After performing in a handful of cover bands throughout high school and attending the Los Angeles Musicians Institute, Buckley moved to New York City in 1990. He went back to L.A. after seven months, then returned to somewhat reluctantly participate in a Tim Buckley tribute concert at Brooklyn's St. Ann's Church in 1991; his buzzed about performance led to a relocation to New York in 1992. He soon took up residence at the tiny cafe Sin-é in the East Village. His eclectic performances at Siné, which revealed as much of an affinity for Edith Piaf and Nina Simone as Bob Dylan and Led Zeppelin, led to a contract with Columbia Records in 1993. Live at Sin-é, a four song EP, was released while Buckley assembled a band to record his full-length debut, Grace.
Featuring Buckley originals such as "Last Goodbye" as well as a cover of Leonard Cohen's "Hallelujah," Grace sold only modestly but was warmly received by critics. He would tour behind the album for nearly three years. In mid-1996 Buckley began recording demos for his second album — to be titled My Sweetheart the Drunk — with producer Tom Verlaine. He intended to record the album itself with Grace producer Andy Wallace in Memphis, Tennessee, where Buckley had recently relocated. On May 29, 1997 — the night he was expecting his band to arrive from New York — Buckley and a friend were en route to a rehearsal space when they decided to take a break alongside the bank of the Wolf River channel of the Mississippi River. After Buckley jovially waded into the water fully clothed and began swimming, he was pulled under by the wake created by a passing boat; his body was spotted six days later by a riverboat passenger.
Following his death, Buckley's mother began to work closely with Columbia, followed by a move to SONY Legacy, on all affairs concerning his posthumous releases. The first was Sketches for My Sweetheart the Drunk, a double-disc set featuring the Verlaine-produced studio sessions and a selection of unfinished songs that Buckley had recently recorded on four-track. The live album Mystery White Boy followed in 2000, along with the DVD release Jeff Buckley — Live in Chicago. An extensive collection of Buckley's raw emotive power is compiled in the Live at Sin-é - Legacy Edition (released in 2003), a two-disc set of his early live performances at the East Village café and Grace - Legacy Edition, which also featured rare tracks and outtakes from live performances (released in 20014). In 2007, the album So Real: Songs From Jeff Buckley was released, featuring remastered tracks for hardcore fans and audiophiles. 2015 saw the release of long-anticipated, rare live performances and pre-Grace studio material titled You & I, and a freshly remastered release of the original Grace record was unveiled in 2016 to replace a previously compromised master of the album.