“You Win Again“ is a 1952 song by Hank Williams….which is in the style of a blues ballad that deals with the singer’s despair with his partner. Hank Williams recorded “You Win Again” on July 11, 1952….which was one day after his divorce from Audrey Williams was finalized…..and 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.”
“You Win Again” was released as the B-side to “Settin’ the Woods on Fire”….which was primarily because up-tempo dance number were preferable as A-sides for radio play….and for the valuable jukebox trade. Nonetheless, “You Win Again” peaked at # 10 on the Most Played in C&W Juke Boxes chart….where it remained for a single week. The song has been widely covered, including versions by Ray Charles, Jerry Lee Lewis, Roy Orbison, the Grateful Dead, Bob Dylan, Lefty Frizzell, Jerry Lee Lewis, George Jones, Gram Parsons, Townes Van Zandt, Keith Richards and the Rolling Stones, Glen Campbell, Martina McBride, Conway Twitty and Charlie Pride….just to name a few.