What are the best and worst Taylor Swift songs? Ever since Swift made the transition from country to pop, she’s reigned supreme, with hit single after hit single topping the charts. But Swift is more than just a pop singer; she’s a master at taking her own personal heartbreak and tragedy, and turning that pain into songs that are both relatable and catchy at the same time.
Swift launched her career when she was just a teenager, and has been dominating the charts since 2006. With seven studio albums and multiple Grammy wins, Swift is undoubtedly one of the biggest stars in the music industry, and will go down in history for all her accolades.
However, despite Swift’s many successes and serious songwriting talent, there are still some songs that aren’t exactly Swift’s best work, which contrast pretty intensely with her hits. So, if you want to take a walk down memory lane and relive all the best and worst Taylor Swift songs, then keep reading.
BEST: There's a reason Taylor Swift's "All Too Well" is a favorite among fans and critics
For Taylor Swift fans, or Swifties, as they’re known, there’s one song from Swift’s catalog that will always reign supreme. “All Too Well” is the emotional rollercoaster of a ballad from Swift’s album, RED, that paints a stunning and heartbreaking picture of a breakup. The song tells the gut-wrenching story in the way that only Swift can, and it has long been hailed as one of her best songs ever. Though the song only peaked at #17 on the Billboard Hot 100, it was still met with highly-regarded critical reception.
In fact, Rob Sheffield of Rolling Stone gave a very glowing review of the ballad (which he called her “most perfect” song), and even ranked it as the best song of the 2010s. “Every detail of ‘All Too Well’ is the calculating flourish of a master, from the plaid shirts to the crumpled-up paper to the walk home alone to the kitchen dance party to the way her fangs come out for that “yeeeeah” at the 4:37 point,” he wrote. That’s some seriously high praise!
WORST: Taylor Swift's "ME!" was seriously a flop
When Taylor Swift announced her seventh album, Lover – and here are all the secrets Taylor Swift revealed about her relationships on her album Lover – fans were ecstatic, according to NPR. Swift had just finished her Reputation stadium tour, and the pastel tones and dreamy fonts of Lover’s pre-release advertising were a stark contrast to the previous album’s darker, more dramatic tones. But the lead single from Lover, a duet between Swift and Brandon Urie called “ME!” was seriously lacking.
According to Billboard, “ME!” debuted at No. 20 on the charts, which is one of Swift’s lowest debuts for a lead single. And it didn’t exactly receive rave reviews, either. The Atlantic claimed that the song “is everything that gives pop a bad rap.” Additionally, Rolling Stone lists it as one of the worst Swift songs of all time. Sure, “ME!” is catchy, but with an lyrics like “Hey kids, spelling is fun?” the song is one of the star’s worst singles.
Putting the song aside, the music video for “Me!” is arguably pretty entertaining. To that end, here are the small details you missed in Taylor Swift’s “Me!” video.
BEST: Taylor Swift's "Cardigan" is a lyrical masterpiece
2020 wasn’t exactly the best of times, to say the least. But during the worst of times, Taylor Swift fans were treated to some pretty great news, when the singer announced she’d be releasing a new album, Folklore, in July of that year. The album was a departure from her catchy pop albums of the past, and there were some call-backs to her country days with tracks like “Betty.” However, one of the best songs on the album was “Cardigan,” which is also one of Swift’s best songs, period (via Vulture).
Not only is “Cardigan” a lyrical masterpiece, and one of Swift’s finest examples of storytelling, but the song is also super catchy. In fact, according to Billboard, “Cardigan” debuted at No. 1 on the Billboard Hot 100 chart. This accolade made Swift the first artist to hold the No. 1 spot on both the Billboard Hot 100 and the Billboard 200 charts in the same week. Clearly, Folklore – and here’s the real reason Taylor Swift named her album Folklore — was an impressive album, and “Cardigan” was genius.
For the curious, here’s what Taylor Swift’s “Cardigan” is really about.
WORST: Taylor Swift's "I Wish You Would" is a mess
In 2014, Taylor Swift released her groundbreaking album 1989, her first, fully-pop album that truly showed off her versatility as an artist. And while the album had more than a few hits and some real bops, there was one song from 1989 that just missed the mark — and was kind of a mess, to be honest. “I Wish You Would,” just wasn’t as impactful as other songs of Swift’s, thanks to its overly repetitive chorus.
According to Billboard, “I Wish You Would” peaked at No. 56 on the charts — not exactly the highest spot that Swift has achieved. But more than the song’s ranking, “I Wish You Would” also just didn’t represent Swift’s best abilities as a singer or songwriter. To that end, Vulture ranked it as the 105th worst Swift song, out of only 162.
Clearly, “I Wish You Would” fell flat. But despite the fact that it’s one of the least appealing songs in Swift’s catalog, it’s still undeniably catchy, as is seemingly everything she does.
BEST: Taylor Swift's "Ronan" is a tearjerker
Taylor Swift doesn’t stray away from first-person storytelling in her songs, as most lyrics can be traced back to her own romantic relationships. So when Swift ventures out and writes a song about someone or something other than herself, it can be a bit of a gamble. But with “Ronan,” the charity single Swift released in 2012, the emotions are so raw, it’s as though Swift herself had lived it (via AZ Central).
The song, inspired by a series of blog posts from mother Maya Thompson, tells the story of a little boy, Ronan — and his cancer diagnosis and death. Swift was moved by Ronan’s story and decided to tell it in song form, and the images she paints in the song are truly heartbreaking. No one deserves to die from cancer, but it’s especially gut-wrenching when a young child loses their battle.
With “Ronan,” Swift definitely stepped out of her comfort zone, but the result was equal parts gorgeous and emotional. The charts agreed, too. According to Billboard, “Ronan” debuted at No. 16 on the Billboard Hot 100; it’s still one of her best and most powerful songs to date.
WORST: Taylor Swift's "Innocent" is awkward to listen to
Listen, if you don’t know about the feud between Taylor Swift and Kanye West that started at the 2009 MTV VMAs, then you must be living under a rock. While the incident was years ago, it still haunts both Swift and West to this day. When West interrupted Swift’s acceptance speech for Video of the Year, jaws dropped all over as Swift was cut off on live television. Obviously, the feud between Swift and West has evolved so much since then that it’s easy to forget where it all began. But with Swift’s song, “Innocent,” the story was immortalized (via Billboard), though the song is kind of awkward to listen to.
In the song, Swift recalls her feelings of the 2009 incident, proclaiming that West is “still an innocent,” despite his gall. The song simplified all the complicated feelings Swift had about what happened, though it also seemed a little shallow. Though the point of “Innocent” was to paint Swift as the bigger, more forgiving person, it was just a little uncomfortable. Plus, according to Billboard, it only peaked at No. 12 when it was released.
BEST: Taylor Swift's "Blank Space" is pop perfection
With Taylor Swift’s album 1989, the singer-songwriter’s inner pop goddess came out and showed her true colors. The album was full of fun, catchy bops, and perhaps nothing on the album could beat “Blank Space.” While it wasn’t the lead single on the album, it ended up being among the most popular, with a music video to match.
In the song, Swift paints a very detailed and specific picture of her love life, and how it’s affected by her celebrity. She pokes fun at herself for being dubbed “insane,” and having “a long list of ex-lovers,” but the end result is pure pop magic. And, according to Billboard, Swift actually dethroned herself with “Blank Space” when it stole the No. 1 spot on the charts away from her previous single, “Shake It Off.”
Basically, “Blank Space” helped Taylor Swift to become the pop famous legend that she is today, and its smart lyrics and unshakable melody helped make it one of her absolute best songs ever.
WORST: Taylor Swift's "Better than Revenge" was kind of sexist
As is the case with most people, Taylor Swift wrote some not-so-great songs when she was younger. Specifically, in “Better Than Revenge,” Swift painted quite a sexist picture, and it really hasn’t aged well. The song, from Swift’s 2010 album Speak Now tells the story of a woman who stole Swift’s boyfriend, and how Swift is seeking revenge on her. It didn’t take long for people to realize that Swift was likely singing about Joe Jonas (via Entertainment Weekly), who she dated in 2008, and who unceremoniously dumped her in an infamous phone call for someone new, actress Camilla Belle.
And while “Better Than Revenge” did pretty well on the charts, peaking at No. 6, according to Billboard, it’s still not her best work. Swift has changed so much since she wrote that song, and it’s unlikely that she’d ever sex-shame or blame a woman after a breakup anymore. Still, “Better Than Revenge” proved that Swift wasn’t always as evolved and politically correct as she is now, and for that, it remains one of her worst songs.
BEST: Taylor Swift was so insightful in "Fifteen"
There are few things as dramatic and emotional as being a teenager. Honestly, just existing as a teenager in the world is rough. Between all the hormones, the stress from school, and the pressure to get into a good college and find a good career, it’s no wonder teenagers are constantly lashing out. But in Taylor Swift’s song, “Fifteen,” the blonde proves to be both insightful about and understanding of the teenage struggle, as noted by Vulture.
As Billboard reported, “Fifteen” peaked at No. 7 on the charts, which is pretty good for a non-lead single song on an album. That’s especially considering the album it was on, Fearless, which featured a lot of catchy, fast tunes with which “Fifteen” had to compete. But the song didn’t need to be especially catchy or fun to truly succeed, as it was relatable to just about everyone who was a teenager or had ever been one. With touching lyrics referencing Swift’s longtime best friend, Abigail, to hints at a friend getting hurt by a boy, “Fifteen” remains one of Swift’s best songs — and necessary listening for anyone in high school.
WORST: Taylor Swift's "Today Was A Fairytale" was too cheesy
In 2010, Taylor Swift made her big-screen debut in the star-studded rom-com Valentine’s Day, alongside the likes of Julia Roberts — who’s undergone a stunning transformation — and Bradley Cooper, as noted by MTV News. And while the film itself was charming if predictable, Swift’s single, “Today Was A Fairytale,” that she released for the film, was the same. The song is happy, simple, and admittedly pretty forgettable, which makes it one of Swift’s worst.
While Billboard didn’t exactly slam the song in a review, it does mention that “the lyrics are driven more by sweeping emotion than by the kind of specific, youth-focused imagery,” Swift usually uses, and it’s that departure that makes the song one of her worst. Though “Today Was a Fairytale” peaked at No. 1 on the Billboard Hot 100, it just doesn’t have the lasting power of so many other Swift songs.
Basically, “Today Was A Fairytale” is just too cheesy; Rob Sheffield ranked it the 81st worst Taylor Swift song for Rolling Stone, proving that it really is kind of a bore.
BEST: Taylor Swift's "New Year's Day" was subtly beautiful
According to Billboard, Taylor Swift’s album reputation was turning-point in the artist’s career. The lead single, “Look What You Made Me Do,” and its music video told fans that Swift was done letting other people write her narrative. But the last song on the album, “New Year’s Day,” told a different story. The song only peaked at No. 6 on the Billboard Hot 100 chart, but that doesn’t make it any less beautiful. In fact, it’s one of Swift’s best songs ever.
“New Year’s Day” stands apart from the rest of the album, but that’s why it’s one of her best songs. Rolling Stone even gave “New Year’s Day” a glowing review, calling it a “deep cut”, hailing Swift’s ability to blend the song perfectly with the rest of the album. The review also stated that “New Year’s Day” feels “warm and full,” and that’s exactly right. It’s like a nice hug at the end of a long day, and Swift totally nailed the feeling of starting over, making the song’s placement as last on the album even more perfect.
WORST: Taylor Swift's "All You Had To Do Was Stay" is too repetitive
Taylor Swift’s 1989 was full of fun, catchy tunes that truly showcased her pop abilities, according to Vulture. But one song on the album, “All You Had To Do Was Stay” was just an overly-repetitive mess that you probably hit “skip” on when listening to the album. The song only peaked at No. 25 on the Billboard Hot 100, and there’s a reason for that: it’s just not very fun, or worthwhile, to listen to.
Rob Sheffield ranked “All You Had To Do Was Stay” as Swift’s 80th worst song for Rolling Stone, which says a lot. It might not be the absolute worst, but it’s definitely far from the best. Truly, the tune is far too repetitive, and it’s not as poignant or meaningful as a lot of Swift’s other tracks.
1989 may be a great album, but “All You Had To Do Was Stay” is one of her worst songs.
BEST: "Wildest Dreams" showed a new side to Taylor Swift
It’s no secret that 1989 made Taylor Swift a household name. The album featured so many great songs, including “Wildest Dreams,” one of Swift’s first explorations into a new sound. In the song, Swift takes on a dreamy, raspy voice as she sings of forbidden love, broken hearts, and of course, her signature red lips. The song truly showed Swift’s versatility, and was worth listening to.
According to Billboard, “Wildest Dreams” peaked at No. 5 on the charts, an impressive feat for Swift, who had more than one chart-topper on 1989. And while The Guardian points out some similarities between “Wildest Dreams” and Lana Del Ray’s song style, the publication also notes that Swift’s song is smart; it casts the man as the victim, essentially flipping the script.
Despite controversy from the music video for the song (via Vulture), “Wildest Dreams” remains one of Swift’s best, and most adventurous, songs.
WORST: Taylor Swift's "The Other Side of the Door" is melodramatic
When Taylor Swift first emerged onto the music scene in 2006, she was a country music darling. She had a twang in her voice, cowboy boots on her feet, and a love for slamming doors, pouring rain, and pick-up trucks. And while her debut album, Taylor Swift, featured some great country songs, “The Other Side of the Door” wasn’t one of them.
“The Other Side of the Door” is almost a country-music cliche. While other Swift songs like “Tim McGraw,” or even “Betty” — here’s what the Taylor Swift song is really about, too — prove that Swift knows what she’s doing when it comes to country, this song remains one of her worst. “The Other Side of the Door” peaked at No. 11 on the Billboard charts, which obviously isn’t bad, but the lyrics and musicality of the song are both lacking.
Rob Sheffield ranked “The Other Side of the Door” as the 139th worst Swift song ever for Rolling Stone, and complained of its abundance of cliché in his reasoning. Truly, Swift has done so much better since “The Other Side of the Door” was released!
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