The image used for the cover of Dylan's groundbreaking second album The Freewheelin' Bob Dylan is one of the most memorable album covers of the 1960s. Suze Rotolo explained in an interview that this cover put the album contents into context ...Maybe no one would have known what the songs were about it if weren't for the album cover...the story is in the songs. Every song he has ever written about me. It's all there...

Various theories exist as to Dylan's reasons for changing the four tracks on this album. It has been widely assumed that following Dylan's boycott of the Ed Sullivan show on May 12th, 1963 after he had been prevented from performing the politically contentious Talkin'John Birch Society Blues, Columbia Records attorneys had asked him to revise the track listing accordingly. However, it seems that Dylan felt he'd outgrown the other three songs he changed, apparently he told an old friend at this time: ...there's too many old-fashioned songs [on the album], stuff I tried to write like Woody [Guthrie]. I'm going through changes. Need some more finger-pointin' songs in it, 'cause that's where my head's at right now. Rather than substitute only 'John Birch' with one of the eighteen outtakes left over from the 1962 sessions, Dylan decided to replace four songs [as evidenced by the deleted titles on both labels on the record in this lot] with songs he had written in England. Dylan visited England for the first time in December 1962 where he had embraced the English folk scene and been profoundly influenced by it.