In January 2000, during the time of the live recording on the Jon Brion Show, Elliott Smith was riding the wave of critical acclaim following the release of his album "Figure 8," which came out in April 2000. This album was significant as it showcased his move towards a more polished and expansive sound, a departure from the intimate, lo-fi aesthetic of his earlier works. The live performance reveals a captivating partnership with Jon Brion, who not only was a collaborator but also a key figure in Smith’s artistic growth during this period. Interestingly, "Figure 8" features themes of struggle and complexity, reflecting both Smith's personal battles and his evolving artistry, which is apparent in the depth of his live performance. This appearance undoubtedly solidified his status as an influential figure in the indie music scene at the turn of the millennium.