Swift's debut album dropped in 2006, cementing her as a country darling. However, it wouldn't be long before the singer-songwriter became restless. Swift would soon transition into pop music, with 1989 being her first official pop album. While few have successfully transitioned from country to pop, Swift made it look like a breeze. She became the only artist in history to win the Grammy for Best Country Album and Best Pop Vocal Album.

Throughout the years, she's jumped around a lot, proving there's no mold she can't break. Swift has done it all, from R&B and trap influences on reputation to the folktales and acoustic productions of folklore. Swift also has twelve #1 Billboard Hot 100 hits with over 260 songs charting. In 2024, she became the artist with the most Grammy Album of The Year wins, breaking a record set by Frank Sinatra, Stevie Wonder, and Paul Simon. While many of Taylor Swift's songs resonated with her massive fanbase, a handful of them have become the tracks that define her career.

10 Our Song

Taylor Swift (2006)

In 2007, Taylor Swift released the third single off her debut album. "Our Song" was a track she wrote for her 9th-grade talent show. Swift pushed for the tune to make her debut album because her classmates told her they really liked it. While her record label didn't necessarily think listening to a bunch of teenagers' opinions was the smartest business move, Swift won her case. She then went on to build an entire career off of the opinions of teenagers and young women — two groups who aren't taken seriously enough.

"Our Song" was Swift's first single to go #1 on Billboard's Hot Country Songs and made her the youngest artist to ever single-handedly write and perform a #1 song on the Country charts. While it was still so early in her career, it foreshadowed just how powerful she would become and how capable she was of spitting out catchy songs.

9 Blank Space

1989 (2014)

Taylor Swift didn't just go pop when she released 1989; she took over the pop industry. Swift dominated the airways, and after "Shake It Off" debuted at #1 on Billboard's Hot 100, it remained there for four nonconsecutive weeks. When it was bumped from #1 a final time, it was "Blank Space" that knocked it from its throne, making Swift the first female to ever replace herself at #1. "Blank Space" received three Grammy nominations and is currently #320 on Rolling Stone's 500 Greatest Songs of All Time list.

Swift also made one thing clear with "Blank Space;" she always has the last word. Swift wrote from the perspective of the character the media created: A boy-crazy villain who uses men for song inspiration and acts irrationally when they leave her. The years of jokes about Swift's dating life and her habit of writing breakup songs would hold no power over her anymore.

8 Teardrops On My Guitar

Taylor Swift (2006)

By the time Taylor Swift released "Teardrops on My Guitar," she'd established herself as an artist on the rise in country music. However, the second single off her debut album was the first one she released to pop radio. For a lot of music fans who weren't up to date with the latest country stars, "Teardrops on My Guitar" would be the first song they ever heard from Swift.

Now she wasn't just on country music's radar, but the entire music industry. While she wouldn't release an official pop album for another seven years, "Teardrops on My Guitar" signaled that Swift had ambitions of crossing over genres. It was also the first time Swift released a pop remix of one of her songs specifically for pop radio.

7 Love Story

Fearless (2008)

With 264 songs charting on the Billboard Hot 100, "Love Story" remains one of Swift's best known. It's the only one of her songs she's performed at every single one of her tours and was one of the most nostalgic numbers at the Eras Tour. It was also the first single off her sophomore album, Fearless, which would go on to win Swift's first Grammy for Album of The Year.

Her incorporation of Shakespeare's famous lover characters, Romeo and Juliet, put Swift on the map. Swift also has an impressive story about writing the song in about 25 minutes on her bedroom floor after fighting with her parents over a guy she was dating. At this point, while Swift was still considered a country music artist, it was clear she was simultaneously an up-and-coming pop princess.

6 We Are Never Ever Getting Back Together

Red (2012)

In 2012, Taylor Swift finally found one of her songs atop the Billboard Hot 100 as "We Are Never Ever Getting Back Together" became her first #1 song. This time, she wasn't hiding her desire to be a pop star behind banjos or acoustic guitars. Red may still be categorized as a country album, but "We Are Never Ever Getting Back Together" signified that Swift was ready to make the jump to pop music.

While she would simultaneously release country singles throughout the Red era, the bubblegum pop single put her on the same playing field as the decade's biggest pop stars like Katy Perry and Lady Gaga. There was no going back to her curly hair and cowgirl boots days after Swift released "We Are Never Ever Getting Back Together."

5 White Horse

Fearless (2008)

While Swift was dominating the pop world with "Love Story," she was still making waves in the country genre, especially with her single "White Horse." Her album, Fearless, is still one of the highest-selling country albums of all time and has contributed to a shift in the genre. "White Horse" was the second single off Fearless, released exclusively to country radio and suggested she was not done with the genre just yet.

The song was Fearless' only heartbreak ballad released as a single and incorporated acoustic guitars, piano, and the cello. Most excitingly, "White Horse" won Best Country Song and Best Female Country Vocal Performance at the Grammys. When Swift approached the stage at the Grammys pre-show to accept her award, she exclaimed, "This is my first Grammy, you guys." While it may not be one of her best-known songs, it is the one that opened the door for her in The Recording Academy and showcased her songwriting and production skills.

4 Cardigan

folklore (2020)

When Taylor Swift canceled Lover Fest due to the COVID-19 pandemic, ticket carriers were devastated. However, little did they know Swift was in quarantine writing a new album and once again switching genres. At this point, Swift was a bonafide pop queen, and it seemed like she was in the genre for good. Unfortunately, the singer-songwriter received some criticism that her songwriting wasn't as strong as it had been earlier in her career. The public missed the days of her and her acoustic guitar dominating her albums, especially after their disdain for her Lover lead single "ME!"

While the world was going through one of the most unforeseen circumstances in history, Swift wasn't in the mood to make upbeat pop music. Instead, she took refuge in her cabin in the woods and her mystical imagination. folklore and signified her return to her singer-songwriter roots.

The song, along with others off folklore, went viral on TikTok, reintroducing fans to her music and prompting many to go back and listen to her older stuff again. It was certainly the song that jumpstarted her industry takeover, got fans excited about her rerecorded music, and inspired Swift to launch the Eras Tour. Swift's work on "Cardigan" and folklore put an end to cynics questioning her songwriting abilities, concluding that, yes, she really is that good.

3 Anti-Hero

Midnights (2022)

After cementing herself as the best singer-songwriter of her generation with folklore and evermore, Taylor Swift left her cottage-core aesthetic behind and reclaimed her pop star title with Midnights. "Anti-Hero" was the first single off the album. After years of having her breakup songs met with the criticism, "Maybe she's the problem," Swift finally itted it in the lyrics and reclaimed the narrative again.

The single became Swift's longest song at #1 on Billboard's Hot 100, spending eight weeks atop the charts. When "Anti-Hero" debuted at #1, nine other songs from Midnights landed beneath it, making her the first artist in history to dominate the top 10. "Anti-Hero" proved Swift could be a mastermind songwriter and a pop genius simultaneously.

2 Cruel Summer

Lover (2019)

"Cruel Summer" always felt like it should have been the song of the summer. Unfortunately, Lover was released at the end of the summer of 2019. When the summer of 2020 came around, the world was in the throes of the COVID-19 pandemic, and Swift had canceled her Lover tour. Luckily, during the Eras Tour, "Cruel Summer" had its moment to shine as the first full song Swift sang.

It became the defining song of the record-breaking tour, propelling it to the #1 spot on Billboard's Hot 100 in October 2023. It was an unusual accomplishment as songs don't typically reach number one years after release — Mariah Carey's "All I Want For Christmas Is You" is the exception. However, "Cruel Summer" hit #1 four years after its release and remains a beloved collaboration between Swift and Jack Antonoff.

1 All Too Well (10 Minute Version)

Red (Taylor's Version) (2021)

No song defines Taylor Swift's career quite like "All Too Well (10 Minute Version.)" The original song was released in 2012 as Swift's track 5 song on Red. While it was never released as a single, it became a fan favorite, prompting Swift to perform it at the 2014 Grammy Awards. It has always been one of Swift's most heartbreaking ballads and one of her lyrical best. Some have even referred to it as her magnum opus. Soon after its release, Swift let it slip that when she was originally penning the song, it was about 10 minutes long.

Thus, the 10-minute version lore began and became something fans hounded her about for a decade until the 10-minute version wasn't just a folktale anymore. In 2021, when Taylor Swift released Red (Taylor's Version), she included the ten-minute version of the song as a vault track. "All Too Well (10 Minute Version)" debuted at #1 on the Billboard Hot 100 charts, becoming the longest song in history to go #1.

However, what makes the song the most defining of her career is not because of its in-depth storytelling, impressive lyrics, or commercial success. It's because of the connection it has had with her audience, and Swift has built her entire career on her connection with her fans. After all, it was Taylor Swift's fans who pushed her to release "All Too Well (10 Minute Version)" to begin with.