The Funniest Michael Bolton Cameos, Appearances, in the Last Decade

Michael Bolton has taken a lot of flack over the years in comedies, interviews, and various other mediums. Give him some credit, he’s been a good sport and has rolled with for the last decade or so and actually made spoofs of films in which he was mentioned in a less than congratulatory manner. It takes a person with a good sense of humor to actually laugh at themselves and then go the extra mile to laugh some more. Hats off to you Mr. Bolton, even a person that’s not a fan of your music would get a good laugh out of these clips.

Here are a few clips you might get a kick out of.

5. Office Space

Michael made such a big deal out of being given the same name as Michael Bolton that it became a big part of the appeal that Office Space brought to fans. In doing so however it really kind of slammed Bolton repeatedly over his talent and the fact that so many people find it necessary to make a joke out of his career. But hey, Bolton got back at them just a little by making his own spoof, and it was pretty funny really.

4. Singing Barista

Would it even be possible to see Michael Bolton as a barista? More than that, would it even be feasible to say that he could possibly go undercover anywhere and not be known? I think most people would laugh their butts off if they got serenaded by Michael Bolton when picking up their drink. You know who he reminds me of though? The guy in My Name Is Earl that had to sing absolutely everything. His voice is way better though.

3. Fresh Off the Boat

You might like this show or you might not even know about it but this clip is kind of funny for the simple reason that it makes Bolton’s character look kind of like a conceited jerk who needs to prove himself in some way. The desire to destroy Kenny Rogers, either the restaurant chain or the man I don’t know, is also kind of amusing in a creepy, sort of mania-driven manner.

2. Two and a Half Men

A lot of guys might quote Michael Bolton lyrics when making a proposal or taking their girlfriend out to dinner, but who actually goes and gets the man himself to serenade them? It’s an awesome gesture really but feels a little overplayed given the woman’s reaction. Just to make the night worse, when your roommate’s mother meets the man she openly tells him that she has a special device named after him. Yikes, oy, and oh the humanity.

1. Jack Sparrow

The guy has an awesome sense of humor. Not only does he ingratiate himself to others but he knows how to go completely off the rails and still make it sound good. It still sounds nuts since the guys can’t even follow his line of thinking while he’s singing, but it’s done in such a way that you really don’t care because it’s so hilarious.

Michael Bolton is many things, but he’s definitely a good sport when it comes to making fun of himself. And more than that, the fans seem to enjoy it.

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