Taylor Swift's Tearjerkers: Best Cry-Worthy and Popular Songs Ranking [2026]

FifteenTaylor Swift1rank/position

Taylor Swift – Fifteen

This ballad from the album Fearless, which sings about memories of being fifteen with a best friend, gently observes the growth of a girl who begins high school with a fluttering heart yet faces the disappointment of first love and her friend’s heartbreak.

The backstory—that Taylor Swift wrote the lyrics based on real experiences with her best friend Abigail, with Abigail’s permission—makes it even more moving.

Set to country-pop centered on acoustic guitar, its words unfold like reading aloud from a diary over a near album-long runtime of 4 minutes and 54 seconds, and each line really resonates.

Released as a single in August 2009, it also tied in with a project supporting teen charitable activities.

It’s a song you’ll want to listen to when you feel nostalgic about your high school days or want to revisit the bittersweetness of youth.

White horseTaylor Swift2rank/position

Taylor Swift – White Horse

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.

We Are Never Ever Getting Back TogetherTaylor Swift3rank/position

Taylor Swift – We Are Never Ever Getting Back Together

It’s the hugely popular song “We Are Never Ever Getting Back Together” by Taylor Swift.

It’s also well-known as the theme song for the hit Japanese TV show Terrace House, and it’s very popular among teens, so it’s recommended for high school students.

Back To DecemberTaylor Swift4rank/position

Taylor Swift – Back To December

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

Taylor Swift – Love Story

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.