Top 10 Saddest Taylor Swift Songs

“Speak Now” (2010)
We’ve all heard that same old, tired line about Taylor’s songwriting: that she only ever sings about hating her ex-boyfriends. “Back to December” was an early rebuttal of these shallow critiques, serving as an emotional, effusive apology to a spurned partner. Actor Taylor Lautner has gone on the record claiming that “December” is about him, and if so, we desperately want to know the Taylor-squared lore that led to this song being made. To be clear, we’re not complaining: “Back to December” is one of Taylor’s hardest-hitting breakup songs. Said Swift herself in a pre-“Speak Now” interview: “There was someone who was absolutely wonderful to me and I dropped the ball, and I needed to say all that.” Now, “Dear John,” on the other hand…

“Speak Now (Taylor's Version)” (2023)
It feels almost impossible to believe that “Speak Now” was released when Swift was just nearing 21 years of age. Her heartwrenching “Last Kiss” lyrics belie her youth, demonstrating the powerful wisdom of someone years older. “Last Kiss” is an emotional gut-punch, hitting you squarely in the chest with its recounting of a painfully unexpected breakup. The song captures the unresolved longing and heartache that come with a left-field parting, when you’re left to pick up the pieces while your ex-partner seems to be Mr. Perfectly Fine. Reckoning has long been one of Taylor’s specialties.

“Red (Taylor’s Version)” (2021)
Swiftie or not — chances are you’ve heard of this one. Rumors swirled for years around this stirring anthem, with fans claiming that an extended version with even juicier verses had been withheld from Swifties. Whether or not that’s true is still up for debate, but Taylor indulged fans by releasing the now-famous 10-minute version of “All Too Well” alongside other rerecordings from “Red.” And ask any Taylor fan: the nearly decade-long wait was well worth it. “All Too Well” quickly went from underrated fan-favorite to yet another one of her signature songs. The new “All Too Well” is the rare sequel that improves upon the original — even more bittersweet, open-hearted, and tearjerking this time around.

“Midnights” (2022)
We mentioned a little earlier that Taylor is no stranger to the music industry, with her first album having been released in 2006. But we’ve almost never heard her address her meteoric rise to fame in such stark, unambiguous terms. Compared by music critics to songs like “You Belong with Me,” “Fifteen,” and “Hey Stephen,” “You’re on Your Own, Kid” finds Taylor openly reflecting on how her fame has, for better or worse, changed her preexisting relationships. The song is an uncomfortable reminder that nothing lasts forever, and sadly but inevitably, all good things have to come to an end in order for new doors to open.

“Evermore” (2020)
Over the course of her career, Taylor became known not only for her mastery of songwriting, but also for her expansive, maximalist instrumental arrangements. However, when it came to “Folklore” and “Evermore,” the “Champagne Problems” singer took a radically different approach. This was, of course, partially necessitated by the limits imposed as a result of the COVID-19 pandemic. While we could’ve gone with “Tolerate It” or “Right Where You Left Me,” his song stands as a perfect example of Swift’s attempt at a more minimal sound, consisting only of her vocals and a bare-bones instrumental courtesy of co-producer Aaron Dessner. That decision allows Taylor’s vocals and rich, deeply felt songwriting to shine through — and leave us reaching for the nearest box of Kleenex.

“Lover” (2019)
This “Lover” deep cut, co-written and co-produced by Swift and Jack Antonoff, is a heartrending tribute to the singer’s mother Andrea. Specifically, the song conveys Swift’s hopeful optimism regarding Andrea’s multiple cancer diagnoses over the years. Even if you’ve never dealt with the disease on a personal level, it’s almost impossible to stay unmoved by the lyrics of “Soon You’ll Get Better,” which describe the difficulty Taylor faces with her mother’s illness and mortality. Featuring gorgeous backing harmonies courtesy of country legends the Chicks, “Soon You’ll Get Better” finds Taylor revisiting her roots in more ways than one.

“The Tortured Poets Department” (2024)
No one has ever faulted Taylor for being too relatable. “Loml,” a low-key highlight from “The Tortured Poets Department,” laments the demise of an all-too-brief relationship. We were tempted to go with “So Long, London” and “The Prophecy,” both from this album. That said, through her raw, bluntly sentimental songwriting, “Loml” is like a four-and-a-half minute journey right into her thought process. The song proves that, even after nearly 20 years in the limelight, Taylor Swift still has a remarkable gift for poetically describing her feelings of heartbreak. Clearly, Taylor knows better than anyone else that sometimes, wallowing in your sadness is the first (and most crucial) step to healing.

“Folklore” (2020)
Reportedly the first song written for “Folklore,” “My Tears Ricochet” finds Swift taking a stab at addressing her feud with Scooter Braun and Big Machine label head Scott Borchetta. However, the song is less about Braun and Borchetta specifically and more about Taylor’s bitter, conflicted feelings on the matter. Said Swift of the song, “All of a sudden this person that you trusted more than anyone in the world is the person that can hurt you the worst. Then all of a sudden the things that you have been through together, hurt.” “My Tears Ricochet” demonstrates Taylor’s singular ability to make her pain feel universal. Check out “This is Me Trying” if you’re looking for a good “cry-in-the-shower” song.

“Evermore” (2020)
Did you think you were out of the woods yet? Another addition to Swift’s canon of songs about female family members, “Marjorie” is a tribute to her maternal grandmother Marjorie Finlay, an opera singer by trade. The song finds Taylor mourning Marjorie, as well as lamenting the fact that she couldn’t get to know her better. As such, “Marjorie’s” chorus consists of a series of affirmations — life lessons, from Taylor’s grandmother to her. Featuring uncredited backing vocals from Bon Iver’s Justin Vernon, the song’s empowering nature is underscored by the bittersweet realization that its namesake didn’t live to hear it.

Before we unveil our top pick, here are a few honorable mentions.

“Red (Taylor’s Version)” (2021)

“Midnights” (2022)

“Folklore” (2020)

“Fearless (Taylor's Version)” (2021)

“Midnights: The Late Night Edition” (2023)

“Red (Taylor’s Version)” (2021)
Oof. It’s going to be hard to get through this entry without tearing up, but we’ll try. Although it might not be the #1 you would have expected, we think you’ll understand the logic behind placing “Ronan” at the top of our list. For this song, Taylor found inspiration from blogger Maya Thompson, whose 3-year-old son Ronan tragically died from neuroblastoma, a cancer of the nerve tissue, in 2011. Of course, writing a charity song intended to benefit the families of children with cancer is a noble pursuit. But how does one capture the feeling of mourning a child without having experienced it firsthand? Taylor answered this difficult question by sourcing the song’s lyrics straight from Thompson’s blog. Ultimately, that’s Taylor’s superpower: her seemingly endless well of empathy.

Do you agree with our picks? Which Taylor song makes you weep the hardest? Let us know in the comments!