Taylor Swift is the most popular singer in pop history, and her enduring career has made her an emblem for the millennial generation. She rose to fame in the early 2000s, just as the teen zeitgeist shifted from suburban romance to imperial pop to ambivalent ruminations about growing up. The songs on this list span her career, from the twee country romps of her teens to the post-dramatic breakup ballads of her twenties and beyond. They also chronicle the evolution of a star whose musical style has adapted to the shifting cultural climate of her audience, spanning genres from rock to R&B to dance-pop to electronica.
At an industry showcase at Nashville’s Bluebird Cafe in 2005, Swift caught the attention of Scott Borchetta, a record executive who was preparing to form his independent label Big Machine Records. Her father purchased a three percent share of the company, and Swift became one of its first signings. During her time at Big Machine, she wrote and performed many of the songs that would eventually appear on her debut album, Speak Now, including “Tim McGraw.”
As a member of the millennial generation, Swift has never seemed particularly concerned with maintaining a traditional image. She has embraced her status as a global icon, and has used it to her advantage in the realm of fashion, where she has often led the way. She has embraced her image as a sexy, smart, talented rebel with a cause and has pushed back against the idea that she is a victim of the media.
Although she has ascended to pop royalty, Swift’s roots remain deeply planted in country music. She has deftly traversed the genres of country, pop, and adult alternative with an unerring sense of style. On this winning deep cut, she stretches her vocal range to include an Imogen Heap-style yawp, and producer Nathan Chapman brings out all of the tricks in the Nashville book (including compressed hip hop drums).
After an extended period away from the spotlight, Swift resurfaced in 2016 with a blockbuster album that pushed every button for her core audience. The success of Reputation shattered records, including the fastest-selling album in US chart history. The single from this project, Look What You Made Me Do, was the most watched video on YouTube in 24 hours and broke several social-media records. It was also her fourth consecutive number one on the Billboard Hot 100, a feat that no other artist has accomplished. For millions of fans, this song and the album that followed it signaled a rebirth in Swift’s career. She has continued to reinvent herself with each new release, navigating the worlds of pop, country, and even rap with ease. She has also proved that pop can accommodate a wide range of melodic styles and lyrical themes, proving that it is not simply the sexiest genre in town.
