by Free Britney at . Comments

It was a Caption Contest waiting to happen.

From the moment Taylor Swift released "Dear John," her latest single and thinly-veiled John Mayer condemnation, the floodgates opened. But who won?

On the Guitar

That distinction goes out to Emma, with honorable mentions going to Nicole Frett, Leo and Bev. The winning entry appears below. Thanks for playing!

I hereby pronounce you "Sir Douchebag."

by Free Britney at . Comments

Welcome to another edition of The Hollywood Gossip Caption Contest!

As we discussed Tuesday, Taylor Swift's new single, "Dear John," seems to take some thinly-veiled shots at John Mayer. Sounds like Caption Contest material to us!

Taylor Swift on Stage

Just come up with the best caption(s) for this photo, click "Comments" and fire away. Leave one. Leave 10. We'll announce a winner tomorrow. Go to town ...

by Free Britney at . Comments

Friday's edition of The Hollywood Gossip Caption Contest tasked our readers with writing the best caption for this picture of John Mayer balling.

Our winner is Ted Binion. Congratulations!

The selected caption, particularly topical in light of the Spencer Pratt sex tape scandal, appears below. Thanks to everyone, as always, who sent in caption(s) and best of luck again next time in The Hollywood Gossip Caption Contest!

John Mayer Balls

This must be what Heidi Montag's breasts feel like.

by Free Britney at . Comments

Welcome to another edition of The Hollywood Gossip Caption Contest!

It's easy and fun to play: Just come up with the best caption(s) for the photo below! Our subject this week: John Mayer ballin' ... on the b-ball court that is.

What could he be saying or thinking? You tell us. Give it your best shot by leaving a comment or 10. We'll announce the winner Monday. Good luck ...

John Mayer Balls

by Free Britney at . Comments

Welcome, celebrity gossip fans, to The Hollywood Gossip Caption Contest, a Friday tradition, now in its 60th week. Who won this week's Caption Contest?

When John Mayer points at a Marley & Me poster, the material is endless. We chose the entry sent in by NotAJohnMayerFan as the winner. Congratulations ...

If John got the leading role instead of Owen, the movie would be called Douchebag and Me.

John Mayer Biography

John Mayer With Long Hair John Mayer is a singer, songwriter, guitar player and Grade A douchebag hailing from Connecticut. The cheesy musician has become a major... More »
Born
Birthplace
Bridgeport, Connecticut
Full Name
John Clayton Mayer

John Mayer Quotes

The feathered cut projects an attitude of ease and quiet confidence that seems to have all but eluded our generation. This is a work in progress, and as my hair grows longer it will serve to become a more stirring and poignant statement.

John Mayer [on haircut]

To adults who will vote for him, Barack Obama represents a return to prosperity. To the youth, he represents an introduction to it.

John Mayer
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