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The Song: "Tim McGraw"
The Deets: This track — Swift's first-ever single off her eponymously titled album — was released on June 19, 2006. It took more than six months for it to climb its way to a peak position on the Billboard charts, at No. 40. Breaking into the top 50 as a new artist isn't exactly NBD, and the success primed Swift for future breakthrough hits.
On A Scale Of Pop To Country: So frigging country.
The Song: "Change"
The Deets: Off Swift's second album, Fearless, "Change" represents the singer's first top 10 hit. It peaked at No. 10 on August 30, 2008.
On A Scale Of Pop To Country: Not named after a country singer. But still pretty country.
The Song: "Love Story"
The Deets: If you listened closely back in the late aughts, this song was playing on pretty much every teenage girl's earbuds in America. Also from the Fearless album, "Love Story" peaked at No. 4 on the Billboard charts on January 17, 2009. It became the second-best-selling country single of all time.
On A Scale Of Pop To Country: Still country. But sneaking into crossover territory. This one received a lot of radio play on pop stations.
The Song: "You Belong With Me"
The Deets: Along with "Love Story," this song tipped Fearless into the best-selling record of 2009 and helped Swift take home four Grammy Awards — making her the youngest-ever winner of Album of the Year.
On A Scale Of Pop To Country: Slightly less country. Slightly more pop. Perfectly positioned to make a leap.
The Song: "Back to December"
The Deets: True Swifties will remember this track fondly, though the rest of us might not have it burned into our brains. But "Back to December," which peaked at No. 6 on the Billboard charts on October 30, 2010, helped push Swift's third album, Speak Now, to No. 1 on the Billboard 200 top releases chart.
On A Scale Of Pop To Country: This is a country backslide. But still Swiftilicious, obviously.