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"You're Gonna Make Me Lonesome When You Go" is a song by Bob Dylan. Recorded in September 1974, it appeared as the fifth track on Dylan's album Blood on the Tracks, released in January 1975.
The song's lyrics have brought forth multiple interpretations—from the idea that they are confessional, to Dylan's claims that the album was inspired by literature, to the lyrics being called Dylan's most masterfully written love poem. Many believe the song describes Dylan's relationship issues with his wife during the time when they were separated. Additionally, Ellen Bernstein, a girlfriend of Dylan's in 1974 while he was separated from his wife, claims that the song was about their relationship. However, in interviews Dylan claimed the song was inspired by literature. Rolling Stone reported that in Dylan's memoir, Chronicles: Volume One, "Dylan was assumed to be referring to Blood on the Tracks when he wrote: “I would even record an entire album based on Chekhov short stories. Critics thought it was autobiographical – that was fine”.
The song was one of a few Dylan attempted to record with a full band (Eric Weissberg and Deliverance) at the album's initial September 1974 sessions in New York. Multiple versions were attempted, including a slow ballad arrangement, but ultimately Dylan opted - as he did with most of the tracks from these sessions - for a near-solo acoustic arrangement backed only by Deliverance bassist Tony Brown. The complete recording session of "You're Gonna Make Me Lonesome When You Go" was released in 2018 on the deluxe edition of The Bootleg Series Vol. 14: More Blood, More Tracks, with one outtake appearing on the 1-CD and 2-LP versions of that album.
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