Why Do I Feel Funny?

With the recent leak of the cover, I have been feverishly thinking (Not that way, sick brains!) about Lindsay Lohan's soon to be released Playboy issue. I mean, there is a lot of potential for awkwardness. It had to be re-shot, so what kind of crap was produced in the first go-round? Was this pre or post fixing the meth teeth? I can't remember, and I'm too freaking lazy to google it. Am I on meth?

Anyway, all of this got me thinking about celebrities posing for Playboy or simply being on the cover. There have been a lot. Some good, some bad, some that are just...awkward. So here's my list of the top five most awkward celebrity Playboy cover models and/or pictorials.

Honorable (or horrible) Mention: Shannen Doherty in German (???) Playboy

What in the hell IS this? Nobody does this to Brenda Walsh's face! This mess looks like it was painted by a blind monk that worked as Kelly Taylor dictated. Hell to the naw! (Copyright: Whitney Houston)

# 5 Teri Polo

I personally enjoy my Teri Polo starring alongside the likes of Ben Stiller and Robert De Niro in family friendly-ish films, not attempting to mouth love a strawberry and showing me her hootenanny. No ma'am.

# 4 Carnie Wilson, Tiffany, and Debbie Gibson (TIE!)

I can declare a tie! Shut your mouth. Don't get me wrong, they all looked great for their a-hem "spreads" (I'm sorry, gross.), but this is how I like and picture my Carnie, Tiffany, and Debbie (I'm not calling you Debrah) Gibson.

Now THIS is glamor, okay Carnie? Tell me you can tear your eyes away from those earrings. I dare you!

Can't you just SMELL the Electric Youth perfume wafting from this photo? And that hat? It beats boobs any day, any time.

 

Speaking of hats, can you even with this? Because I sure as hell can! This picture is what happens when a festive Christmas wreath marries a door knocker and births a ginger angel.

# 3 Latoya Jackson

We all know that Toy Toy is the cray cray of the Jackson clan (which is really saying something), but on the real I can't even mess with this cover. Between the studded jacket, those nails, and the glitter star earring that's bigger than her face, I can't even hate on this magical carpet ride.

# 2 Donald Trump

Why? And...No.

# 1 Candice Bergen

This is like finding a video of your parents doing it. Just a whole big ol' bag of no. What would Murphy Brown say about this? I would rather see Miles and the painter/handyman/whatever that dude did in a warm embrace than this. (I want to see that anyway.)

At least she didn't get nakey. That's something her shoulder pads could never unsee. Pin It