The Best Songs by Taylor Swift

Taylor Swift is a cultural touchstone for millions of people. The young singer-songwriter has captured the hearts of an entire generation. Her music has evolved from the country romance of her teens to the imperial pop of her twenties to the ambivalent ruminations of her thirties. Her sonic evolution has mirrored that of the millennial baby boom, and it’s a fitting metaphor for a generation coming into its own.

At an industry showcase at Nashville’s Bluebird Cafe in 2005, Swift caught the attention of Scott Borchetta, a Dreamworks Records executive who was preparing to launch his independent label Big Machine Records. Swift was one of the first signings and would remain with the label for over a decade.

In the early days, Swift penned songs for other artists including Boys Like Girls and Kellie Pickler and wrote 2 tracks for Disney Channel’s Hannah Montana. She also started her own publishing company and toured extensively across the US.

On her second album, Fearless, Swift expanded her musical palette by incorporating rock and electronic influences into her pop. The result was an album that broke several records and became the best-selling female artist’s debut in history.

Swift’s fifth album, 1989, marked her reintroduction as a pop musician. The album topped the Billboard 200 and sold over 1 million copies in its first week. Swift teamed up with new producers and songwriters on the record, and her new sound excited fans.

A mournful tribute to a lost friend, this song is an evocative reminder of how personal her work remains. Its lyrics evoke the kind of grief that permeates so many of Swift’s best songs, a mix of wistful memories and a nod to private tragedies that most of us will never know about.

This is a classic example of Taylor’s ability to capture the way that women think and feel. The sentiments may seem a little overblown, but it’s hard to argue with the power of this song.

In a career filled with highs and lows, Taylor arguably reached her pinnacle with the release of her seventh album, Reputation. It was a commercial and critical smash, spawning three top five singles, and won Taylor her third Grammy and four American Music Awards in 2019. The album went on to sell over 3 million copies in its first week, making it the fastest-selling album of 2022.

Following the success of Reputation, Taylor teamed up with producer Jack Antonoff on her eighth studio album, folklore. The album continued to incorporate a variety of genres and featured collaborations with Bon Iver’s Aaron Dessner, Jack White on “Blank Space”, The National’s Colin Meloy on “Folklore” and HAIM on “Willow”. Both folklore and its lead single, “willow”, debuted at number one on the US Billboard Hot 100 and Billboard 200 charts, respectively, becoming the first act in music history to have two albums chart at the top of both lists simultaneously. The album also topped the Streaming Chart and Digital Albums Chart in the US.