Taylor Swift's Tearjerkers: Best Cry-Worthy and Popular Songs Ranking [2026]
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.
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Taylor Swift’s Tearjerker Songs: Top Cry-Worthy and Popular Tracks [2026] (1–10)
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.”
Blank SpaceTaylor Swift7rank/position
This song portrays the tumult of romance with humor and irony.
Taylor Swift cleverly turns the way the media treats her on its head, exaggerating the image of a woman who dates a lot.
The lyric about writing a new lover’s name on a “blank space” symbolizes the cycle of relationships.
Released in November 2014, it spent seven consecutive weeks at number one in the U.S.
It received high praise from critics and was nominated for a Grammy Award.
It’s a recommended track for those who’ve experienced heartbreak and want to take a closer look at themselves.
Long LiveTaylor Swift8rank/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.
Never Grow UpTaylor Swift9rank/position
This song, released in 2010 by an American country-pop singer who is also a singer-songwriter, has heartbreakingly poignant lyrics expressing a wish for a child not to lose their pure cuteness, not to bear the burdens of the world, and not to grow up.
Moreover, those lyrics blend with her sweet, unaffected voice to evoke an indescribable feeling.
22Taylor Swift10rank/position
A track included on the 2012 album Red is a bright pop anthem that celebrates the innocence and freedom of the early twenties.
Created by Taylor Swift in collaboration with world-renowned producers Max Martin and Shellback, the song portrays a wounded heart finding healing through time spent with friends.
Its breezy sound, blending elements of disco and 1990s rock, emphasizes anticipation for the new days ahead rather than the sadness of a breakup, and will gently support anyone facing the milestone of graduation.
It’s a song I recommend to all who want to carry the days spent with friends in their hearts and take a step toward tomorrow.