)

The Lonely Island invite Michael Bolton to the studio to collaborate on a hip-hop club track. Bolton claims he wrote them "a big, sexy hook" — but when the mic is his, he launches into a full-throated power ballad about Captain Jack Sparrow from Pirates of the Caribbean. Each time the trio tries to steer the song back to the club scene, Bolton hijacks the chorus again, pivoting through increasingly unhinged movie tributes: Forrest Gump, Erin Brockovich, and finally Scarface. The music video features Bolton in full Jack Sparrow costume, including red bandanna, heavy eyeliner and goatee, filmed over two days including crane shots at Brighton Beach, Brooklyn. By the end, The Lonely Island give up entirely, with Andy Samberg noting that Bolton is a "major cinephile." Bolton closes by quoting Jerry Maguire: "You complete me!"

The song debuted on SNL on May 7, 2011, marking Michael Bolton's first SNL appearance since 1991. Bolton recorded his vocals on a night off in Atlanta, with The Lonely Island directing via Skype. Bolton was initially reluctant due to the coarse language; lyrics were revised multiple times at his request. The video amassed over 249 million YouTube views as of 2026, making it one of The Lonely Island's most successful videos. The song appeared on The Lonely Island's second studio album "Turtleneck & Chain" (2011). A re-recorded version appears on Michael Bolton's album "Songs of Cinema." Bolton performed an unplugged version during his 2018 Netflix special "Michael Bolton's Big, Sexy Valentine's Day Special." Chart peak: #2 in Norway, #6 in Sweden, #69 on the US Billboard Hot 100.