Two new songs were added to "Greatest Hits": The first, "Tell Lorrie I Love Her" was written and recorded at home by Whitley for Morgan, originally intended as a work tape for Whitley's friend Curtis 'Mr. Harmony' Young to sing at Whitley's wedding. The second was "'Til a Tear Becomes a Rose", a 1987 demo taken from Tree that originally featured harmony vocals by childhood friend Ricky Skaggs. Lorrie Morgan, with creative control and license to Whitley's namesake, recorded her voice alongside Whitley's, and released it as a single, which rose to No. 13 and won them 1990's CMA award for Best Vocal Collaboration as well as a Grammy nomination for Best Country Vocal Collaboration.