In December 1998, when Elliott Smith performed "Waltz #2" on *Later... with Jools Holland*, he was at a pivotal moment in his career, having recently released his highly acclaimed album, *Either/Or*, earlier that year. This album marked a significant breakthrough for Smith, showcasing his introspective songwriting and unique sound. His appearance on Jools Holland's show introduced him to a wider audience in the UK, aligning with his growing reputation as a promising artist within the indie music scene. Notably, *Either/Or* features some of his most beloved tracks and is often credited with influencing a generation of singer-songwriters. This performance exemplified his intimate style, capturing the raw emotion of his live shows, which resonated deeply with fans and critics alike. Smith’s vulnerability in his music, highlighted during this performance, has become a defining characteristic of his artistic identity.