Ah, Fiona Apple—what a force in music! On December 3, 1999, she performed "Fast As You Can" on the "Late Show with David Letterman," marking a pivotal moment during her career. This performance was part of the promotional push for her acclaimed sophomore album, *When the Pawn...*, which had released just a few weeks earlier, in November. This album was a powerful follow-up to her groundbreaking debut, showcasing her evolution as a songwriter and artist. Interestingly, Fiona's lyrics in *When the Pawn...* reflect a raw vulnerability that resonates deeply, a stark contrast to the polished pop sounds of the late '90s. One notable aspect of that performance was how comfortably she blended her classic angst with intricate melodies, accompanied by a tight band featuring Jebin Bruni on keys and Michael Lockwood on guitar. You can almost feel the air buzzing with her intensity, right? That blend of passion and musicality captured in that TV appearance remains a highlight for many fans. It's like she laid her heart out in front of the cameras, and who doesn't appreciate that raw honesty?