Music career 1996–97: Country success Messina released her self-titled debut album in 1996. It spawned two top-10 hits, starting with the lead single, "Heads Carolina, Tails California", which peaked at number two on the country charts and its follow-up, "You're Not in Kansas Anymore" gained similar success. However, the two additional singles released from the album, "Do You Wanna Make Something of It" and "He'd Never Seen Julie Cry" peaked outside the country top 40 and were minor hits between 1996 and 1997. Following her major success, Messina performed 215 shows in 1996 and became one of the most successful new female vocalists of the 1990s. Her debut album sold over 500,000 copies and was certified gold by the RIAA. Messina's finances suffered due to a series of poor business decisions and a change of management that led her to nearly declaring bankruptcy; she nearly lost her home and her car. She spent nearly a year trying to write new songs and material for a new album that could help bring herself out of bankruptcy. She credited the radio success of "Bye, Bye" and "I'm Alright" with giving her a "second chance". 1998−2006: Breakthrough success Messina released her second album in 1998, I'm Alright. The album spawned three number-one hit singles on the Billboard Country Chart that year: "Bye, Bye"; "I'm Alright"; and "Stand Beside Me", all three of which charted on the Billboard Hot 100, as well. The fourth single, "Lesson in Leavin", was a cover of Dottie West's 1980 number-one country hit. The song peaked at number two for seven weeks. In 1999, she had another top-10 hit from the album, "Because You Love Me", which peaked at number eight on the Billboard Country Chart. In 2000, Messina received the Country Music Association's Horizon Award, which is awarded to new country music artists. She also won the Billboard "Most Played Female at Country Radio", and won three major awards from the Boston Music Awards, located in her home state of Massachusetts. Messina's album became her biggest-selling album to date, selling over two million copies in the US, receiving an RIAA certification of double platinum. She released her third studio album, Burn in 2000, which aimed towards country pop-styled music. The album's lead single, "That's the Way" peaked at number one on the Billboard Country Chart and also became her highest-charting single on the Billboard Hot 100, peaking at