Before emerging as a solo artist, M. Doughty (first name: Michael) was best known as the frontman of the unique avant-garde group known as Soul Coughing. Spawned in 1992, Soul Coughing was formed after Doughty met his bandmates (Yuval Gabay, Sebastian Steinberg, and Mark de Gli Antoni) while working as a doorman at the Knitting Factory, a staple of New York City's hip underground music scene. Soul Coughing signed to Slash/Warner in 1993 after making a name for themselves on the local scene and attracting the attention of music labels with their fusion of ock, Doughty's beatnik-inspired lyrics, and elements of hip-hop and electronic music. Releasing their first of three albums the following year, Soul Coughing enjoyed only moderate commercial success over the next six years with the singles "Super Bon Bon" and "Circles." However, their unclassifiable music style kept Soul Coughing apart from the mainstream as the initial boom of alternative rock in the early '90s soon subsided considerably.

In March 2000, the members of Soul Coughing split up to work on their own side projects. Shortly after the breakup, Doughty, who had been writing as a columnist for New York Press on the side, embarked on a solo acoustic tour consisting of material from a then-unreleased solo album recorded in 1995, entitled Skittish. After bootleg copies of the album surfaced on the file-sharing network Napster, Doughty released an official version of Skittish on his website (/www.superspecialquestions.com) in October 2000. A stripped-down acoustic effort as opposed to the sonic abundance of Soul Coughing, Skittish features some of Doughty's most direct and personal lyrics accompanied by his signature syncopated guitar-playing style.