Usher's Former Flames

Usher's Former Flames
ESSENCE.COM Aug, 27, 2008

1 of 4 Jim Spellman/WireImage.com

Usher and Chilli at Mercedes-Benz Fashion Week in New York City in 2002.

2 of 4 Jean-Paul Aussenard/WireImage.com

In 2003, Usher celebrated his 25th birthday in costume with then-girlfriend Chilli in West Hollywood, CA.

3 of 4 REUTERS/Dylan Martinez

Naomi Campbell accompanied Usher to the MTV Europe Music Awards back in 2004.

4 of 4 Djamilla Rosa Cochran/WireImage.com

Usher and former red-carpet companion and model, Eishia Brightwell, at Russell Simmons’ East Hampton Estate in 2005.