"Another Side of Bob Dylan" was recorded in a single night on June 9, 1964, according to "Bob Dylan: prophet, mystic, poet," during a period of immense change in the young Dylan's life, as many of the lyrics on the album make clear. First, there was the break-up of his long-term relationship with his partner Suze Rotolo, who famously featured alongside the songwriter on the cover photo of "The Freewheelin' Bob Dylan." Dylan had indulged in an affair with Joan Baez during their time performing together, which was "devastating" to Rotolo, per Reuters.
Rotolo recalled in her memoir, "A Freewheelin' Time," that their relationship soon collapsed after she and Dylan agreed to terminate her pregnancy. The difficult end of their relationship was captured in "Ballad in Plain D," a song that has been panned by critics as self-pitying and which Dylan later regretted, per "Revolution in the Air: The Songs of Bob Dylan 1957-1973."
1964 was also the year that Dylan first started experimenting with writing under the influence of hallucinogenic drugs according to the Dylan biographer Bob Spitz, and while the sound nor the content of "Another Side of Bob Dylan" can be said to be psychedelic in the way music would sound in the late 1960s, it is arguable that the famous refrain of "My Back Pages" — "I was so much older then, I'm younger than that now" — is indicative of a new visionary strain in Dylan's songwriting as outlined by Literary Hub.
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