Songfacts®:

• Shepard first released this song on her 1989 debut album, but it was a duet version 10 years later with Indigo Girls' Emily Saliers that brought the song to the forefront. By 1999, Shepard had a regular gig playing herself in the hit TV series Ally McBeal, and she continued to record and perform during that time.
  
  Shepard tells us that the duet with Saliers didn't come quietly; it came screaming at her down the hallway of the Greek Theatre in Los Angeles. Vonda had just arrived at the theater for an Indigo Girls show, she explained in our interview.
  
  "And Emily came running down the hall, literally, like, 'Vonda f--king Shepard!' She said, 'Oh my God! I love you! I love the song 'Baby Don't You Break My Heart Slow,' she recalled.
  
  That night, Shepard took the stage with the Indigo Girls during their first encore to perform another song, "The Wildest Times of the World."
  
  Shepard and Saliers quickly bonded and ended up recording "Baby Don't You Break My Heart Slow" as a duet for the former's albums By 7:30 and Heart and Soul: New Songs from Ally McBeal (both released in 1999).
• Many of Shepard's songs are based on the many complicated Ally McBeal-like relationships she went through with various guys. Sometimes they are composites of ex-boyfriends, but this song was about one particular guy, and Shepard tells us that it was the only song she wrote about him. (Here's the full Vonda Shepard interview.)