The Most Awkward Photos Of Celebrities With Playboy Playmates

Whether they’re Bunnies, Playmates or just models, celebrities loooove hanging out with the women of Playboy.

1. Stephen Dorf

Why so serious bro, it’s a party.

Image by Michael Buckner / Getty Images

2. Lil Jon

That’s So Lil Jon.

Image by Evan Agostini / Getty Images

3. Jeremy Shockey

Shockey feels the need to do something that will make it seem like he’s casual about this situation, so he pretends to be a Bunny too.

Image by Andrew H. Walker / Getty Images

4. Anna Faris

Never has it been more clear that even if you have pretended to be a Playmate, you are not actually one.

Image by Jamie McCarthy / Getty Images

5. Tinsley Mortimer and then-boyfriend Brian Mazza

Tinsley has her normal Tinsley face on, but Brian’s trying so hard to be nonchalant about this encounter that he’s focusing so. carefully.

Image by Joe Kohen / Getty Images

6. Former NFL player Warren Moon

He’s got Skinny Water to help get him through this experience.

Image by Joey Foley / Getty Images

7. Adrianne Curry

The one time Adrianne Curry was actually more clothed than her companions.

Image by Alberto E. Rodriguez / Getty Images

8. Tom Arnold

*SMILES*

Image by Neilson Barnard/ / Getty Images

9. Ultimate fighter “Rampage”

Dear god.

Image by Steve Mack / Getty Images

10. Dave Annable

Just a regular guy, standing here with his arms around two beautiful ladies, feeling fine, with eyes VERY wide open.

Image by Stephen Lovekin / Getty Images

11. Daniel Dae Kim

He’s totally unfazed but can’t control that mild smirk.

Image by Jamie McCarthy / Getty Images

12. Montel Williams and his wife

Montel suggested to his wife that they jam ourselves in the middle of this pack of Playboy models for a hot second and she readily agreed, with a pained smiled.

Image by Joe Kohen / Getty Images

13. David Burtka

There are no words for this photo except that David Burtka wins at life.

Image by Andrew H. Walker / Getty Images

14. Snoop Dogg

This is really just his preferred state of being.

Image by Jamie McCarthy / Getty Images

See?

Image by Craig Barritt / Getty Images

16. David Arquette

Utterly casual.

Image by Andrew H. Walker / Getty Images

Seriously, so relaxed.

Image by Jamie McCarthy / Getty Images

If he was getting paid for this, his life would be perfect.

Image by Jamie McCarthy / Getty Images

19. BONUS: Janice Dickinson

She was the first Supermodel, and don’t you forget it.

Image by Alberto E. Rodriguez/ / Getty Images