Lang's career received a huge boost when Roy Orbison chose her to record a duet of his standard, "Crying", a collaboration that won them the Grammy Award for Best Country Collaboration with Vocals in 1989. The song was used in the Jon Cryer film "Hiding Out" released in 1987. Due to the success of the song, lang received the Entertainer of the Year award from the Canadian Country Music Association. Lang would win the same award for the next three years, in addition to two Female Vocalist of the Year awards in 1988 and 1989.