Getting to that finish line, though, took a lot of patience. There wasn’t a time when anyone was whining or complaining about how late the days were running.” “There wasn’t a time when anyone was looking at their watches or the clocks. “It was so much fun from start to finish,” Bolton recalls. Oh, and if you ask him to focus up? He’ll insist on listing all his favorite films like a proto-Letterboxd user. And the pauper of the surf and the jester of Tortuga. The setup is simple: Andy Samberg, Jorma Taccone, and Akiva Schaffer enlist him to contribute vocals and a “big, sexy hook” for their song about hitting the clubs, but Bolton would much rather sing about the cinematic joys of Davy Jones and giant squids. Sandwiched between Helen Mirren’s Magical Bosom and a 3-Way with Justin Timberlake, Bolton - the face and follicles of the adult-contemporary genre as we know it - jumped ship from his straightlaced persona to croon about his flourishing obsession with the Pirates of the Caribbean franchise. Let’s rewind back to May 2011, when SNL Digital Shorts were being traded around the internet like casefuls of pilfered doubloons. Yes, of course, it’s Michael Bolton and “Jack Sparrow.” This is the tale of a brave balladeer who took a mystical quest to the Lonely Island and sailed away with what might be the biggest hit of his career. I realized I needed to start having fun.” What do I wish I had invented?ĮSQ: You want to take credit for inventing anything? We'll give it to you.“I spent a lot of years taking myself and my career a little too seriously. MB: Even if I did, I don't know that I'd ever. Are there any innovations you'd like to take credit for now? Last question: Kenny G recently sort of took credit for creating the Frappuccino. I hope he considers it flattering.ĮSQ: Of course he does. And I'm such a huge fan of Scarface that's why Andy put it in there, actually. I haven't spoken to him about it, but I understand he's happy about my Scarface. It aired Saturday-I was there-and on Sunday it went insane: a million views a day.ĮSQ: Did Johnny Depp or Al Pacino compliment your performance? And then I flew up to New York and we filmed it in two days. They were on the phone producing-they're hands on. Seven months later, I got an email from Andy and it was the new idea-the new concept-and I said, "Oh my God, I could do this." And they said, "Where are you?" And I said, "Atlanta." They sent me to a studio, and I sang it. MB: They said, "So let's work on it." I figured they were too busy, they were just saying that they would tweak it. So I said to them, "I really want to work with you, but I don't want to frighten the hell out of my core audience and have them go 'why is he doing this?'" I wanted to work with them, but the language in the first original concept was pretty, um, nasty. MB: The Justin Timberlake "Dick in a Box" one was hilarious. MB: No, I met with them and I immediately wanted to do something with them, because I loved their other skits that I've seen, their other shorts. We filmed it here in New York-Brighton Beach, which is where the ship was.ĮSQ: Did you immediately agree to it, or did The Lonely Island guys talk you into it? We actually worked about two 16-hour days. MICHAEL BOLTON: I remember laughing my ass off for 24 hours. Read on for his story of making the song, thoughts on Kenny G, and what he wishes he'd invented.ĮSQUIRE.COM: You were part of one of the best digital shorts ever. Esquire recently caught up with Bolton on the red carpet at SNL's 40th anniversary special. Again, he played himself, though he was too distracted by visions of Johnny Depp's dreads to actually lay down a new track, and paid homage to Forrest Gump, Erin Brokovich, and Scarface. Back in 2011, he starred with The Lonely Island in the Saturday Night Live digital short Jack Sparrow. Now that we've seen Michael Bolton play himself in Office Space, let's revisit the first time he flaunted those comedic chops.
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