Anti-Hero: The ultimate Taylor Swift playlist

In 2006, Taylor Swift stormed onto the music scene with her self-titled debut album, and tracks like “Our Song” are why everyone started to take notice of this fresh-faced, wildly talented young songwriter. The third single from "Taylor Swift," it was her first No. 1 single on the Billboard Hot Country Songs chart and was later certified quadruple platinum by the Recording Industry Association of America. 

It’s pretty crazy to think that Swift first wrote “Tim McGraw” in about 20 minutes when she was a teenager because it’s definitely a song that’s wise beyond its years. Her debut single, “Tim McGraw” was certified Platinum and put Swift on the radars of country fans everywhere. 

In 2007, Swift stirred a minor controversy with the release of “Teardrops on My Guitar,” with some critics accusing the song of being “too pop” for a country hit. None of that mattered to fans, though, who heard their own experiences in Swift’s story about being smitten with someone who isn’t reciprocating your feelings.  

Her modern retelling of Romeo and Juliet, 2008’s “Love Story” also weaves in a little personal backstory in true Swift fashion. Since its release, the song has sold more than 15 million copies across the globe and is considered one of the most successful hit singles in recorded music history. 

Despite being a top-10 hit, it was an incident at the 2009 MTV Video Music Awards that made “You Belong With Me” go down in history. As Swift accepted the award for Best Female Video, rapper Kanye West interrupted her with his famous “I’m gonna let you finish” speech in support of Beyonce. The incident would inspire a rift between the two artists that continues to this day. 

After someone leaked “Mine” onto the internet in 2010, Swift was forced to release the lead single from her album "Speak Now" earlier than expected. This typical Swift love song with lyrics that reflected her growing maturity as a songwriter really resonated with fans, pushing the song to debut at No. 3 on the all-genre Billboard Hot 100 chart. 

The title track of Swift’s third album, “Speak Now,” is pure Taylor Swift at her best. With its simple (and catchy) acoustic melody and lyrics focused on trying to win back an ex-love by “speaking up” at his wedding, it’s one of Swift’s most iconic narrative tunes. 

Appearing on 2011’s Speak Now, “Mean” is a beloved anti-bullying anthem with a backstory that’s pretty personal for Taylor Swift. In an interview following the song’s release, she revealed that it was written about a music critic’s less-than-positive response to her performance at the previous year’s Grammy Awards. 

The anthem that anyone who’s tried to make the impossible work with an old flame, 2012’s “We Are Never Getting Back Together” is Swift at her sassiest and most defiant. Allegedly written about her ex-boyfriend and actor Jake Gyllenhaal, Swift’s never actually divulged the name of the person that she’s never, ever, ever getting back together with — like, ever! 

Swift’s transformation into a pop star was complete with the release of 2012’s Red, and “I Knew You Were Trouble” is one of the album’s most iconic tracks. Fans speculate that it was written about John Mayer, one of Swift’s famous exes, though she’s never confirmed who exactly the subject of this song about toxic relationships is really about it. 

Swift has tackled the “haters” plenty of times but perhaps never more directly than with “Shake It Off,” a fiery smash hit released in 2014 that clapped back at those who criticized her romantic relationships and musical choices. It also arguably marked the beginning of Swift’s transition from a country ingenue into a full-fledged pop icon. 

Taylor Swift’s love life has been both tabloid and lyric fodder since the beginning of her career, and she addresses how the media has covered her relationships with her boyfriends on 2014’s “Blank Space.” The tongue-in-cheek tune earned almost universal appeal from critics and fans alike and has since moved more than 11 million units. 

Arguably one of Swift’s most cryptic tunes, speculation over who “Bad Blood” is about still abounds. Some say that it’s about Katy Perry, the pop singer who Swift famously “made up” with in 2019, but Swift’s never confirmed that she’s the female musician who betrayed her, as the lyrics portray. 

Released on Swift’s critically acclaimed 2014 album, "1989," “Wildest Dreams” is Swift at her dreamiest and poppiest. The song’s lyrics and melody are great, but the video for the song is truly iconic. It was filmed on the African Serengeti and features Swift looking a whole lot like a modern Elizabeth Taylor. 

Collaborating with Jack Antonoff to produce the song’s bass-laden, electro-pop melody, “Look What You Made Me Do” is Swift at her most venomous. It could be a clap back at Kanye West, or maybe the media or perhaps Katy Perry. Whomever its target, there’s no denying that “Look What You Made Me Do” was one of 2017’s best songs. 

Swift began experimenting with electronic sonic elements before the release of 2017’s “Gorgeous,” but after its debut, it became one of her most distinctive tracks. It’s since been certified gold by the RIAA after selling more than half a million units.  

With cameos from fellow pop star Ed Sheeran and rapper Future, 2017’s “End Game” is indicative of Swift’s genre-melding sound of the past few years. Blending electro-pop, hip-hop and R&B elements, it’s a song that’s beloved by serious Swifties everywhere. 

Swift’s voice is given an electronic vibe with the assistance of a vocoder on 2018’s “Delicate,” a vulnerable track with a whole lot of depth. It’s Swift confronting the narrative that’s been shaped by the media, by fans and by the industry, contemplating what exactly that means for her personal life, making “Delicate” an intimate window of sorts into the mind of one of music’s favorite hopeless romantics. 

In what may be her most political song to date, Swift voiced her support for the LGBT community in a major way in 2019 with “You Need to Calm Down.” After the song’s release, she urged fans to sign a petition in support of passing the Equality Act, a bill that would ban discrimination on the basis of gender identity, sex, medical condition or sexual orientation. 

The title track of Swift’s much-anticipated 2019 album, “Lover,” was an instant hit. Co-produced by Swift and frequent collaborator Jack Antonoff, the song has since scored a Shawn Mendes remix and earned acclaim from the critics for its expressive lyrics, Swift’s ethereal vocals and its stripped-down sonic vibe. 

When "Cardigan" hit the charts in July, it debuted at #1 on the Billboard Hot 100, notching Swift her sixth number one hit. It also earned praise from critics, who found a lot to love in the song's laid-back sonic vibe and intricately crafted lyrics. 

Appearing on Swift's surprise 2020 album Folklore, "Mirrorball" is a stunningly beautiful song. Using a disco ball as a metaphor, Swift explores themes of fragility, reflecting light, and ultimately, what it means to be a star on this ethereal track. 

With "Anti-Hero," Taylor Swift coined the most popular phrase of 2022: "It's me, hi, I'm the problem, it's me." The song dives deep into Swift's own neuroses — and how she participates in them — which is a relatable theme for pretty much anyone. It was widely considered one of the best songs of the year, and scored Swift her longest-running #1 hit to date. 

Co-written and co-produced by Swift and Jack Antonoff, "You're On Your Own" earned praise from critics for its deeply thoughtful lyrics centered around her own life and experiences. It also was a huge hit among fans, topping out at #7 on Billboard's Global 200 chart.