Tiffany Vs. Debbie Gibson, Playboy Showdown
Flipping, flopping and serving hoes like flapjacks for over 30 years, it’s the WWJ Hot Bitch of the Day. I was thinking out loud at work today about which lovely lady would be lucky enough to grace the pages of the HBOTD, when my boss Danny suggested I do something for the older visitors to my site. He wanted to see Tiffany, that teen pop star from the 80’s, Playboy spread from a few years back. It sounded like a good idea, but I decided to make it better by also including the Playboy pictures of Tiffany’s mortal enemy, Debbie Gibson. If you are in your mid 20’s to your mid 30’s and claim that you didn’t own one of their CD’s you’re a fucking liar and just a horrible person. I honestly can’t remember how any of Debbie Gibson’s songs went, but since Danny mentioned Tiffany to me today, I can’t get “I Think We’re Alone Now” out of my head. I am sure you will also find yourself humming it as you scan over these pictures. Thanks to Danny for the suggestion and huge thanks to WWJ’s own Internet Gangsta, Tim, for helping me locate the Tiffany pics. Now I give you the world debut of WWJ’s Playboy Showdown!! Vote for your favorite naked 80’s teen pop star in the comment section.
As always send hate mail to jimmy@ElectricYouth.com
Peace love and hair grease
TIFFANY
Debbie Gibson
THE END
Labels: Debbie Gibson, Tiffany
posted by WWJ at 1:15 AM
35 Comments:
I would of died to see these in the 80's.
You are a god!!! thanks for these!!
Tiffany is far more rackalicious. Carpet matches the drapes, too (and she's not afraid to show it). Definitely Tiffany
Although I think Debbie Gibson has a prettier face, Tiffany has the kick ass body and almost perfect boobs. Too much hair on top but I'd munch her carpet for days!! Probably wouldn't kick either one out of bed, if ya know what I mean. Great pics...thanks!
I say Tiffany for sure. Is it even close?
Debbie has a much prettier face than Tiffany, but Tiff is stacked hard.
Id say Debbie is the winner because of her face. She can always buy some boobs haha.
Thanks for the pics ;)
Tiffany is definately the winner. Much better body and suprisingly pretier than Debbie.
You're all mad. I loved Tiff back in the day, but she hasn't ages as well as Debs, who still has the body of a 20yr old.
Twenty years later and Im switching from Tif to Debs
Tiffany's has gotten better looking with age. Debbie is very pretty, but Tiffany has it all. Nothing better than a hot redhead.
Debbie Gibson looks kinda tweaked and should have not gone that route. . . Tiffany, how-ever, makes me Thick. . . WoW.
Tiffany hotter. Nice tits!!
I was seriously in love with Debbie Gibson in the 80's, but hands down the winner is Tiffany, with her gorgeous face and body.
Debbie has no tits to speak of, and her face hasn't improved with age, as far as I'm concerned.
Now where was that hand cream...
Dr. Jeff say's: I can't choose! I'd do em both!
Poor Deborah looks uncomfortable, while Tiffany comes off as fuck me hot... No question Tiffany dominates this matchup between the 2 girls I wanted to fuck when I was in school.
WHAT THE FUCK??? YOU'RE ALL CRAZY!! I'm a bi chick and there is NO contest that Debbie is HOTTER! WAY hotter! Tiffany's boobs almost look fake. Debbie's might be small, but they still rock. And this is coming from a boob lover with a size 38J rack! And what's with her lips?? Can anyone say Collagen?? lol Debbie's face is perfect. Absolutely perfect! Not to mention her photos are much more creative. She looks good in everything she does. And, Tiffany needs to shave. ew. If you voted for Tiffany, you're fucking DEAD WRONG! If I could do either one of em, I would pass Tiffany by and jump on Deb! If Tiffany asked to join, I'd turn 'er down. For sure. However, if Eva Mendes wanted to join... ha
Tiffany is a lot better looking than Debbie. I wouldn't tern either away but if I could only choose one it would be Tiffany. I't might be that red hair(I love red heads).
Seriously, if you're not voting Tiffany you've got cabin fever. I've never been a big fan of blonds either way, but Tiffany is built like a brick house. It doesn't get any more solid than that. Legs, breasts, face, the whole nine yards. She doesn't need the airbrushing that Playboy provides for Debbie Gibson.
I wanna milk Tifanny's fat titties real good but I'd have to put a pillow her face while doing it cuz it be busted now.
meh on all counts. too little, too late
Debbie *all* the way.
Tiffany is displaying that classic, screamingly awful "looks American at 100 paces" style of makeup where everything looks fake before she's even started, from bleached teeth to botoxed lips to silicon boobs to greasy-looking hair extensions. Debbie may be every bit as airbrushed, but at least she's gone for the far-more-attractive understated look. Tiffany just looks like a freak show.
In the 80's I couldn't decide - but Tiffany comes across like she's been doing porn professionally (and I've seen my fair share of porn!)
You'd pick Tiff as your whore, coz she's got more to hold on to and generally fuck and suck.
Debs is the cute ass you'd marry and have raise your kids.
Everyone's a winner!
I wouldn't pull out of either of them! I would love to creampie both of them. God! I would love to watch my cum ooze out of tiffany's redhaired pussy. Man!
wow i love debbie gibson but i would do all kinds of thigs to tiffany
Tiffany looks like a grade c stripper who hangs out at a freak show in her spare time.while Debbie looks far more sophesticated and real (airbrushign aside that is). Definatly Debbie all the way.
If they had done this when they were 18 I'd be interested.
Tiffany at least showed us her pussy! She's got to be the winner.
Debbie all the way. Just look at her ass and look at Tiffanys. Debbie has a great ass and a perfect body.
Tiffany all the way.... I have a thing (all 11 inches) for redheads with nice boobs... but I would not argue about a night with deb cause she's cute too...
I got to say, I've never cared to much for red heads but
DAM!!!! Tiffany gives me a bone. I would do them both,
Tiffany can take a ride on my bone and at the sametime Deb could sit on my face. And they could swich anytime they wanted to. Oh fuck I love the thought of that!!!
I am a CRAZY sucker for the redheads, so Tif was definitely my choice in the 80's when they were young. However, I am an ass man and like the small boobs, and Deb has a MUCH prettier face , so from these pics...........Debbie by a landslide.
ALWAYS loved Debbie Gibson, and i would pick her first. Although i would surely FUCK either one of them
i think they are both equally hot as hell and would love a threesome.
oh yeah i forgot to mention that i met them both in early 1988 and would have loved a threesome back then too.
That's a tough one for sure. I was totally in love with Debbie in the 80's(well, in lust anyway) and she's obviously way more talented as a performer. Plus, she keeps herself in amazing shape. However.....
Gotta love those nice big tits on Tiffany! I don't really wanna choose, but I'd pick Tiffany's body over Debbie's. I'll take them both though!!
Tiffany showed bush, Debbie did not.
Game. Set. Match.
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