'Love Story,' which Taylor wrote in just twenty minutes while sitting on her bedroom floor, became one of her biggest hits and is now one of her most memorable songs.

In this high school retelling of Romeo and Juliet, Shakespeare meets country music. While the star-crossed fairy-tale relationship that prompted Taylor to create the song never came to fruition, the same relationship led Taylor to write 'White Horse' from the same album.

Most foreign listeners would choose "Love Story," which was released before she became famous, as the song that initially made them aware of the budding star. Taylor was still in her teens when the video was aired, and she was presented as a romantic princess in it — an unusual twist on the identity that the frenzied tabloids would grasp and alter in the years to come. While "Love Story" is still recognizable as a country song, its unabashedly pop production helped it become a massive radio smash, and the song was extensively nominated during awards season. It was Taylor's first commercial hit, reaching No. 1 in Australia, No. 2 in the United Kingdom, and No. 5 in the United States.

Album: “Fearless”

Songwriter: Taylor Swift

Accolades: “Love Story” took Best Music Video at the CMT Music Awards and the Country Music Association Awards.

Taylor Swift had mastered the event footage by the time 1989 was released. "Blank Space" will be remembered for its iconic high-camp advertising video, but the song stands on its own, easily earning a spot among Taylor Smith's best tracks. The electro-pop track's arch, knowing lyrics given with a splash of good humor propelled it to the top of the Billboard charts and earned Taylor three Grammy nominations, as well as wins at the MTV Music Awards and the American Music Awards.

Album: “1989”

Songwriters: Taylor Swift, Max Martin, Shellback

Accolades: Right after “Shake It Off,” Swift earned another no. 1 here, becoming the first woman in history to succeed herself at the top of the charts, and scored Grammy bids for Record of the Year, Song of the Year and Best Pop Solo Performance for the song.

"Shake It Off" was a song that made a literal and lyrical statement at the same time. Taylor's "Shake It Off," which broke her totally free from her country roots, was an out-and-out pop revolution. It was the lead single off her 1989 album (called after the year she was born), and it was a risky but yet mainstream move that would go down in history as one of Taylor Swift's best songs. Taylor's captivating reinvention was rewarded with her biggest hit to date and a chart-topping position in her hometown, thanks to the song's nostalgic atmosphere. "Shake It Off" reiterated the mantra that the boldest artists always stay true to themselves while preserving her aptitude for generating melodies that appealed to a wide variety of fans.

This Toni Basil-esque cheerleader yell was interspersed among the album's 80s synth-pop sophistication. If Red had raised Taylor's profile in the public eye, 'Shake It Off' was the moment when she became so famous that she could be seen from space.

The phrase "this sick beat" was trademarked to Swift by the US Patent and Trademark Office because the song became such a pop culture sensation.

Album: “1989”

Songwriters: Taylor Swift, Max Martin, Shellback

Accolades: The song instantly went to number-one on the Billboard Hot 100 and earned Grammy nominations for Record of the Year, Song of the Year and Best Pop Solo Performance.

"You Belong With Me," the third single from Taylor Swift's second album, Fearless, was another anthemic, pop-flavored country track that became her biggest hit in the United States when it reached No. 2. Taylor's styling – this time as the high-school sweetheart that other young ladies might still identify to – was getting more subtle as she grew more confident in her video performances. However, the song's brilliant composition and catchy chorus should not be overlooked because of the vivid image Taylor was attempting to create. Only the most jaded of music snobs could ignore the great songwriting abilities she was beginning to display.

Not only is "You Belong With Me" nostalgic, but it's also one of her most popular songs. The music video was nominated for a VMA award in 2009, and rightfully so. It takes a fresh approach to the typical "nerdy girl meets football star" theme, and it hooks listeners with a catchy chorus and intriguing verses.

Favorite Lyric: Walk in the streets with you in your worn-out jeans/I can’t help thinking this is how it ought to be/Laughing on a park bench thinking to myself/Hey isn’t this easy?

Album: “Fearless”

Songwriters: Taylor Swift, Liz Rose

Accolades: Swift broke through at the Grammys when this song was nominated for Record of the Year and Song of the Year, the same ceremony where “Fearless” won Album of the Year.

Taylor drew inspiration from her failed romance with Harry Styles even before 1989.

Styles acknowledged that it wasn't "impossible to access that feeling when the person the song is directed at is standing side of the stage watching" during a fiery performance of the song at the 2013 Brit Awards, where she was in the audience.

Taylor Swift proved she knew how to stir problems on "I Knew You Were Trouble," proving that the box she had just broken free from with "We Are Never..." wasn't one she would ever return to. This relentless pop-country hybrid, constructed around a hooky rock riff, was another big crossover, landing at No. 2 on both sides of the Atlantic as part of an era when practically every new song could claim to be among the best Taylor Swift songs. "I Knew You Were Trouble," another Max Martin and Shellback composition, was debuted at the 40th American Music Awards in another memorable live performance that displayed Taylor's growing stage confidence.

Album: “Red”

Songwriters: Taylor Swift, Max Martin, Shellback

Accolades: The music video won Best Female Video at the VMAs.

This heart-wrenching break-up ballad finally came to Taylor after a six-month writing block that followed a particularly traumatic end to a relationship. It's a fan favorite and the song from Red that Taylor has always characterized as the toughest to write.

The song, written again with Liz Rose, is widely considered to be about Jake Gyllenhaal, whom Taylor briefly dated in 2010; a hypothesis that Swifties leap on at every opportunity.

"All Too Well" is the song that can be played repeatedly without becoming monotonous. It's another painful story about two lovers who are no longer together and reminiscing about what they used to have. Her narrative skills are on full display in this song, and her heartfelt melodies and words never fail to bring tears to my eyes. Her voice has a strong but gentle tone to it. Because of the quality that it gives in every syllable, this song will go down in music history for all time.

Album: “Red (Taylor’s Version)”

Songwriters: Taylor Swift, Liz Rose

Accolades: This expansion of the song she originally recorded in 2012 debuted at number-one on the Billboard Hot 100, making it Swift’s eighth chart-topper and the longest number-one song in Billboard history.

Taylor Swift's song "Back To December" is one of her most emotional songs. Its wistful elegance pushed it to the bottom of many international charts, but Taylor's American fans embraced it, propelling it to No. 6 on the Billboard Hot 100 and a respectable showing on the Adult Contemporary chart. It's hard to think that this honest, knowing lyric was written by a woman who was only in her early twenties at the time.

'Back to December,' with soft guitar and string flourishes against a winter soundtrack, isn't quite as Christmassy as the title suggests, but it's perfect for the bereaved (and the heartbreakers). Swift, in a similar vein to 'champagne troubles,' lifts her hands up, eats her pride, and sings honestly of her regret towards a past partner.

The country-pop song has a softness to it that makes the singer's guilt ache even more. The bridge of the song is where the song reaches its height, as she tries to restore exposed memories and correct where she went wrong. She realizes it's too late, and that simply loving someone isn't enough: ‘I'd go back in time and change it, but I can't’. Taylor isn't afraid to be vulnerable and share her insecurities; she apologizes and expects nothing in return.

Album: “Speak Now”

Songwriter: Taylor Swift

Accolades: The single won Swift the Teen Choice Award for Choice Break-Up Song.

"Willow," the first single from Evermore, sets the tone for the parent album with its unobtrusive groove that softly draws you in. It was chosen as the project's debut single to promote the project. "Willow" is one of those tunes that sinks deep into your subconscious and makes an immediate impression on radio programmers. In the oddest of recent years, Taylor's ability for captivating melancholy had been undeniably recognized throughout the coupling of Folklore and Evermore. The pandemic has prevented listeners from seeing these songs performed live so far, but the Taylor who returns to the road will undoubtedly be unlike any other.

Album: “Evermore”

Songwriters: Taylor Swift, Aaron Dessner

Accolades: It debuted at number-one on the Billboard Hot 100 singles chart.

This breezy title tune from 2019's Lover is a stylized slice of 60s Americana that has been released in a variety of remixes that fall short of the original's casual air. Taylor confesses that "Lover" came swiftly, and there's something about its waltz-like easy-come, easy-go charm that elevates it above the rest of the album (arguably her best and certainly her strongest pop record). "Lover" was rightfully included on several of the year's finest song lists.

Album: “Lover”

Songwriter: Taylor Swift

Accolades: “Lover” was nominated for a Grammy for Song of the Year and the Art Directors Guild Award for excellence in production design.

"We Are Never Ever Getting Back Together" was the first taste of Taylor Swift's fourth album, Red, and it demonstrated not only the immediacy of the best Taylor Swift songs, but also how young artists can establish authority over their own future. The song was Taylor's breakout work as her first collaboration with legendary hit-makers Max Martin and Shellback, and it pitched the confident message of romantic control ahead of the era when women's exploitation across this, and so many other areas of life, was truly exposed – and it was Taylor's breakout work as her first collaboration with legendary hit-makers Max Martin and Shellback.

"We Are Never Ever Getting Back Together," which was infectiously addicting, became her first Billboard chart-topper, and her lyrics provided plenty of fodder for the tabloids, who were becoming increasingly enthralled with this enigmatic new star.

Album: “Red”

Songwriters: Taylor Swift, Max Martin, Shellback

Accolades: The song became Swift’s first to hit no. 1 on the Billboard Hot 100 and she earned numerous awards and nominations including Record of the Year at the Grammys.

Taylor Swift has achieved the zenith of her musical career with "You Need To Calm Down." She was aiming the limelight (that had threatened to blind her) back at us all instead, cleverly referencing her tabloid narrative in the video – which was named clip of the year at the MTV Video Music Awards. Of course, there's more to this hook-heavy masterpiece than meets the eye.

Taylor has frequently utilized her platform to address a wide range of subjects, and this song relates to the 21st Century's increasingly divided culture. Great musicians entertain with a message, and Taylor has a lot to say on Lover, the album's undeniable high point, for which she was nominated for a Grammy for Best Pop Solo Performance.

Album: “Lover”

Songwriters: Taylor Swift, Joel Little

Accolades: The vibrant music video won the MTV VMA for Video of the Year while the song was nominated for a Grammy.

Taylor Swift penned "Tim McGraw" while still in high school, a beautiful ballad that reflects her belief that music can cure most of life's afflictions. It's a theme Taylor would return to many times in the years to come, with the veteran country star's music giving her with the support she needed during an early romantic crisis while also inspiring the song. It was this song that drew the attention of the Big Machine label, which signed the 14-year-old when she was just 14.

"Tim McGraw," co-written with long-time early collaborator Liz Rose, proved the label's faith when it charted in the US country charts in the summer of 2006, and even crossed over to the US Billboard Hot 100, reaching at No.40 in an early indication of what the best Taylor Swift songs could achieve.

Favorite Lyric: When you think happiness/I hope you think “that little black dress”/Think of my head on your chest/And my old faded blue jeans

Album: “Taylor Swift”

Songwriters: Taylor Swift, Liz Rose

Accolades: Swift’s debut single earned her a CMT Music Award for Breakthrough Video of the Year.

Taylor Swift's true breakthrough came with this song, which reached the Billboard Top 20 and made her a live favorite. "Teardrops On My Guitarstill-only-midtempo"'s beat delivered her first epic chorus and became a solid staple in the star's early live appearances; the picture of Taylor dazzling on stage in a shimmering dress and omnipresent cowboy boots is eternally connected with the music.

It became Taylor's first UK hit (though it failed to crack the Top 40) and the best-performing single from her self-titled first album after being repackaged for worldwide release.

Album: “Taylor Swift”

Songwriters: Taylor Swift, Liz Rose

Accolades: Kicked off the MTV Video Music Awards’ love affair with Swift, earning a nomination for Best New Artist in 2008.

Following 1989's original high-octane power-pop, "Wildest Dreams," released in August 2015, was a welcome departure into calmer seas. Taylor was at her most seductive in the ethereal dream-pop ballad, which was featured in an Out Of Africa-inspired video co-starring Scott Eastwood. It became her first song to top the Billboard dance radio charts in remixed form, illustrating that the best Taylor Smith tracks can easily carry her into new terrain.

Album: “1989”

Songwriters: Taylor Swift, Max Martin, Shellback

Accolades: It was a top-10 hit on the Billboard Hot 100 singles chart.

Right Said Fred must have believed they'd won the lotto when they learned that their 1991 hit "I'm Too Sexy" had inspired a portion of Taylor Swift's 2017 comeback single "Look What You Made Me Do." Yes, they most likely did! The song broke records all around the world and gave Taylor and co-writer Jack Antonoff, who also produced it, their first UK chart-topper. "The old Taylor is no longer alive," she declared to the globe. It appeared that the new one would suffice.

Album: “Reputation”

Songwriters: Taylor Swift, Jack Antonoff, Fred Fairbrass, Richard Fairbrass, Rob Manzoli

Accolades: It broke the record for most streams in one day on Spotify and became Swift’s fifth no. 1 single on the Billboard Hot 100.