![Taylor Swift’s Tearjerkers: Best Sad Songs and Most Popular Tracks Ranked [2025]](https://i.ytimg.com/vi/D1Xr-JFLxik/sddefault.jpg)
Taylor Swift’s Tearjerkers: Best Sad Songs and Most Popular Tracks Ranked [2025]
Even women who are usually giving it their all have times when they just want to cry.
Here, we’re introducing a selection of Taylor Swift’s most popular songs—beloved by many women—that are especially moving and guaranteed to bring on the tears.
Taylor Swift’s Tearjerker Songs: Top 10 Most Emotional and Popular Tracks [2025] (1–10)
White horseTaylor Swift1rank/position
The queen of love songs, Taylor Swift, delivers a tear-jerking classic with “White Horse.” It’s a song about longing for a movie-like romance, only to find that real life doesn’t unfold like a dream—and even the prince you believed in ends up breaking your heart.
It’s a message that any woman who’s ever yearned for love can relate to at least once.
fifteenTaylor Swift2rank/position
Taylor Swift is a singer-songwriter who debuted with an album at the young age of 16 in 2006, grew from a young country star into a global pop icon, and continues to lead the scene even now in the 2020s.
While she’s often associated with being a master of love songs, the track introduced here, “Fifteen,” is included on her second album, Fearless, released in 2008.
It’s a classic she wrote as a message to a dear friend, reflecting on herself at 15.
With a fresh feel that sits between country and pop, it’s in simple songs like this that her true talent as a songwriter really shines through.
It’s a moving song that resonates with kids turning 15 and with adults who were 15 long ago.
By the way, the woman who appears in the music video is Abigail herself—Taylor’s best friend, who also appears in the song.
We Are Never Ever Getting Back TogetherTaylor Swift3rank/position
It’s a song that became a hot topic after being used as the theme for the popular show Terrace House.
Many of you have probably heard it.
The song portrays, from a woman’s perspective, a breakup with a selfish man.
The firm resolve to never get back together again conveys a strength that feels distinctly feminine.
Back To DecemberTaylor Swift4rank/position
A track from her third studio album, Speak Now.
In this song, Taylor Swift apologizes for ruining her relationship with her ex-boyfriend.
It is said that this “ex-boyfriend” refers to American actor Taylor Lautner.
Love StoryTaylor Swift5rank/position
A signature song by Taylor Swift inspired by Shakespeare’s Romeo and Juliet.
Its movie-like narrative—overcoming a difficult romance to reach a happy ending—is especially striking.
Released in September 2008, the track became a major hit as the lead single from the album Fearless, peaking at No.
4 on the U.
S.
Billboard Hot 100 and selling over 18 million copies worldwide.
Swift’s delicate vocals, paired with a beautiful melody woven from acoustic instruments like banjo and fiddle, are sure to resonate with anyone struggling with love.
RedTaylor Swift6rank/position
Taylor Swift often releases breakup songs, and this one turns the emotions of heartbreak and the memories from when they first met into colors.
Because it was such a memorable relationship with intense feelings, she reportedly titled the song “Red.”
Long LiveTaylor Swift7rank/position
Taylor Swift is a globally popular singer-songwriter.
While she now releases a wide range of tracks, including dance music and pop, she originally started out as a country musician.
“Long Live” is a song that lets you appreciate that side of her.
Although the lyrics are somewhat abstract, its theme of taking on new challenges struck a chord with listeners, and it has become known as a classic graduation song.