[9] In The Village Voice's annual Pazz & Jop critics poll for the year's best albums, The Lonesome Jubilee finished at No.

[10] "We were on the road for a long time after Scarecrow, so we were together a lot as a band," Mellencamp said in a 1987 Creem Magazine feature.

At one point, The Lonesome Jubilee was supposed to be a double album, but at least 10 of the songs I'd written just didn't stick together with the idea and the sound we had in mind.

"[11] On October 30, 1986 – during the period in which The Lonesome Jubilee was being recorded – Mellencamp's uncle Joe died of cancer at the age of 57, which greatly influenced the album.

The original working title of the album was Bobtown, because his grandparents had lived in that small Indiana community after they were married.

[2] The sound on the album was a departure from Mellencamp's previous albums and included many traditional folk and country instruments in order to make his audience aware of the "once-familiar social landscape" of folk music.

I showed it to Larry (Crane) and he said, 'That's a good little, uplifting story' – so we arranged it into a song and put it on the record.

"[11] The cover art for the album was photographed by Skeeter Hagler and featured Mellencamp sitting next to an older blue-collar working man.

According to Casey Kasem on his American Top 40 broadcast for the week ending January 30th, 1988, Mellencamp paid $300 to rent the tavern for the photo shoot.

The older working man seated next to Mellencamp at the bar is Woodrow "Woody" Baker (1914–2009), a welder recommended for the shoot by the tavern's bartender.