Gallery - Gone Country 4 of 15

Jessica Simpson

Image courtesy of Jeffery Mayer / WireImage

When pop princess and entertainment mogul Jessica Simpson made the jump to country, people were skeptical about her loyalty to the genre.  However, Jessica's debut country single "Come On Over" from her 2008 album Do You Know seem to do well.  Unfortunately for her, it was all downhill from there as the next two singles didn't even make it to the Top 40.

 

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