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The compilation opens up with Wilson's signature hit and number one country hit "Redneck Woman", from her debut album Here for the Party (2004). The next song to follow up is the title track, which was a top three hit on the Hot Country Songs chart (then known as "Hot Country Singles & Tracks"). "Homewrecker" follows after, which peaked at number two. "When I Think About Cheatin'", one of the four top five hits from Here for the Party, is the final single included from the album.
"California Girls" is the song that follows after, which was the final single from her sophomore album All Jacked Up (2005). The Merle Haggard duet "Politically Uncorrect" is next, which is also the first song in Greatest Hits that Wilson did not co-wrote. After is "I Don't Feel Like Loving You Today", which was Wilson's first single to miss the top ten on the country charts.
"One of the Boys" is one of two tracks from her 2007 album of the same name included on Greatest Hits. "Come to Bed", a duet with frequent collaborator John Rich, was the other included. Both singles barely scraped into the top 40 at country radio. The final previously released song from the compilation is "All Jacked Up", the title track to All Jacked Up, which is noted for its record-breaking debut at number 21 on Hot Country Songs when it debuted. The final song and only new song included on Greatest Hits is a live version of "Barracuda" by rock band Heart, which Wilson has performed a few times. The only single excluded from the compilation is "You Don't Have to Go Home" from One of the Boys, which was Wilson's only single at the time of its release to miss the top forty.
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