Best Breakup - 2009
Tony Romo and Jessica Simpson
OK, we'll forgive you if you spent about a week thinking Cowboys quarterback Tony Romo's All-American romance with local pop princess Jessica Simpson was adorably appropriate. After all, why wouldn't America's hot-and-ditzy princess want in on a little career Romomentum? But after the infamous pink jersey loss and the disappointments that followed, was there anyone in town besides bloggers hard-up for material who really wanted to see the couple last? Honestly, we're glad to see Romo's taken to an Entourage-like, Afflicton-attired existence. Sure, he's douche-y and less likable now, but when it comes to Cowboys football, we don't mind a little bros philosophy.