Hank Williams recorded "You Win Again" on July 11, 1952—one day after his divorce from
Audrey Williams was finalized. Like "
Cold, Cold Heart," the song was likely inspired by his tumultuous relationship with his ex-wife, as biographer
Colin Escott observes:
It might have been no more than coincidence, but, in the absence of hard evidence to the contrary, the songs cut that day after Hank's divorce seem like pages torn from his diary...Its theme of betrayal had grown old years before Hank tackled it, but, drawing from his bottomless well of resentment, he gave it a freshness bordering on topicality.
In Williams' original draft, the song had been titled "I Lose Again" but was reversed at producer
Fred Rose's insistence. The song's memorable opening line, "The news is out all over town," begins the story of an utterly defeated narrator who cannot bring himself to leave his love despite her infidelities. It was recorded at
Castle Studio in
Jerry Rivers (fiddle),
Don Helms (steel guitar), and Harold Bradley (rhythm guitar), while it is speculated that
Chet Atkins played lead guitar and Ernie Newton played bass.
"You Win Again" was released as the
B-side to "
Settin' the Woods on Fire", primarily because up-tempo, danceable numbers were preferable as A-sides for radio play and for the valuable jukebox trade. Nonetheless, "You Win Again" peaked at number ten on the Most Played in C&W Juke Boxes chart, where it remained for a single week.
Tommy Edwards released the song for MGM on the same day as Williams and it rose to #13 on the pop charts in the fall of 1952.
In the early 1970s,
Mason Proffit recorded a slow, country rock version of the song on their album Rockfish Crossing.
Roy Orbison recorded it for his Hank Williams tribute LP in 1970.
Grateful Dead played the song numerous times on tour during 1971 and 1972. A live version recorded May 24, 1972 at Lyceum Theatre, London appears on the album Europe '72.Tracy Nelson recorded it on the 1969 album "Mother Earth Presents Tracy Nelson Country"