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"When You Say Nothing at All" is among the best-known hit songs for three different performers: Keith Whitley, who took it to the top of the Billboard Hot Country Singles chart on December 24, 1988; Alison Krauss, whose version was her first solo top-10 country hit in 1995; and Irish pop singer Ronan Keating, whose version was his first solo single and a chart-topper in the United Kingdom and Ireland in 1999. "When You Say Nothing at All" entered the Hot Country Singles chart on September 17, 1988, at No. 61, and gradually rose to the top, where it stayed for two weeks at the end of the year. It was the second of five consecutive chart-topping singles for Whitley, who did not live to see the last two, as he died on May 9, 1989 of alcohol poisoning. "Keith did a great job singin' that song," co-composer Schlitz told author Tom Roland. "He truly sang it from the heart." In 2004, Whitley's original was ranked 12th among CMT's 100 Greatest Love Songs.
In 1995, Alison Krauss covered the song with the group Union Station for a tribute album to Whitley titled Keith Whitley: A Tribute Album. The single release featured "Charlotte's in North Carolina," one of several previously-unreleased tracks sung by Whitley on the album, as the B-side. After Krauss's cover began to receive unsolicited airplay, BNA Records, the label that had released the album, issued Krauss' version to radio in January 1995. That version, also featured on Krauss' compilation Now That I've Found You: A Collection, peaked at No. 3 on the Billboard Hot Country Singles & Tracks chart, and a commercial single reached No. 2 on the same magazine's Hot Country Singles Sales chart. Krauss' recording won the 1995 CMA award for "Single of the Year".