[citation needed] After performing as a backup singer, Shepard received her own recording contract and made her first chart appearance in 1987 with her duet with Dan Hill, "Can't We Try."

It saw the moderate commercial success of the single "Don't Cry Ilene", which peaked at number 17 on the Billboard Hot Adult Contemporary chart and remained there for 12 weeks.

Kelley decided during the performance that he wanted Shepard to record the soundtrack for his forthcoming television series Ally McBeal, having been looking for a singer to be the voice and inner thoughts of the character.

[1] Her version of Kay Starr's Christmas classic "(Everybody's Waitin' for) The Man with the Bag", after it was featured on a season 4 episode of Ally McBeal, became a popular holiday song.

In 2010, she provided vocals for "I Need You," whose music had been composed by James Newton Howard, for the film Love & Other Drugs.