Kimora Lee Simmons

When Simmons was 17, and still working on finishing up high school, she met 35-year-old hip-hop entrepreneur Russell Simmons. He had become smitten with the six-foot-tall Simmons after seeing her on the runway during New York City's Fashion Week and had sent the young model a bouquet of flowers so large that it took two men to carry. She was impressed, but Banks, who had also received flowers from the mogul, initially warned Simmons to forget him for he was a self-professed and well-known womanizer and playboy.

Russell Simmons, once a New York City street hustler, had risen to the height of fame and fortune as the godfather of the hip-hop movement. He founded the Def Jam record label in 1984, which released the work of such influential artists and groups as Run-D.M.C., LL Cool J, Slick Rick, Public Enemy, and the Beastie Boys. In 1991 HBO's Def Jam Comedy Hour became a forum for black comedians including Martin Lawrence, Chris Rock, Jamie Foxx, Steve Harvey, and Bernie Mac. In 1992 he created Phat Farm, which became a successful men's clothing line featuring hip fashions for the urban male.

Despite her friend's warning, Simmons allowed her suitor to pursue her, but his roaming ways strained the relationship, which was on-again, off-again for several years. When Simmons retreated to Milan, Russell Simmons took up yoga and reformed his lifestyle to the straight-and-narrow, and eventually convinced Simmons's mother to give him her daughter's phone number in Italy. Reconciling with her reformed king of hip hop, Simmons moved in to Russell's Beverly Hills home and attended classes at UCLA. With the relationship now on solid footing, in 1998 the couple were wed on the Caribbean island of St. Bart, vowing before a gathering of entertainment, music, and fashion elites to stay together "for richer or richer." The service was performed by Russell Simmons's brother, Pentecostal minister and rapper Joey "Rev Run" of Run-D.M.C. The elaborate reception was held on a 190-foot yacht.