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.
You may like
Get The Essence Newsletter and Special Offers delivered to your inbox!