In September 1996, Fiona Apple was on the cusp of exploding into the music scene with her debut album, *Tidal*. This was a thrilling time for her—just months after the album's release in July, it began to garner critical acclaim and commercial success. The live performance of “Sleep to Dream” at the Troubadour in West Hollywood captured Apple's raw, emotive energy and showcased her distinctive voice, which was already making waves for its depth and vulnerability. It's fascinating to think about how Apple, only 19 at the time, was pouring her heart into every note amidst the pressures of newfound fame. Moreover, *Tidal* featured hits like “Criminal” and “Shadowboxer,” songs that would soon define her artistic identity. This performance is a snapshot of a pivotal moment—a blend of youthful intensity and profound artistry that hints at the incredible evolution Apple would continue to experience throughout her career.