‘All Too Well’ [10 Minute Version] (2021)

This heart-wrenching break-up ballad finally came to Taylor after a six-month writing block that followed a particularly traumatic end to a relationship. It's a fan favorite and the song from Red that Taylor has always characterized as the toughest to write.

The song, written again with Liz Rose, is widely considered to be about Jake Gyllenhaal, whom Taylor briefly dated in 2010; a hypothesis that Swifties leap on at every opportunity.

"All Too Well" is the song that can be played repeatedly without becoming monotonous. It's another painful story about two lovers who are no longer together and reminiscing about what they used to have. Her narrative skills are on full display in this song, and her heartfelt melodies and words never fail to bring tears to my eyes. Her voice has a strong but gentle tone to it. Because of the quality that it gives in every syllable, this song will go down in music history for all time.

Album: “Red (Taylor’s Version)”

Songwriters: Taylor Swift, Liz Rose

Accolades: This expansion of the song she originally recorded in 2012 debuted at number-one on the Billboard Hot 100, making it Swift’s eighth chart-topper and the longest number-one song in Billboard history.