So what's a hot Hollywood star to do when he's fresh out of a relationship? How about hook up with a supermodel? Hey, that's what Usher did in 2004 after his split with Chilli. He first hooked up with Naomi at the MTV Video Music Awards in August 2004 and the couple heated up quickly. That October, Naomi threw Usher a party for his 26th birthday, and the couple spent Thanksgiving together at Usher's mom's house in Alpharetta, Ga., in November. But did you really think sweet Usher and phone-throwing Naomi would stay together forever? The following year, Usher moved on to model Eishia Brightwell.