The lyrics tell a story of a derelict (Washburn), chosen by a well-meaning charity for a wash-up and a meal. Washburn rejects the offer, though, preferring his jobless, drunken but easygoing lifestyle to a life of responsibility. He mentions, "I do believe I got it made".
The Monkees' version of "D.W. Washburn" was the first single they released after the second and final season of their series on NBC concluded. All their previous singles reached the #1, #2, or #3 positions from strong promotion through their use in various episodes; without this boost, the song became the band's first to miss the Top Ten in the U.S. Billboard charts, reaching #19. Micky Dolenz sings the song in a high falsetto, and is in the honky tonk style from the 1920s and 1930s.
The Coasters released their version of the song in July 1968. They had recorded the song on October 31, 1967 with Date Records. The B-side of the song was "Everybody's Woman."
A medley. "D.W. Washburn/L. David Sloane (A Good Man Is Hard To Find)" by the Hutch Davie Calliope Band, entered the Cashbox "Looking Ahead" survey on 8/25/68.
The Monkees continued to perform the song, during their 1980s and later reunions. One performance was on Nashville Now; a country music showcase.