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Celebrities have so many eligible bachelors to choose from, and the pickings in Hollywood are anything but slim with young cuties like Nick Jonas and Liam Hemsworth wandering around without someone else to hold their hands—we’d gladly volunteer, BTW!

Yet, despite the obvious overflow of eye-candy in their own social circle, all of the bachelorettes on this list have always had their eyes fixed on older men—even if it was under somewhat-illegal circumstances.

The Baby Phat founder married into hip-hop royalty by tying the knot with Russell Simmons in 1998.

Eleven years and two children later, she and Simmons, who’s almost two decades older than the long-legged model, divorced.

List of Famous Men Who Married Much Younger Women, loosely ranked by fame and popularity.

WENNSome people have a preference when it comes to picking a mate and Kimora Lee Simmons is certainly one of them.Soon she moved on to Djimon Hounsou, who’s only a mere 14 years older than her.But after five years and a son together, they split up and she moved on to investment banker Tim Leissner whom you can tell has at least a few years on Kimmie.WENNHayden Panattiere’s first big role was on a soap opera but she grabbed Tinsel Town’s attention as the indestructible cheerleader on the hit show “Heroes.” She also found herself in love with her co-star Milo Ventimiglia.Their relationship sparked a controversy because she was just 17 at the time while he was almost 30.

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