After a successful period which spawned five country number one hits and two platinum albums, Burn (2000) and I'm Alright (1998), Messina took a break from the music industry and released a Christmas album titled A Joyful Noise (2002). The compilation includes eleven of Messina's country hits. Included on Greatest Hits is four new tracks: "Was That My Life", "I Wish", a cover of the Jessica Andrews song "Wishing Well", and "You Belong in the Sun", with "Was That My Life" and "I Wish" becoming singles, peaking at number 21 and 15 on the BillboardHot Country Songs chart.
The compilation became a success, becoming her second number one album on the Top Country Albums chart following Burn and was Messina's then highest-charting entry on the Billboard 200, debuting at number 14. The album was later certified Gold by the RIAA for shipments of 500,000 copies. The Enhanced CD version of the album includes the video for "Bring On the Rain".
Greatest Hits debuted at number one on the Top Country Albums chart for the week of June 6, 2003, debuting with first-week sales of 52,000 copies.[3] The album gave Messina her second number one album on the country charts after Burn (2000). Greatest Hits also became Messina's then highest charting on the Billboard 200, debuting at number 14; her 2005 album Delicious Surprise would later surpass it when it debuted at number seven.[4] The next week, Greatest Hits fell to numbers two and 35 on the country albums and Billboard 200; in total, the album would spend 83 weeks on Top Country Albums and 20 weeks on the Billboard 200.