“Cry, Cry, Darling” was written by Jimmy Newman and J. D. “Jay” Miller, the record man whose studio on North Parkerson Avenue in Crowley, Louisiana, had been cutting Newman’s records for Miller’s Feature label since 1951. Newman, born in High Point, Louisiana, in 1927, first recorded it there in the spring of 1953 with his band, the Rhythm Boys. That version came out around June 1953 on Khoury’s 630, with “You Didn’t Have to Go” on the other side.
Miller persuaded Fred Rose in Nashville to take an interest in the young singer, and Newman signed with Dot. About September 1953 he re-recorded both songs at Rose’s house on Woodmont Avenue in Nashville. Chet Atkins and Billy Byrd played guitar, Don Helms steel, Jerry Rivers fiddle, Ernie Newton bass, and Rose himself played piano. Dot issued the pair as Dot 1195 in February 1954. It became Newman’s first hit, reaching No. 4 on Billboard’s country and western juke box chart in May and staying on the charts for eleven weeks, and it won him a regular place on the Louisiana Hayride in Shreveport. Newman cut it again for Dot in Nashville on 29 September 1957, for an album.
The lyric is a promise of tears. If she leaves him “with the blues,” he will cry, cry; his eyes would “cry and never dry,” and when shadows creep he will “weep all night.” For him there’ll be “no moonlight” if they ever part, because “you’re the one that’s in my heart.”
Bill Monroe and his Blue Grass Boys recorded the song in Nashville on 14 May 1957 at Bradley Film & Recording, with Monroe singing lead and playing mandolin. Leslie Sandy played guitar, Don Stover banjo and Bessie Lee Mauldin bass, and there were three fiddles: Tommy Jackson, Gordon Terry and Dale Potter. It opened the 1958 Decca album Knee Deep in Blue Grass. Later bluegrass recordings include Laurie Lewis on Restless Rambling Heart (Flying Fish, 1986), with Tim O’Brien on guitar and mandolin; the Johnson Mountain Boys on Requests (Rounder, 1988), with Dudley Connell singing lead; Lou Reid on When It Rains (Sugar Hill, 1991); and Ricky Skaggs’s Big Mon (2000), where Dolly Parton and Lee Ann Womack join Skaggs on vocals. Chris Thile and Michael Daves recorded it as a mandolin-and-guitar duet at Third Man Studios in Nashville in January 2011 for Sleep with One Eye Open (Nonesuch).