Growing up near Chicago, Christopher O'Riley took lessons in classical piano but played in rock and fusion bands throughout middle and high school before his family moved to Pittsburgh and he began experimenting with jazz. Still, it was to classical music that he turned as a profession, attending the New England Conservatory in Boston. His first releases followed in this vein, solo performances of works by composers like Schumann, Beethoven, Ravel, Busoni, and Stravinsky, and he even began hosting a radio program, From the Top, which was distributed by NPR and highlighted upcoming young classical musicians. However, it was when he branched away from classical that he began to gain wider attention in mainstream society. After hearing Radiohead's 1997 album OK Computer (albeit a few years after it came out), O'Riley became obsessed with the band and its sound and set about transcribing pieces for solo piano. True Love Waits: O'Riley Plays Radiohead came out in 2003, followed by Hold Me to This, another Radiohead tribute, in 2005. Around this same time, O'Riley, who didn't consider himself a composer, also became aware of the music of the late Elliott Smith. He took a similar liking to his music and released Home to Oblivion: An Elliott Smith Tribute in 2006, feeling that the singer's words could be given adequate respect and representation through his piano. Second Grace: Music of Nick Drake came out the following year.