In the mid-'90s, things were looking pretty good for Jeff Buckley. Although his 1994 debut album, Grace, hadn't been a blockbuster, it was a massive critical success. Up on the record's release, Buckley seemed to become the favorite newcomer for rock's elite, earning praises from Bono to Jimmy Page to David Bowie to Bob Dylan, who called him "one of the great songwriters of this decade."

While Buckley toured incessantly, his album eventually went gold in France and Australia and began to sell better in the U.S. as well. After two years of touring, in 1996, Buckley began working on his follow-up album in New York. As he was writing, he helped Patti Smith on her record, Gone Again, and met former Television guitarist Tom Verlaine – who agreed to produce Buckley's next CD. In New York City, Buckley began testing out songs for the upcoming record (to be titled My Sweetheart, the Drunk) at live shows. Lou Reed attended one, and told Buckley he'd like to work with him in the future.

In '96 and early '97, Buckley and his band began laying down tracks with Verlaine producing, but Buckley wasn't happy with the results. He felt a change of scenery might be in order and moved to Memphis in February. The singer rented a shotgun shack in Memphis and planned to record at Easley McCain Recording.

Verlaine and Buckley's band soon joined him in Memphis to take another crack at some sessions, but the magic still wasn't there. Buckley called upon Grace producer Andy Wallace to replace Verlaine and sent his band back to New York while he continued to work on writing and demos in Memphis. In the meantime, Buckley continued to test out his new songs live, playing regular gigs at Barrister's, a downtown bar.

He sent his demos to his band, who were thrilled with the results and excited to begin work on the songs. Arrangements were made for the musicians to fly in on May 29, 1997. Sadly, the day would prove a tragic one and the band would never see Buckley alive again.