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. They just choose to express it in different ways.

1. Stephen Dorf

Michael Buckner / Getty Images

Why so serious bro, it’s a party.

ID: 973692

2. Lil Jon

Evan Agostini / Getty Images

That’s So Lil Jon.

ID: 973774

3. Jeremy Shockey

Andrew H. Walker / Getty Images

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.

ID: 973892

4. Anna Faris

Jamie McCarthy / Getty Images

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

ID: 973906

5. Tinsley Mortimer and then-boyfriend Brian Mazza

Joe Kohen / Getty Images

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.

ID: 973821

6. Former NFL player Warren Moon

Joey Foley / Getty Images

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

ID: 974011

7. Adrianne Curry

Alberto E. Rodriguez / Getty Images

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

ID: 973833

8. Tom Arnold

Neilson Barnard/ / Getty Images


ID: 973926

9. Ultimate fighter “Rampage”

Steve Mack / Getty Images

Dear god.

ID: 974012

10. Dave Annable

Stephen Lovekin / Getty Images

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

ID: 973863

11. Daniel Dae Kim

Jamie McCarthy / Getty Images

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

ID: 973944

12. Montel Williams and his wife

Joe Kohen / Getty Images

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.

ID: 974016

13. David Burtka

Andrew H. Walker / Getty Images

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

ID: 973886

14. Snoop Dogg

Jamie McCarthy / Getty Images

This is really just his preferred state of being.

ID: 973946
Craig Barritt / Getty Images


ID: 974010

16. David Arquette

Andrew H. Walker / Getty Images

Utterly casual.

ID: 973909
Jamie McCarthy / Getty Images

Seriously, so relaxed.

ID: 973882
Jamie McCarthy / Getty Images

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

ID: 973875

19. BONUS: Janice Dickinson

Alberto E. Rodriguez/ / Getty Images

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

ID: 973857

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