Nelson lost the money he made from his song-writing royalties by financing concert tours that were generally unsuccessful and unprofitable.

Considered one of country music's first concept albums, Yesterday's Wine is the story of the "Imperfect Man", from the moment he is born to the day of his death.

The album failed to reach the charts, and a frustrated Nelson decided to temporarily retire from music, while still under contract to RCA Records.

By the fall of 1964, Nelson had moved from Monument Records to RCA Victor, under the leadership of Chet Atkins, signing a contract for US $10,000 per year.

[6] On May 1–2, he wrote nine songs, combining new ones with previous material from his repertoire, such as "Family Bible", to create the concept for the album.

[7] In his 2015 autobiography, Nelson reminisced about this turbulent time in his life: "I looked up and simply began asking questions.

According to Nelson's biographer, Joe Nick Patoski, the new material portrayed "an idea that was so far-out that when it came time to record in early May, 1971 producer Felton Jarvis had no choice but to let the tapes roll".

"Yesterday's Wine" finds the character drinking in a bar, talking to the regulars about his life, and reflecting on aging.

[17] In 2015, Nelson recalled the opinion of one of the label's executives, who told the singer "It's your fuckin' worst album to date".

[18] Nelson added that another member of the label felt that the record was "some far-out shit that maybe the hippies high on dope can understand, but the average music lover is gonna think you've lost your cotton-pickin' mind.

He later wrote in his autobiography, "I think it's one of my best albums, but Yesterday's Wine was regarded by RCA as way too spooky and far out to waste promotion money on.

[24][25][26] Meanwhile, author Michael Streissguth felt that Yesterday's Wine "tried to be a concept album, but it lacked a clear thread, despite Willie's claim to the contrary.

He formed a new band and performed in local venues, as his act was rejuvenated by the burgeoning hippie scene of the city.

"[33] Nathan Bush described Yesterday's Wine for The New York Times as "the last and best of [Nelson's] Nashville albums", saying that it was "Organized in the manner of an epic poem, each cut a metaphor in the journey through life ... it was Nashville's first fully conceived concept album, and nobody knew what to make of it.

"[34] Rolling Stone wrote: "[Yesterdays Wine] is the first of his bold, conceptual departures from country's hits-plus-filler norm.

Rather than tack rock guitar riffs onto modern honky-tonk sagas, Nelson absorbed the innovations of Bob Dylan and the singer-songwriters into his own distinct style.

"[35] The Fort Worth Star-Telegram welcomed it as "the usual heady stuff expected from this unique song stylist.

[36] San Antonio Express-News considered that Nelson's "tearful voice" did "an excellent job in getting the message driven across in a collection of soft ballads".

The review described Nelson's songwriting as "deft of handling meaningful words" in "Family Bible", and his "mastery of the lyrics" on "Summer of Roses" and "December Day".

Nevertheless, he made a few landmark recordings while he was with that company ... Few of the songs on Yesterday's Wine are well-known Nelson compositions, but all are minor masterpieces".

"Yesterday's Wine" has been reissued on CD numerous times; in 1997 by Justice Records, a Houston, Texas–based independent label, and in 2003 by BMG Heritage.

In 2010, Sony reissued "Yesterday's Wine" as part of a triple disc boxed set, along with Red Headed Stranger and Stardust.