A mystical quest to the Isle of Tortuga...

How Michael Bolton saved Lonely Island from itself

The singer's "SNL" collaboration marks a new high point for the comedy trio, and it's not so bad for him, either


Drew Grant
May 10, 2011 8:01PM (UTC)

Lonely Island's second album, "Turtleneck and Chain," drops today, and I'm actually thinking about buying it. I've always been a fan of the "Saturday Night Live" trio, because who among us was able to watch "Jizz in My Pants" or "I'm on a Boat" without cracking up? But parody groups -- whether done by Weird Al or sexy hipster Andy Samberg -- are by definition a novelty act, and when Lonely Island's "Incredibad" came out in 2009, I was content to just watch the videos the group had released.

This might change with "Turtleneck and Chain," especially after this weekend's mind-blowing performance with Michael Bolton for the "SNL" digital short "Jack Sparrow." I've been singing this song nonstop for the past 48 hours straight. It's some of the group's best work, and I'm pretty sure it's the best thing to happen to Michael Bolton's name since "Office Space." If you haven't seen the video, you need to fix that immediately:

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Note: This song is best watched on a continual loop after first viewing so that you're able to get all the background interstitial dialogue. (Jorma, Andy and Aviva's reactions are the best, even when they're just shaking they're head and going "What?" Although, again, Bolton wins with his pirate's hat when he pops up singing, "Now back to the good part!")

Despite pulling huge names like Beck, Snoop Dogg and Rihanna ("Shy Ronnie" runs a close second for best video these guys have come up with since their last album) for "Turtleneck," there is a reason that "Jack Sparrow" premiered the weekend before the CD release. Bolton is far and away the best guest track in the lot, and he succeeds specifically because he's not what Lonely Island fans think of as cool. Sure, Justin Timberlake singing "Dick in a Box" is funny, and Akon lending a verse to "I Just Had Sex" gives the song a much-needed shot in the arm, but "Jack Sparrow" works because it's so far outside these guys' comfort range. This really is a Michael Bolton song, carried entirely on the strength of his voice and not, like most of the other numbers on the album, by auto-tune. If the mashup of hip-hop and a Michael Bolton hook wasn't funny enough by itself, the song's numerous blockbuster references make it an instant classic.

And I'm not alone in feeling that way: The video has been viewed over 2.5 million times on YouTube since Saturday. Michael Bolton himself isn't ruling out a tour with Samberg and company, telling Entertainment Weekly that he would gladly reprise the role of himself. One character Bolton doesn't want to do again, though? Erin Brockovich in drag:

"I was terrified to look in the mirror. I tried to avoid it. I noticed when they were finishing me up as Erin that the crew started reacting in this really uncomfortable way. As I walked past, people were clearly uncomfortable. At one point I was breast-feeding the baby ... With Erin, I just kind of wanted to get those clothes off and take a shower."


Drew Grant

Drew Grant is a staff writer for Salon. Follow her on Twitter at @videodrew.

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