Toychestra began as a once-off experiment in 1996 at a women's festival of experimental music at Hotel Utah in San Francisco.

[2] They dressed up in "dime-store costumes: bridal gowns, superhero outfits, and cowgirl regalia" with "future-shock hairdos and fluorescent wigs".

"[4] Composer Dan Plonsey from the San Francisco Bay Area Improv Scene first got to know Toychestra in 1998 when he booked them at his Beanbender's music venue in Berkeley, California.

He liked their eccentric style and decided to combine their creative talents with those of fellow Bay Area Improv Scene member and experimental guitarist, Fred Frith.

[4] Plonsey wrote a concerto for electric guitar and toy orchestra for Toychestra and Frith to perform,[4][5][6] and it was recorded and released in 2004 on a CD, What Leave Behind.