Jessica Simpson rose to fame in the late 1990s thanks to her singing chops. She scored a reality TV show with her then hubby Nick Lachey, divorced, went country, and found love again with Cowboys quarterback Tony Romo, who reportedly ended their one-and-a-half-year relationship on the eve of her 29th birthday. It seems her baby sister has had more luck in the love department. (Photo by Getty Images)
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