Taylor Swift is one of the most popular singer-songwriters of the early 21st century. Ans it’s been an incredible few years for the superstar. With each fresh release, the industry rejoices in the expectation of another market-defining sales boom; devoted fans seize on every sentence in her songs or a fresh interpretation of something they already love; and millions of others find simple comfort in powerful pop hits and her increasingly surprising output. Who would honestly have predicted her path from country protégé to pop powerhouse? We pick out the steps along the way with the best Taylor Swift songs.
30: Back To December
“Back To December” is one of the most tender ballads Taylor Swift has ever recorded. Its yearning elegance sadly saw it side-lined on many international charts, but Taylor’s US fans took the song to heart, lifting it to a No.6 Billboard peak and a respectable showing on the Adult Contemporary chart. It’s hard to believe that this confessional, knowing lyric was penned by a woman then barely in her 20s.
29: Love Story (Taylor’s Version)
The idea of an artist rerecording their back catalog as a means of re-establishing control isn’t entirely new, but Taylor Swift’s campaign to reassert control has taken the concept to a new level. In issuing a new version of her most recognized early hit “Love Story (Taylor’s Version),” she had a political point to make as much as a musical one. Taken from Fearless (Taylor’s Version) it topped country charts and featured many of the musicians from the original release. What makes it particularly interesting is the confidence of Taylor’s vocal and a confident mix that anchors that performance brilliantly.
28: Tim Mcgraw
While still at high school, Taylor Swift wrote ”Tim McGraw,” a tender ballad that plays to her belief that music offers the tonic to most of life’s ills. It’s a theme Taylor would return to many times in the years ahead, with the veteran country star’s music this time offering her the support she sought amid an early romantic crisis and providing inspiration for the song. It became the track the Big Machine label seized on when it signed the teenager when she was just 14. Co-written with long-term early collaborator Liz Rose, ”Tim McGraw” justified the label’s belief when it hit the stateside country charts in the summer of 2006, and even crossed over onto the US Billboard Hot 100, peaking at No.40 in an early hint of what the best Taylor Swift songs would be capable of.
After the edgier “Look What You Made Me Do” from Reputation, “Gorgeous” emerged as a midtempo ballad that harks back to a sweeter, more accessible Taylor Swift. Pop radio immediately embraced the Max Martin/Shellback collaboration and taken together both singles showcased Reputation as a bold, new canvass for Taylor’s stylistic diversity.
26: Safe And Sound
Launching in 2011, The Hunger Games was a huge international film franchise based on a trio of best-selling novels. Artists were clamoring to get their work onto the soundtracks, but Taylor’s rocky contribution, and one of her two soundtrack contributions, with “Safe And Sound,” recorded with alternative country act The Civil Wars, showed that Taylor was now finally starting to secure more favorable press.
25: Wildest Dreams
Following the high-octane power-pop of 1989’s initial releases, “Wildest Dreams,” promoted in August 2015, was a timely diversion into calmer waters. The ethereal dream-pop anthem, showcased in an Out Of Africa-inspired video co-starring Scott Eastwood, presented Taylor at her most seductive. It was another big hit and, in remixed form, became her first song to top the Billboard dance radio listings, proving that the best Taylor Smith songs can easily take her into new territory.
Pushed as Red’s second promotional single, the album’s title track was a return to her Nashville roots, dished up with a neat, contemporary pop twist. By this stage, Taylor was only really competing with herself on the country charts, and “Red” actually got stuck behind one of her own tracks near the top of the US Hot Country Songs listings.
When, just 18 months after the provocative Reputation, Taylor Swift emerged with another new song, “ME!,” it was a perfectly pitched step back in time: 60s-referencing bubblegum, anthemic 21st-century power-pop, and evergreen country that perfectly suited her. A contribution from Panic! At The Disco’s Brendon Urie added the ballast to rough up the sweeter top notes, which characterize all the obvious peaks of Taylor’s best songs. But it’s the clever blend that brings it all to life. Lyrically, “ME!” marked a return to familiar themes, but the styling was new and added considerable impact to a hook-heavy return to out-and-out traditional pop from Taylor. The pair’s performance at the 2019 Billboard Music Awards remains one of the show’s best openings to date.
22: Better Man
Written by Taylor Swift for the US group Little Big Town, and issued as a country chart-topping single in 2016, Taylor issued her own version of “Better Man” for the 2021 Red (Taylor’s Version) album as part of her campaign to re-establish the creative control of her earlier work. It’s a gloriously melodic gem that captures all the bittersweet emotion of the original. Red (Taylor’s Version) is a sizeable collection of spirited reimaginings and some intriguing songs lifted from material created during the original album project.
21: Everything Has Changed
It’s a sad reality that so many strong female icons still end up getting characterized by the men they may or may not be involved with. Taylor’s love life has generated an extraordinary – and frankly unwelcome – wider interest, but at least her relationship with Ed Sheeran was centered on the work they collaborated on. “Everything Has Changed” also appeared on Red and became a solo highlight of the album’s supporting tour. The artists’ vocal fit was indisputable, and the song became another major success, particularly in the UK, where it peaked at No.7.
20: The Man
This jagged, majestic pop cut is decorated with a synth-drenched chorus that became a worthy single from 2019’s Lover, which brought some lighter tone back to Taylor’s work after the confrontational Reputation. The video for “The Man” was a directorial debut for Taylor and led to her being the first woman to win Best Direction at the MTV Video Music Awards across its lengthy history.
19: Teardrops On My Guitar
This was Taylor Swift’s true breakthrough, hitting the Billboard Top 20 and becoming a live favorite. Though picking up the pace from “Tim McGraw,” “Teardrops On My Guitar”’s still-only-midtempo groove provided her first anthemic singalong and became a firm fixture in the star’s early live shows; the image of Taylor sparkling on stage in a shimmering dress and ubiquitous cowboy boots are forever associated with the track. Repackaged for international release, it became Taylor’s first UK hit (though it failed to dent the Top 40) and was the best performing single from her self-titled debut album.
18: The One
Opening 2020’s surprising Folklore, “The One” also raised eyebrows with its explicit lyrics but no one doubted this mellow track’s musical integrity. Folklore’s left-field folk-oriented turn from the pop temperament of Lover captured the word’s imagination in the earliest months of the COVID-19 pandemic, when life had also been turned so dramatically on its head. Issued as a single, “The One” made the Top 10 around the globe.
Internet leaks plague many artists, and Taylor Swift joined that unfortunate club when the lead track from her third studio album, Speak Now, sneaked online in the summer of 2010. Again supported by another strong promotional clip, later to be named the Country Music Television Video Of The Year, “Mine” was in many ways a subtle shift back towards her pure country roots. Like many of the best Taylor Swift songs, its charm lies in its steady melodic frame, even if, in hindsight, it seems its creator was perhaps considering a gear change to really lift her career to the next level.
16: Bad Blood
When a rumored remix of the 1989 album track “Bad Blood” turned out to be a collaboration with rapper Kendrick Lamar, many thought Taylor Swift was pushing things too far. For one thing, the lyrics of this song spoke frankly of an alleged business bust-up Taylor had experienced with another artist – which was a raw enough subject in itself – but the idea that America’s sweetheart would push her sound in a hip-hop direction seemed reckless to some. Taylor, of course, knew better and the track became the album’s third to top the US charts, while the high-concept superhero-inspired promo clip, packed with cameos, deservedly became MTV’s Video Of The Year.
Taylor Swift’s commitment to charitable causes is well documented and “Change” provides further early evidence of this. With all profits going to the US Olympic Team, it earns its place among the best Taylor Swift songs as her first Top 10 single in the States, “Change” drew on the familiar themes of empowerment and overcoming adversity but added a killer pop hook and an edgier rock riff to the mix. In hindsight, the signs of the artist Taylor was to become first started to shine through on this release.
Issued as the lead single for Taylor Swift’s eighth album, Folklore, “Cardigan”’s slow-burn melancholia was created by Taylor in partnership with project producer Aaron Dessner and became Taylor’s sixth chart-topper in her home country. Perhaps more of a performance piece than some of her more obviously autobiographical work, its hazy soft-rock balladry marks another high-mark in Taylor’s artistic journey, establishing her growing confidence across the genres.
13: You Need To Calm Down
On “You Need To Calm Down,” Taylor Swift reached the pinnacle of her pop career thus far. Cleverly referencing her tabloid story in the video – named clip of the year at the MTV Video Music Awards – she was directing the spotlight (that had at times threatened to blind her) back at us all instead. Of course, there’s something deeper happening in this hook-heavy genius too. Taylor has routinely used her platform for a generous range of issues, and this song speaks to the increasingly fractious culture of the 21st Century. Great artists entertain with a message, and Taylor has plenty to say on Lover’s indisputable highlight, which earned her a Grammy nomination for Best Pop Solo Performance.
12: Blank Space
By the time of 1989’s release, Taylor Swift was the master of the event video. “Blank Space” may forever be remembered for its classic high-camp promo clip, but the song stands up by itself, easily earning its place among the best Taylor Smith songs. Arch, knowing lyrics served with a dash of good humor powered this electro-pop track to the top of the Billboard charts and secured Taylor more nominations at the Grammy Awards, along with wins at the MTV Music Awards and American Music Awards.
11: Coney Island
The ninth track on Taylor Swift’s ninth album, “Coney Island” is among the most interesting of Taylor’s duets. Paired with vocalist Matt Berninger and his indie band The National, the kitchen-sink drama of its lyric is a terrific highlight of 2020’s Evermore. The National’s Aaron Dessner and his twin, Bryce, helped create this triumphant indie-rock that made a surprising choice for single release, even given Taylor’s increasingly devil-may-care attitude to those who still wanted a one-dimensional predictability to her work.
10: Shake It Off
If ever a song offered a literal as well as lyrical statement, “Shake It Off” was it. Ripping free from her country roots completely, “Shake It Off” was an out-and-out pop revolution for Taylor. The lead single from her 1989 album (named after the year in which she was born), it was a bold but still mainstream move that will forever be remembered as one of the best Taylor Swift songs of all time. The song’s throwback vibe marked a charismatic reinvention that rewarded Taylor with her biggest hit to date and a chart-topping position in her homeland. While maintaining her flair for creating melodies that worked across her growing range of audiences, “Shake It Off’ reinforced the mantra that the bravest artists always stay one step ahead of their audience’s expectations.
9: Look What You Made Me Do
When Right Said Fred got the call that their 1991 smash “I’m Too Sexy” had inspired part of Taylor Swift’s 2017 comeback, “Look What You Made Me Do,” they must have thought they’d won the lottery. Indeed, they probably did! The track smashed records around the globe and rewarded Taylor and co-writer Jack Antonoff, who also produced the song, with their first UK chart-topper. “The old Taylor is dead,” she told the world. It appeared the new one would do just fine…
8: You Belong With Me
Chosen as the third single from Taylor Swift’s second LP, Fearless, “You Belong With Me” was another anthemic, pop-flavored country track that became her biggest hit to date in the US when it peaked at No.2. Now increasingly confident in her video performances, Taylor’s styling – this time as the high-school sweetheart that other young women could still relate to – was becoming more nuanced. But the striking image Taylor was crafting shouldn’t undervalue the song’s masterful composition and hooky chorus. Only the most prejudiced of music snobs were now ignoring the strong songwriting skills she was starting to reveal.
7: No Body No Crime
Enlisting Haim for vocal support, “No Body No Crime” is a stylized slab of confident storytelling that generated some of the strongest critical reviews from the Evermore album. It’s a pop-rock murder-ballad that saw the female rock band enjoy their first hit single in their homeland after more success in markets such as the UK. The only disappointment for fans? There was no video for the song, which was issued as a single in the grip of the global COVID-19 pandemic.
6: We Are Never Ever Getting Back Together
Demonstrating not only the immediacy of the best Taylor Swift songs, but also how young artists can assert authority on their own destiny, “We Are Never Ever Getting Back Together” was the first taste of Taylor’s fourth album, Red. Creatively, the song pitched the confident message of romantic control ahead of the era when women’s exploitation across this, and so many areas of life, was being truly exposed – and, professionally, it became Taylor’s breakout work as her first collaboration with legendary hit-makers Max Martin and Shellback. This surely was the sound of a young woman taking control of her career by the scruff of its neck. Contagiously addictive, “We Are Never Ever Getting Back Together” became her first Billboard chart-topper and its lyrics provided plenty of fuel for the tabloids, who were becoming increasingly obsessed with this enigmatic new star.
5: Love Story
Coming from the period before she herself became ubiquitous, most international listeners would pick “Love Story” as the song that first made them aware of the rising star. Still in her teens when it was released, Taylor was cast as a romantic princess in the fondly remembered video – an interesting spin on the persona the frenzied tabloids would seize upon and distort in the years ahead. While still identifiably a country song, “Love Story”’s unashamedly pop production helped it become a huge radio hit, and the song was widely nominated in awards season. Commercially, it was Taylor’s first smash, making No.1 in Australia, No.2 in the UK and entering the Top 5 in the US.
4: I Knew You Were Trouble
On “I Knew You Were Trouble,” Taylor Swift proved she knew how to cause trouble herself, as the box she had just broken free from with “We Are Never…” clearly wasn’t one she would ever return to. Entering a period when almost every new song could lay claim to being among the best Taylor Swift songs, this insistent pop-country hybrid, built around a hooky rock riff, was another smash crossover, peaking at No.2 on both sides of the Atlantic. Another Max Martin and Shellback collaboration, “I Knew You Were Trouble” was premiered at the 40th American Music Awards in another classic live performance that showcased Taylor’s increasing stage confidence.
This breezy title track from 2019’s Lover is a stylized slice of 60s Americana and has been issued in different remixes that don’t quite improve on the original’s effortless air. Taylor admits “Lover” came quickly and there’s something about its waltz-like easy-come, easy-go charm that sets it above from what’s already a uniformly strong album (arguably her best and certainly her strongest pop record). “Lover” rightly made many of the lists documenting the best songs of the year.
Opening Evermore, “Willow” sets the tone for the parent album, and its understated groove gently draws you in and was picked to promote the project as the lead single. “Willow” is one of those songs that settles somewhere deep inside your psyche and also made an immediate impression on the radio programmers. Taylor’s gift for catchy melancholia had been indisputably recognized across the pairing of Folklore and Evermore in the strangest of recent years. The pandemic has thus far deprived audiences of seeing these songs in a live context, but the Taylor that returns to the touring circuit certainly won’t be one we have seen before.
Following the release of her stripped, back acoustic pandemic albums, Folklore and Evermore, Swift returned to her full pop prowess with the release of Midnights and its breakout single, “Anti-Hero.” With her trusted collaborator Jack Antonoff at her side, Anti-hero is the evolution of her past work: from the synth-pop sheen of 1989, to the self-effacing streak of reputation and the intricate lyricism of Folklore and Evermore. The results are a densely-packed, infectious earworm and self-aware anthem.