Jack Sparrow by The Lonely Island: Top Ten Animated Gifs of Michael Bolton

Posted by Eric Smith

When Melissa brought this video to my attention the other day… there might have been tears from all the laughter. Despite Andy Samberg and his crew’s extreme disapproval in the video, there is no denying that Bolton’s hook was, indeed, as “big and sexy” as he promised. I found myself whistling it on the way to work, out at lunch, while writing pitch emails, etc. I just can’t get away from it. Hell, I can’t get enough of it. So, like any good blogger, I went to the Internet to get even more.


Warning: Kinda NSFW, Put On Headphones


And behold, Tumblr had exploded with animated Michael Bolton .gifs, showing the legendary musician at his comedic best.

To celebrate the video the entire Quirk office has come to love, I’ve posted my top ten animated .gifs from all wakes of the Tumblrsphere. If you think you can make one that’s better, email me ([email protected]) your .gifs! I’ll repost my three favorites and send the creators a copy of the Captain Jack Sparrow Handbook… which I seriously need to get into Bolton’s hands. There has to be a way.

“Rollin’ up…” via KatieB1013


“This is the tale, of Captain Jack Sparroooow…” via Electric Dream Machine


“He’s the Pauper of the Surf…” via Ice Cream Kitty

“Now back to the good part!” via Ice Cream Kitty

“Life is a box of chocolates, and my name of Forrest Gump…” via Murphy Tinker

“Okay then I’m a legal aide…” via Glen Coco

“On mountains of cocaaaaaine…” via p0rcelainblack

“Reloooooading…” via Doctor Dude

“This is the tale, of Tony Montana…” via Confessions of a Movie Nerd

“You complete me…” via Sanity’s Oblivion

Eric Smith


ERIC SMITH is the cofounder of Geekadelphia, a popular blog covering all-that-is-geek in the City of Brotherly Love, as well as the Philadelphia Geek Awards, an annual awards show held at the Academy of Natural Sciences. He’s written for the Philadelphia Inquirer, Philadelphia Weekly, and Philly.com