Chris Brown's Halloween Jihad

When: October 2012

Chris Brown has had plenty of ridiculous outfits in the past—some of which are not costumes—but this year’s takes the cake. The singer showed up with full entourage in tow to Rihanna’s Halloween party all dressed up as terrorists. There are five of them and not one thought this would be totally fucked up? He tried to defend his costume, but he came off unapologetic and upset at his critics. Breezy, who racked up a few controversial moments this year, clearly hasn’t perfected the art of damage control.