by Free Britney at . Comments

Welcome, all you celebrity gossip and Hollywood news readers across the globe, to The Hollywood Gossip Caption Contest, a Friday tradition.

Who who this week's contest, featuring porn star Jenna Jameson and boyfriend, UFC badass and Celebrity Apprentice star Tito Ortiz? Let's find out.

Jenna Jameson Naked

It was a tough call, but we picked Kelly Belly as the winner. Woo! The winning caption appears beneath the photo. Scroll down for the full list of entries!

Thanks for playing and good luck again this week!

Jenna: I'm a virgin, Tito.

by Free Britney at . Comments

Welcome back, celeb gossip and Hollywood news readers across the globe, to The Hollywood Gossip Caption Contest, a Friday tradition and fan-favorite.

Who won this version of the contest, featuring the fashion-impaired, increasingly troll-like Olsen Twins? It was a tough call, but we chose Stephanie!

Nate Lowman Picture

The winning entry appears beneath the photo. Scroll down the page for the full list of replies, and good luck again in this week's all-new Caption Contest!

Mary-Kate: "Help Ashley my hand is stuck in this position from holding a Starbucks cup for so long."
Ashley: "Thats okay, your hand is the least of your worries."

by Free Britney at . Comments

Welcome back, celeb news and gossip readers around the world, to The Hollywood Gossip Caption Contest, our weekly fan-favorite tradition.

Who won this week's contest, featuring the always-skanky (but entertaining) Paris Hilton? It was a very tough race, but we've settled on the winner.

Ready to Party

Congratulations to Debra Walker for a terrific entry. The winning caption appears beneath the photo. Scroll down for the full list of captions we received.

Good luck in the next edition of The Hollywood Gossip Caption Contest!

Clearly missing Science Day at school, Paris mistakes cm for inches when ordering her Village People Tribute outfit.

by Free Britney at . Comments

Welcome back, entertainment news and celebrity gossip fans around the world, to The Hollywood Gossip Caption Contest, our Friday afternoon tradition.

Who won this week's contest, featuring a pregnant Jamie Lynn Spears? It was a tough call, since we received record responses, but we've chosen a winner.

Cute Jamie Lynn Spears Picture

This week's Hollywood Gossip Caption Contest winner is Kellie G. Nice work! Just scroll down to read the full list of replies (and the winner, beneath the photo).

Boy, I wish I would've kept my feet on the ground instead of in the air.

by Free Britney at . Comments

Welcome back, entertainment news and celebrity gossip fans around the world, to The Hollywood Gossip Caption Contest, our Friday afternoon tradition.

Who won this week's edition of the contest, featuring Lauren Conrad (LC), Lauren Bosworth (Lo) and Stephen Colletti? Let's take a look!

LC in Blue

Honorable mention goes to jschmoke (great Brody Jenner / Frankie Delgado idea), but this week's champion is Kelly. Congratulations to the winner!

The winning entry appears beneath the photo below. Scroll down for the full list of captions we received! A lot of them are really quite good.

Thanks for playing and good luck again this week!

Announcer: "And now, the world premiere of Heidi Montag's video of 'Higher.'"
Lo, LC, Stephen (and the other 19,997 in attendance): HAHAHAHAHAHA!

by Free Britney at . Comments

We welcome you back, celebrity gossip and news fans around the world, to The Hollywood Gossip Caption Contest. This week's edition, featuring girl on girl action heroes Paris Hilton and Elisha Cuthbert, got some great replies.

We liked a lot of the captions, but chose Katie as the winner. Scroll down to read the winning entry (under the photo) as well as the full list of submissions. Thanks for playing and good luck again in this week's new Caption Contest!

Paris, Again

Elisha: "Paris, it doesn't matter how much I zoom in, it's still gonna look like you're holding a rat."

by Free Britney at . Comments

We welcome you back, celebrity gossip fans around the world, to The Hollywood Gossip Caption Contest, a Fun Friday afternoon tradition.

This week's winner is Historygirl. Congratulations! It was a tough choice, but no way we could pass up any reference to the great Blake Fielder-Civil.

Conservator and Daughter

The winning caption to this classic, pre-hospitalized Britney Spears photo appears below. Thanks to all for playing and good luck again this week!

Brit: Hey Blake, let's get together sometime, who cares about Amy!
Blake: Sorry, I have to hang up, it's time for yard exercise.

by Free Britney at . Comments

We welcome you, celebrity news fans around the world, to The Hollywood Gossip Caption Contest. This week's winner: lucy lesbian. Congratulations!

The winning reply appears below the pic. Scroll down the page to read the full list of (hilarious) captions we received. Please come back and play every week!

Hillary Clinton and Sarah Palin Texting


Oh look, there's someone Bill hasn't f***ed.

by Free Britney at . Comments

We welcome you, celebrity news fans around the world, to The Hollywood Gossip Caption Contest. This week's winner: smart ass. Congratulations!

The winning reply appears below the picture. Scroll down the page to read the complete list of (hilarious) captions we received. Good luck again this week!

Totally Capable

Boys!! Boys!! Ya'll stop that cryin'. Mommas fine. She's just havin' a cuckoo for cocoa puffs moment. Look at all theses nice men that have come to take me to the market to get us some moo-cow and cereal". I think I'm gonna cry. No, I think I'm gonna laugh. No, I think I'm gonna sing a song for ya'll. How about "Crazy Train" by Ozzy Osbourne. Wait, this ain't no train it's an ambulance. Where ya'll takin' me... wait! I'm Britney bitch!

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