"When She Loved Me" is a song written by Randy Newman for Disney and Pixar's animated film Toy Story 2 (1999), and recorded by Canadian singer Sarah McLachlan. The song reveals the backstory of Jessie, a toy cowgirl, as she reflects upon her defunct relationship with her original owner, by whom she was outgrown. Heard in the film during a flashback sequence, the filmmakers decided to incorporate a song into the montage during which Jessie details her backstory to Woody after multiple attempts to show the character relaying her experience verbally proved unsuccessful.

Newman initially felt that the song was inappropriate, doubting that young children would be interested in it; he changed his mind after screen tests showed optimistic results. The song was offered to McLachlan after Newman and the filmmakers agreed that the ballad was more appropriate for a female artist. Despite some hesitation from her management, McLachlan greatly enjoyed the ballad and agreed to record it upon hearing Newman's demo, finding herself drawn towards its melancholy nature. Musically, "When She Loved Me" is an emotional pop ballad backed by simple piano accompaniment. Various interpretations of the song's lyrics and themes have been offered; while written primarily about the pain felt upon losing a platonic friend, "When She Loved Me" has also been interpreted as a love song, while some music journalists consider the track to be a metaphor for children inevitably growing up and becoming independent from their parents.

"When She Loved Me" has garnered critical acclaim from film and music critics, who found the song to be both moving and heartbreaking, praising Newman's songwriting and McLachlan's vocal performance. "When She Loved Me" won a Grammy Award for Best Song Written for a Motion Picture, Television or Other Visual Media. The song was nominated for Golden Globe and Academy Awards for Best Original Song but lost both to "You'll Be in My Heart" from Disney's Tarzan (1999). "When She Loved Me" has since earned a reputation as one of the saddest sequences in both Pixar and Disney films, as well as one of the saddest film songs ever written. The song has been covered by several artists, including Steve Tyrell, Bridgit Mendler and the musical group Steps.