2. Jessica Simpson
There are two reports of romps with pretty blonde celeb Jessica Simpson: one in 2004 and again in 2006. With voluptuous curves and bubbly personality, Levine just had to go back for more. Simpson started out as a singer, but quickly moved on to find fame on reality TV. Then she dabbled with film, as sultry Daisy in the Dukes of Hazzard. But what really put butter on her bread is her clothing line. The Jessica Simpson Collection is the first celebrity clothing line to reach one billion dollars in sales. Years after her time with Levine, the starlet has settled down with a family of her own.
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