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Rewinding the Country Charts: In 2008, Jessica Simpson Crossed Over to Country

The pop star debuted at No. 1 on Top Country Albums with "Do You Know."

After starring in an MTV reality show – Newlyweds: Nick and Jessica, with then-husband Nick Lachey – and in the big screen remake of The Dukes of Hazzard (as Daisy Duke, naturally), pop star Jessica Simpson set her sights on the country charts.

On Sept. 27, 2008, Simpson’s lone country set, Do You Know, debuted at No. 1 on Billboard‘s Top Country Albums tally. The LP yielded the top 20 Hot Country Songs hit “Come on Over,” while Dolly Parton wrote and sang harmonies on the title track. Simpson subsequently opened for Rascal Flatts on tour in 2009.

Prior to her foray to Nashville, Simpson scored six top 20 pop hits on the Billboard Hot 100, led by her breakthrough, the No. 3-peaking “I Wanna Love You Forever” in 1999. In 2004 “With You” topped the Pop Songs airplay chart, while in 2005 she reached No. 14 on the Hot 100 with the Dukes soundtrack single, and Nancy Sinatra remake, “These Boots Are Made for Walkin’.”

Simpson, 38, has also built a reputation as a business mogul and fashion designer. In 2016, she sold her majority share of the clothing line The Jessica Simpson Collection, which, at the time, Forbes reported was bringing in $1 billion annually.