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

Welcome, celebrity gossip fans, to The Hollywood Gossip Caption Contest, a Friday tradition, now in its 69th week. Who won this week's Caption Contest?

This week's pic - featuring Miley Cyrus, Taylor Swift and Katy Perry - inspired some good captions. Our winner is bradas. Congrats! Thanks to all for playing!

Taylor Swift, Miley Cyrus and Katy Perry

"Let's all have a quick pic!" Looks like Katy took it the wrong way!