We Did the Impossible and Ranked Taylor Swift’s 50 Best Songs of All Time
In this year of our lord 2024, as we await the release of Taylor Swift's eleventh studio album, The Tortured Poets Department (dropping April 19, in case you were somehow unaware), it's pretty clear that Swift is one of the most prolific songwriters in the game. Not only is she constantly creating new music (she started working on TTPD right after finishing Midnights), she's consistently putting out absolute bangers and lyrical masterpieces. So, while we await her next release, my fellow Cosmo editors and I did the impossible and crafted a definitive ranking of the 50 best Taylor Swift songs—so far.
Quick disclaimer before we dive in: This was...an incredibly hard task. Swift's catalog is vast—10 albums, vault songs, Taylor's Versions, etc—and different albums speak to different fans. And in the spirit of celebrating all of Taylor's eras, this list includes every album from Taylor Swift to Midnights. Once the Cosmopolitan-editor-curated list of best Taylor Swift songs was officially determined by the Swifties in our office, I ranked the songs by preference and impact (hey, someone's gotta do it!). My ranking might not be the exact same as yours, and we may disagree on the details, but let's be real: if you're a Swiftie who doesn't have "All Too Well (10-Minute Version)" in your top 5 best Taylor Swift songs, are you even really a fan? Let's get into it...
"Tim McGraw"
Let's kick things off with Taylor's debut album, shall we? Former Cosmopolitan Senior Editor of News Analysis and Opinion Naureen Khan says this is the song that made her realize just how big Swift could be back in 2006. "We should've known she was a genius. The lyricism! The pining! The images!!"
Best lyric: "When you think Tim McGraw / I hope you think my favorite song / The one we danced to all night long / The moon like a spotlight on the lake."
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"Dancing With Our Hands Tied"
No matter where you stand on the Reputation album, it's undeniable that it includes some of Swift's most-experimental work. With its house music vibes, "Dancing With Our Hands Tied" doesn't sound like any other Swift song, hence its spot on the list.
Best lyric: "I loved you in spite of / Deep fears that the world would divide us / So, baby, can we dance? / Oh, through an avalanche?"
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"Mary's Song (Oh My My My)"
This deep cut from Swift's debut album is a personal fave of Cosmopolitan Beauty Editor Beth Gillette, who calls the masterpiece "one of the first songs I heard of Taylor's where she masterfully tells a love story from start to finish."
Best lyric: "I'll be 87, you'll be 89 / I'll still look at you like the stars that shine / In the sky, oh my my my"
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"I'm Only Me When I'm With You"
Swift's love songs may have played a major role in making her a billionaire, but her songs about friendship, like "I'm Only Me When I'm With You," deserve some credit, too. The early Swift music video features some cute BTS footage of her with her friends and family, further adding to the wholesomeness of the lyrics and message.
Best lyric: "And I don't try to hide my tears / My secrets or my deepest fears / Through it all nobody gets me like you do"
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"This Is Why We Can't Have Nice Things"
If I had to pick one song to describe Swift's Reputation Era, it would be "This Is Why We Can't Have Nice Things." Lyrically, it's the most explicit song about what she experienced during the whole Kanye West/Kim Kardashian feud. It's also pretty damn catchy.
Best lyric: "It was so nice being friends again / There I was, giving you a second chance / But you stabbed in in the back while shaking my hand"
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"Cowboy Like Me"
Cosmo's Assistant News Editor Samantha Olson is convinced that Evermore's "Cowboy Like Me" features "some of the best lyrics of Swift's career," and is also one of her best songs. As a fellow Swiftie, I have no choice but to respect her assessment—she's not wrong. I mean, pls see the below...
Best lyric: "Now you hang from my lips / Like the Gardens of Babylon / With your boots beneath my bed / Forever is the sweetest con"
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"Gold Rush"
Romantic relationships are hard, but sometimes, having a crush can be just as exhausting. As described in "Gold Rush," the constant wondering of what the other person is thinking or wanting is a special kind of hell. "I love how this song contrasts happy feelings with the anxiety of falling for someone," says Cosmopolitan's Senior Astrology Editor Erika W. Smith.
Best lyric: "I don't like that falling feels like flying 'til the bone crush"
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"No Body, No Crime" feat. HAIM
Another iconic Swift revenge track, "No Body, No Crime," is, in my mind, one of her best in the storytelling genre. There is just something so satisfying about women coming together to avenge their friend by taking out her cheating/murdering husband. Girl power!
Best lyric: "Good thing my daddy made me get a boating license when I was fifteen / And I've cleaned enough houses to know how to cover up a scene"
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"You're Losing Me"
Released as a vault song off Midnights, Swifties believe "You're Losing Me" is about the singer's former relationship with Joe Alwyn, and they make a compelling case. But the song isn't good because of what it reveals about Swift's personal life; it goes way beyond that, both lyrically and symbolically. Featuring the sound of Swift's heartbeat (much like 1989's "Wildest Dreams"), the track's mix of depression and heartbreak leads into a standout bridge (in classic Swift fashion), ranking it up there with some of her best vulnerable work.
Best lyric: "And all I did was bleed as I tried to be the bravest soldier / Fighting in only your army / Frontlines, don't you ignore me / I'm the best thing at this party (You're losin' me) / And I wouldn't marry me either / A pathological people pleaser / Who only wanted you to see her."
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"Should've Said No"
Just as the sun will always rise in the East, Swift will always write a good breakup song—which was proven all the way back on her debut namesake album. "Should've Said No" is the O.G. of Swift's genre of petty revenge tracks that absolutely slap.
Best lyric: "You shouldn't be beggin' for forgiveness at my feet / You should've said, 'No' / Baby, and you might still have me"
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"New Romantics (Taylor's Verson)"
Listen, 1989 undeniably includes some of Taylor's biggest hits—from "Blank Space" to "Shake It Off" and "Wildest Dreams," which is why this bonus track often gets lost in the shuffle. But it shouldn't, according to Cosmopolitan Senior Editor Lauren Alexis Fisher. "New Romantics is such an underrated bop and absolutely should've earned a spot on the album, not just as a bonus song," she says. "To me, it romanticizes being young and riding the waves of dating, love, and heartbreak with your friends."
Best lyrics: “Heartbreak is the national anthem / We sing it proudly / We’re too busy dancing / To get knocked off our feet / Baby, we're the new romantics / The best people in life are free.”
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"I Knew You Were Trouble (Taylor's Version)"
A quintessential Swift breakup song from the Red era. It's truly impossible to listen to this song and not want to belt out the chorus. Her power!
Best lyric: "And the saddest fear comes creepin' in / That you never loved me, or her or anyone, or anything"
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"You Belong with Me (Taylor's Version)"
Would I say "You Belong with Me" is Swift's most standout lyrical work as a songwriter? No, but it cemented her place in pop culture history as one of her first huge mainstream hits, and will remain a go-to karaoke fave forever.
Best lyric: "Dreaming of the day when you wake up and find / That what you're looking for has been here the whole time"
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"The Way I Loved You (Taylor's Version)"
To quote Cosmopolitan's Associate Shopping Editor Daisy Maldonado, "If you don't include 'The Way I Loved You,' I will personally be fighting." Points were made; this track off Swift's Fearless album was a fave of fans at the time of the album's release for its ~passionate~ lyrics and storytelling, which helped cement Swift's signature writing style early on.
Best lyric: "He can't see the smile I'm faking / And my heart's not breaking' / Cause I'm not feeling anything at all / And you were wild and crazy / Just so frustrating, intoxicating, complicated / Got away by some mistake."
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"Bad Blood (Taylor's Version)"
Taylor Swift's "Bad Blood" will go down in history as one of the defining cultural touchstones of 2014. This song has everything: betrayal, payback, a Katy Perry feud, and a video that hard-launched Swift's girl squad into the universe.
Best lyric: "Band-aids don't fix bullet holes / You say sorry just for show / If you live like that, you live with ghosts"
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"Delicate"
As successful, cool, and talented as Swift is, one thing she is not anymore is relatable. She's a literal billionaire. And yet, there's just enough self-doubt and emotional rawness peeking through in "Delicate" to convey the same dating insecurities many of us have felt at one point or another.
Best lyric: "My reputation's never been worse, so / You must like me for me"
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"Nothing New (Taylor's Version)" featuring Phoebe Bridgers
A guitar-driven ballad that was later released from the vault, "Nothing New" gives fans a raw look at Swift's fears as a young artist, aging into adulthood in an industry that values youth—especially in women—above all else. And it features Phoebe Bridgers, making it an instant sad girl music classic.
Best lyric: "I know someday I'm gonna meet her, it's a fever dream / The kind of radiance you only have at 17 / She'll know the way, and then she'll say she got the map from me / I'll say I'm happy for her, then I'll cry myself to sleep."
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"Getaway Car"
"Getaway Car" features some of the best storytelling on Reputation. In the upbeat pop song, Swift's lyrics are self-aware and revealing about the tangled dating webs she was highly criticized for during this time. Not only did it show some cheeky growth for her, it did so in major bop form.
Best lyric: "It was the best of times, the worst of crimes / I struck a match and blew your mind / But I didn't mean it and you didn't see it / The ties were black, the lies were white."
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"Last Kiss (Taylor's Version)"
"This song walked so 'All Too Well' could run," says Cosmopolitan Assistant News Editor Samantha Olson. It's true that "Last Kiss" is one of Swift's more gut-wrenching and honest breakup songs. But it also isn't without hope, as the lyrics suggest that Swift has finally gotten to the last stage of grieving a breakup: acceptance.
Best lyric: "So I'll watch your life in pictures like I used to watch you sleep / And I feel you forget me like I used to feel you breathe"
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"Mr. Perfectly Fine (Taylor's Version)"
Joe Jonas once again got his due on Swift's "Mr. Perfectly Fine," which was released as a vault track on Fearless (Taylor's Version). The exes might be cool now, but back in 2008 when this song was written, Swift was still reeling from their breakup, which made for epic songs like this.
Best lyric: "I've been pickin' up my heart, he's been pickin' up her / And I never got past what you put me through / But it's wonderful to see that it never phased you"
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"Wildest Dreams (Taylor's Version)"
"Wildest Dreams" might be the best song in Swift's "fantasy romance" subgenre, aka songs in which she creates these wild, romantic, dreamy relationships that are over as quickly as they began. It also features one of my absolute favorite Taylor Swift bridges ever.
Best lyrics: "You'll see me in hindsight / Tangled up with you all night / Burning it down / Someday, when you leave me / I bet these memories follow you around"
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"Enchanted (Taylor's Version)"
"Enchanted" perfectly captures the magic of those first meeting butterflies, and the joy of fantasizing a relationship with someone without the pressure of reality. The fact that this song was inspired by Owl City (aka Adam Young) just makes it even better.
Best lyric: "My thoughts will echo your name, until I see you again"
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"Long Live (Taylor's Version)"
One of Swift's greatest strengths as a songwriter is her ability to pinpoint a specific moment in time—whether a fleeting feeling, relationship, or life experience—and make it immortal in song form. Nowhere is that more evident than on Speak Now's final track, "Long Live."
Best lyric: "Long live all the mountains we moved / I had the time of my life fighting dragons with you"
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"Better Than Revenge (Taylor's Version)"
OK, I'm going to say something controversial: I like the original "Better Than Revenge" better than Taylor's Version. Am I a bad feminist? Maybe. But there's just something so delightfully petty and angry about the original lyric, "She's better known for the things that she does on the mattress." Swift understandably replaced the slut-shamey line for the song's re-release, which is great! We love growth! But there was also something kinda great about knowing that Swift wasn't always perfect in her writing (or dating outlook). But honestly, both versions slap, and the re-record illustrates Taylor's growth as an artist and a woman.
Best lyric: "I'm just another thing for you to roll your eyes at honey / You might have him, but I'll always get the last word"
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"We Are Never Ever Getting Back Together (Taylor's Version)"
Somehow, Swift managed to turn post-breakup anger and empowerment into one of the catchiest songs in recent memory, and I, for one, will never be mad at it.
Best lyric: "We are never, ever, ever, ever getting back together / Like ever"
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"Mastermind"
Swift has long been praised (and criticized) for being somewhat of a PR mastermind—leaving Easter eggs for fans to find, teasing her upcoming projects, relating her songs to her personal life, etc. So, it's fun to see her get cheeky with that persona in "Mastermind." Self-awareness from a celebrity is always a win in my book.
Best lyric: "I laid the groundwork, and then / Just like clockwork / The dominoes cascaded in a line / What if I told you I'm a mastermind?"
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"Cornelia Street"
We all know Lover is largely about Swift's 6-year relationship with Joe Alwyn, and ever since they broke up, all I can think of is how she swore in this song that if they weren't together, she'd "never walk Cornelia Street again." 😢 As one of the album's standouts, this one explores the magical (and very fragile) feelings of a new relationship in such a way that you'll feel like you fell in love on Cornelia Street, too.
Best lyric: "Barefoot in the kitchen / Sacred new beginnings / That became my religion"
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"Mirrorball"
Swift's songs about deep insecurities always stand out, and "Mirrorball" is the perfect example. With its soft, dreamy vibes, it sounds like it should be a love song, but it's actually more of a melancholic look at how self-sabotaging people-pleasers can be in relationships.
Best lyric: "I can change everything about me to fit in / You are not like the regulars / The masquerade revelers / Drunk as they watch my shattered edges glisten"
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"Would've, Could've, Should've"
The genre of female pop stars (aka Demi Lovato and Swift) who grow up and realize their past relationships with older men might have been more inappropriate or negative than they thought will always be 10/10 in my book. "Would've, Could've, Should've," a track from the 3 am edition of Midnights, reflects on a past traumatic relationship through heavy religious undertones and imagery illustrating the loss of innocence and youth. Not only do the lyrics and symbolism show off Swift's skill as a writer, but the song also proves she is the master of writing epic bridges.
Best lyric: "If clarity's in death, then why won't this die? / Years of tearing down our banners, you and I / Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first"
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"Don't Blame Me"
"Don't Blame Me" is one of the best songs off of Reputation, and is one of Swift's better vocal performances. I SAID WHAT I SAID. The synth pop track gives some major Hozier vibes, experimenting with a new sound for Swift that mashes electro pop with gospel and EDM in pure perfection.
Best lyric: "Echoes (echoes) of your name inside my mind / Halo, hiding my obsession / I once was poison ivy, but now I'm your daisy"
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"You're On Your Own, Kid"
"You're On Your Own, Kid" isn't a song about love or revenge, but rather a coming-of-age about the pain of growing up and how hard it can be to depend on yourself as an adult. From yearning for young love to sacrificing yourself in the name of your career, the song showcases Swift's maturing, which we've all watched play out on a very public stage. Most importantly, it realizes and acknowledges the one person who has got her to where she is today: herself, making it stand out not only on Midnights but also in Swift's entire catalog.
Best lyric: "'Cause there were pages turned with the bridges burned / Everything you lose is a step you take"
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"Red (Taylor's Version)"
Red is famous for being T-Swift's signature lipstick color and one of her fave descriptors when it comes to love (we see you, "Maroon"). But "Red," of course, is one of the songs that started it all—a catchy, upbeat tune about a love that burns bright and fast.
Best lyrics: "Moving on from him is impossible / When I still see it all in my head / In burning red"
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"Ivy"
Cosmopolitan's Senior Astrology Editor Erika W. Smith loves that "Ivy" is one of Swift's most literary tracks. Plus, "a yearning, star-crossed lovers storyline always gets me."
Best lyric: "I can't stop you putting roots in my dreamland / My house of stone, your ivy grows / And now I'm covered in you"
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"Fearless (Taylor's Version)"
With maturity comes complexity, and that shows in Swift's writing, but just because her more recent songs are more layered doesn't mean her older, more innocent songs like "Fearless" are any less magical. The title track off her second studio album embodies how even as a teenager, Swift was a pro at capturing the butterflies and magic of young love.
Best lyrics: "'Cause I don't know how it gets better than this / You take my hand and drag me head first / Fearless"
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"'Tis the Damn Season"
Swift takes a more subtle storytelling approach in "'Tis the Damn Season," which is probably why it's one of her most beloved. It's just vague enough for you to imagine yourself living it, and the romanticizing of the road less traveled is something we can all relate to every now and again. Plus, being able to make a hometown hookup sound like the most romantic "the one who got away" love story imaginable is a superpower.
Best lyric: "Time flies, messy as the mud on your truck tires / Now I'm missing your smile, hear me out / We could just ride around /And the road not taken looks real good now"
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"False God"
Swift's Lover era was full of upbeat, lovey-dovey songs, which makes the slower, bittersweet "False God," a song about sticking it out through the rough times, stand out.
Best lyric: "They say the road gets hard and you get lost when you're led by blind faith"
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"Forever & Always (Taylor's Version)"
I would consider "Forever & Always" one of the first Swift breakup bangers, and it's still just as fun to listen to now as it was when it was released in 2008.
Best lyric: "Cause it rains in your bedroom / Everything is wrong / It rains when you're here and it rains when you're gone"
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"Bigger Than the Whole Sky"
"Bigger Than the Whole Sky" might be one of Swift's most heartbreaking songs. It explores grief and loss through devastatingly poetic lyrics that immediately struck a chord with fans when it was released as a bonus track on Midnights. Though the singer never commented on the inspiration or meaning behind the song, many fans found comfort in its message while processing the loss of loved ones as well as their own miscarriage experiences.
Best lyric: "Every single thing I touch becomes sick with sadness"
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"Back to December (Taylor's Version)"
"Back to December" is one of the few positive post-breakup songs in Swift's catalog. The slow track is believed to be about her short-lived relationship with Taylor Lautner, and is a refreshingly vulnerable song in which Swift sings about her regrets and faults that caused the relationship to end.
Best lyric: "And then the cold came, the dark days / When fear crept into my mind / You gave me all your love and all I gave you was goodbye"
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"August"
"August" captures every adult's nostalgia for an adolescent love, whether they had one or not. Featured as part of the teenage love triangle trilogy Swift created on Folklore (along with "Cardigan" and "Betty"), this song is laced with the fleeting magic of a summer love. Case in point? It served as the perfect song to the second season of The Summer I Turned Pretty, which led to its even viral TikTok moment last year.
Best lyric: "Back when we were still changin' for the better / Wanting was enough / For me, it was enough / To live for the hope of it all"
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"Dear John (Taylor's Version)"
Swift's greatest skill is her ability to validate the experience of young women in song form, and she put that skill to great use on "Dear John," a song about what it's like to be played by an older man. She manages to balance scathing burns with emotional rawness flawlessly from beginning to end.
Best lyric: "All the girls that you've run dry have tired lifeless eyes / Cause you burned them out / But I took your matches before fire could catch me"
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"Betty"
"Betty" stands out in a robust catalog of work because it puts a twist on Swift's trademark storytelling. Instead of singing from her own perspective, she takes on the POV of a teenage boy struggling to apologize to his ex, Betty. It serves as part of a teenage love story trilogy on Folklore (also including songs "August" and "Cardigan"), the first time Swift experimented with this writing style—and it resulted in some of her best work.
Best lyric: "I'm only 17, I don't know anything / But I know I miss you"
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"Our Song"
"Our Song" was the third single off Swift's first album, and while it's definitely extremely country, it's also one of her first songs to cross over into the pop world. At the time, I was nowhere near being a country girlie, but this song made its way to me anyway. And I've loved it ever since.
Best lyric: "He's got a one-hand feel on the steering wheel / The other on my heart"
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"My Tears Ricochet"
I love when Taylor Swift goes scorched earth (see: "Better Than Revenge" and "Vigilante Shit"), but there's something even more satisfying about when she captures heaviness and heartbreak in a devastatingly beautiful way. That's the case with "My Tears Ricochet," a haunting song about betrayal that features some of Swift's greatest metaphors and symbolism.
Best lyric: "You know I didn't want to have to haunt you / But what a ghostly scene / You wear the same jewels that I gave you / As you bury me"
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"Style (Taylor's Version)"
Since Lover, Taylor Swift has moved away from teasing which famous ex-boyfriend inspired her newest hit, and that's probably for the best. That said, her unabashed use of "Style" (aka, her ex Harry Style's literal last name) will always be a force for good that brought us this absolute bop.
Best lyric: "And I should just tell you to leave, 'cause I / Know exactly where it leads, but I / Watch us go 'round and 'round each time"
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"Exile (feat. Bon Iver)"
Swift entered into a new era once again with the release of Folklore in 2020, and while the album includes many standouts, the most haunting of those is "Exile (feat. Bon Iver)." And, no, I'm not just saying that because of the excellent use of the song in the You season 3 finale.
Best lyric: "You're not my homeland anymore / So what am I defending now?"
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"Cruel Summer"
Fans b-e-g-g-e-d Swift to release "Cruel Summer" as a single when Lover first dropped in 2019, and they were right. It's basically your favorite early 2000s teen movie in song form. Proving its power? Four years (!!) after its release, "Cruel Summer" finally had its day and became Swift's biggest and longest-running radio hit single ever.
Best lyric: "And I screamed for whatever it's worth / 'I love you,' ain't that the worst thing you ever heard?"
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"Blank Space (Taylor's Version)"
Taylor Swift officially entered her pop era with "Shake It Off," the debut single off 1989, but "Blank Space" is the song that really sold it. The production, the music video, and, most importantly, the lyrics, which poke fun at her heartbreaker reputation, still hold up today. 10/10 perfect pop hit.
Best lyric: "'Cause darling, I'm a nightmare dressed like a daydream"
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"Fifteen (Taylor's Version)"
Teenage girls are used to having their experiences belittled by popular media, which is why Taylor Swift's "Fifteen" stands out as remarkable. Originally released back when the singer was in her country era, "Fifteen" is a bittersweet ballad about adolescence and friendship that every woman can relate to.
Best lyric: "And Abigail gave everything she had / To a boy who changed his mind / And we both cried"
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"All Too Well (10 Minute Version)"
The number one spot on this list should come as a surprise to no one. "All Too Well" has been a fan-favorite since its release on Red in 2012. The gutting lyrics that many of us can relate to all! too! well! (sry). The vulnerability. The BRIDGE. It's undoubtedly some of Swift's best lyrical work and storytelling. But then she decided to really spoil us with "All Too Well (10 Minute Version)" as a vault track for Red (Taylor's Version), managing to somehow top the original. The extended lyrics and verses proved that the power of Swift's songwriting lies in the fact that she can make 10 minutes feel like a captivating breeze of perfection.
Best lyric: "And you call me up again just to break me like a promise / So casually cruel in the name of being honest"
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