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Best Taylor Swift Songs: 20 Essential Tracks For Swifties

In a career that has ranged from country protégé to pop powerhouse within a decade, the best Taylor Swift songs show a true artist controlling her destiny.

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Photo courtesy of Big Machine

There are few artists today who receive such intense attention as Taylor Swift. With each new album, retailers rejoice in the expectation of a market-defining sales boom; devoted fans seize on every sentence in her songs, desperately trying to decipher a deeper message; and millions of others find comfort in the very best Taylor Swift songs: powerful pop hits certain to provide the soundtrack to the next few months. But few acts have been on such an impressive journey as Swift, born on 13 December 1989. Who would honestly have predicted her path from country protégé to pop powerhouse in a little over a decade?

Listen to the best Taylor Swift songs on Apple Music and Spotify, and scroll down for our 20 essential tracks for Swifties.

While still at high school, Taylor 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.

In many ways, its follow-up, ‘Teardrops On My Guitar’, represents Taylor’s true breakthrough, hitting the Billboard Top 20 and becoming a live favourite. 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.

Taylor’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, and earning its place among the best Taylor Swift songs when it became 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.

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.

Chosen as the third single from Taylor’s second LP, Fearless, ‘You Belong With Me’ was another anthemic, pop-flavoured 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 show.

Internet leaks plague many artists, and Taylor 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.

That single’s follow-up, ‘Back To December’, is one of the most tender ballads Taylor has ever recorded. Its yearning elegance sadly saw it sidelined 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.

Launching in 2011, The Hunger Games was a huge international film franchise based on a trio of best-selling novels. Artists were clamouring to get their work onto the soundtracks, but Taylor’s rocky contribution, and one of her two soundtrack contributions, ‘Safe And Sound’, recorded with alternative country act The Civil Wars, showed that Taylor was now finally starting to secure more favourable press.

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.

On ‘I Knew You Were Trouble’, Taylor 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.

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.

It’s a sad reality that so many strong female icons still end up getting characterised 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 centred 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.

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.

By now, Taylor 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 humour 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.

When a rumoured remix of the 1989 album track ‘Bad Blood’ turned out to be a collaboration with rapper Kendrick Lamar, many thought Taylor 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.

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.

OK, so Zayn Malik gets about a bit, but the pairing with Taylor for 2017’s Fifty Shades Darker soundtrack resulted in a thoroughly adult electro R&B ballad with more than a hint of the sexual tension that characterised the movie series the song was placed with. Zayn, of course, has worked with Sia, MIA and Chris Brown, among others, but ‘I Don’t Wanna Live Forever’ was his biggest collaboration to date and the pairing went Top 5 around the world. Taylor wrote the track with hip-hop artist Sam Dew and Jack Antonoff from Fun.

When Right Said Fred got the call that their 1991 smash ‘I’m Too Sexy’ had inspired part of Taylor’s 2017 comeback, ‘Look What You Made Me Do’, they must have thought they’d won the lottery. Indeed, they probably have. 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.

After the edgier ‘Look What You Made Me Do’, ‘Gorgeous’ emerged as a midtempo ballad that harks back to a sweeter, more accessible Taylor. Pop radio immediately embraced the Max Martin/Shellback collaboration and, taken together, both singles showed that Reputation would ably cover Taylor’s stylistic diversity with yet another collection destined to rank alongside the best Taylor Swift songs.

When, just 18 months later, she emerged with another new track, ‘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 characterise all the obvious peaks of Taylor’s hit back catalogue. But it’s the clever blend that brings it all to life. Lyrically, ‘ME!’ marked a return to familiar themes, but the styling is new and adds 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 is one of the show’s best openings to date.

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