The Hollywood Gossip Caption Contest 55

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Welcome, celebrity news fans everywhere, to The Hollywood Gossip Caption Contest, our Friday tradition. Who won the Caption Contest this week?

When Britney Spears and Madonna get together, the funny captions are not in short supply. We chose cutieshortie2005 as this week's champion.

Congratulations! The winning entry appears beneath the photo. Thanks to all for playing and good luck again in the Caption Contest this week!

Britney and Madonna

You only got 4 minutes to get Madonna some pants!

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Britney - You have 4 minutes to finish clowning around on stage Madonna!


Scary and Junior Scary.


You only got 4 minutes to get Madonna some pants!


Brit... Thank god your Dad is in charge of you or this could be you when you are 50 (and think you are 25)!!!


Guess Madonna still thinks it's Halloween!


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Britney - Man we're bad at kareoke!
Madonna - Shut up, im rocking this joint!


madonna: come on over here and look at my tight thighs. give me a kiss britt
britney: i was hoping wearing more clothes this time would keep you away from kissing me.


Hey ya'll, would it still be hot if I kissed Madonna or just kinda gross now?