In July 2006, Fiona Apple was riding high on the wave of her album *Extraordinary Machine*, which had been released the previous October. The live performance at the Charter One Pavilion in Chicago, as captured in the video, showcases her striking ability to blend emotional vulnerability with raw musical talent—a hallmark of her artistry. Interestingly, *Extraordinary Machine* had a bit of a tumultuous journey before its release, initially being shelved by her record label. But when it finally dropped, it was met with critical acclaim, reinventing Apple's sound and affirming her stature in the music industry. The live rendition of “Extraordinary Machine” not only highlights her signature piano-driven style but also brings forth that unique blend of angst and beauty that fans adore. It’s a moment where her vulnerability shines, making it clear why she resonates so deeply with her audience.