The title comes from the opening stanza of Dylan's "Desolation Row": "They're selling postcards of the hanging/ They're painting the passports brown."

Seven of the songs on the album originally appeared on the Dylan albums Bringing It All Back Home and Highway 61 Revisited; the remaining three represent Blonde on Blonde, John Wesley Harding, and the Leon Russell session that produced "Watching the River Flow" for the Greatest Hits II double-LP.

Aside from being from among his most critically revered rock albums, the seven songs date from 1965, the year the long strange trip of the Grateful Dead began.

Conspicuously absent from the compilation is "Knockin' on Heaven's Door", a song the Dead performed more than 170 times.

Conversely, "It Takes a Lot to Laugh, It Takes a Train to Cry" was performed a few times in the early 1990s, and only once in the 1970s – in the version included here, the Dead are accompanied by Dickey Betts and Butch Trucks, of the Allman Brothers Band.