The Top Five Weirdest Playboy Appearances By Musicians

Categories: Lists
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Coming soon to a Playboy near you?

After all those Twitter cries for help and suicide attempts last month, Sinead O'Connor has apparently found a new reason to stay alive: she wants to pose for Playboy before she dies.
"There's so much I [would have] liked to do when I was younger and I was too miserable and Irish," she told the U.K.'s Word Magazine. "A Playboy shoot is on my bucket list." The singer also expressed an interest in doing "some interview in weird sex gear," before gleefully declaring: "You can talk about serious issues while you're bollock naked, on all fours, in your dog collar!"

In Sinead's honor then, we'd like to present the Top Five weirdest Playboy appearances by musicians. You're welcome!

5. Debbie Gibson
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It's not that the shoot for this one was particularly odd (except for the photos in which they put so much make-up on her that she looked like a new transvestite), but the fact that Debbie Gibson was doing Playboy was -- and is -- definitely frickin' weird. She was so squeaky clean in the '80s, it had never occurred to us that she even had lady parts! Let alone lady parts that she would one day be hiding under weird diamante belts for Hugh Hefner. Shake your love, indeed.

4. Tiffany
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There was something overwhelmingly sad about Tiffany's shoot for Playboy that, to this day, we can't quite put our fingers on. She grinned throughout most of the shoot, so technically this should've been fun and bubbly on some level. But it was just... depressing. Her mouth may be smiling and her body may be cooperating, but something in Tiff's eyes told us all she really didn't want to be there.

3. Nancy Sinatra
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As we all know, Frank's daughter spent the '60s and '70s being a sexy badass and singing about walking all over people in her incredibly foxy collection of boots. Then she went and weirded everyone out by waiting til she was 55 years old to go and do Playboy. It's not that she wasn't still beautiful, and not that her body wasn't in great shape. The problem was that she looked extraordinarily uncomfortable throughout the entire thing, which made the pictures equally as uncomfortable to look at.

2. Mariah Carey
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The weird thing about Mariah's shoot for Playboy is that she never actually took her clothes off. She didn't get naked. Hell, she didn't even go topless. Instead, she lounged around in her lingerie showing more or less the exact same amount of skin she was showing in her videos at the time. Completely and utterly pointless.

1. La Toya Jackson
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In a family of weirdos, Latoya still remains one of the strangest, and her Playboy shoot embodied that completely. Latoya posed covered in piles of snakes, did strange things to/on a motorcycle and -- this was our favorite one -- posed naked on a rocking horse with her butt in the air. It's worth Googling that last one... hilarious.

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12 comments
el_brio
el_brio

Thanks for not showing titties.  That would have offended an disgusted the people who followed the links to this article.

bfg666
bfg666

I agree with Jeff here. A topic about Playboy usually more or less guarantees a certain level of nudity, and people who click on links to nudity usually enjoy it. OR they are uptight morons who click on those links just to do some trolling, often christian moralists who are offended by pretty much everything in the world and don't realize that by behaving that way, they contradict the teachings of their idol Jesus Christ.

Jeff Paterson
Jeff Paterson

I don't know if you're trolling or literally weren't expecting titties when you clicked.  I was!

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Ratso
Ratso

Weirdos is an understatement. Sheesh.

Kinglife2027
Kinglife2027

You assholes are UTTERLY rude. "A family of weirdos." Really really rude. Assholes!

Asdf
Asdf

Weirdos. All of them.

bfg666
bfg666

 What? As if it wasn't true!

Artgum44
Artgum44

 Hey Janet, chill out! ;-)

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