
I think that in comparison to the other pop artists of the late 90s / early 00s (Britney, Christina, Mandy Moore, or even Willa Ford) Jessica Simpson had the highest chance of going country. You knew she got a taste when she decided to butcher Nancy Sinatra’s “These Boots Are Made For Walking”. I really hoped that that was the last straw, but alas she keeps trying to come back into the spotlight.
It’s sad that there are only two big things I really remember her for, 1) The Chicken/Tuna debacle and 2) Divorcing Nick Lachey (who by the end of the show’s run I felt sorry for). Her music was very throwaway and her biggest hit (arguably) was “With You” which went 2x Platinum Thanks Wikipedia. Clearly she gained popularity from her MTV Show.

Does Jessica need another reality show to re-establish her career? Possibly. I wouldn’t mind seeing her as a contestant on Dancing With The Stars. Is her dad still her manager? He better pimp his daughter more.
Source for Album Sales
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