The first three Casiotone for the Painfully Alone albums were made using only battery operated keyboards and electronics recorded to 4-track cassette. With 1999's Answering Machine Music, 2001's Pocket Symphonies for Lonesome Subway Cars (now collected onto one CD), and 2003's Twinkle Echo, Ashworth defined a hybrid strain of raw, emotional, and very homemade synth pop that was instantly recognizable as his own. Claustrophobic two-minute character studies shuddered with reverbed beats, blown-out chords, and simple but infectous melodies, all layered beneath Ashworth's sometimes funny but always heartbreaking lyrics.

Believing he had taken his self-imposed set of limitations to their logical conclusion, Ashworth expanded his sound with 2006's Etiquette. Etiquette removes the focus from a decidedly utilitarlian aesthetic to a broader production spectrum that finally gives Ashworth's personal, affecting song writing the space it deserves. In collaboration with producers and musicians like Jherek Bischoff (of The Dead Science and Degenerate Art Ensemble) and Jason Quever (The Papercuts and Pan American Recording Studio), the sound of Casiotone for the Painfully Alone has grown to include pianos, organs, strings, flutes, drums, and pedal steel guitars in addition to Ashworth's signature electronics and drum machines.