American Songwriter has rounded up three pop breakup anthems from the 1990s that remain enduringly popular, regardless of listeners' current relationship status. The list highlights ballads and tracks that captured heartbreak, betrayal and lingering attachment, songs that have since become staples at weddings, funerals and other emotional milestones.

The selections span different styles within the genre, from tender yearning to sharp-tongued kiss-offs, showing the breadth of ways 90s pop tackled the end of a relationship.

– "How Do I Live" by LeAnn Rimes — written by Diane Warren, a yearning ballad also recorded by Trisha Yearwood, later described by Rimes as tapping into society's "co-dependency nerve"
– "You Oughta Know" by Alanis Morissette — a scathing diss track from Jagged Little Pill aimed at an ex Morissette calls "Mr. Duplicity", though she has never confirmed his identity
– "Ex-Factor" by Ms. Lauryn Hill — a Top 40 pop and R&B hit that peaked at number seven on the Hot R&B/Hip-Hop Songs chart, noted for its two-chord structure and vivid depiction of a crumbling relationship