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, playing 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 in October 2000. A stripped-down acoustic effort, Skittish featured some of Doughty's most direct and personal lyrics, accompanied by his signature, syncopated guitar-playing style.
In addition to overcoming drug addiction and beginning work on a second solo album, Doughty continued to do solo tours and was heard contributing vocals to BT's club hit "Never Gonna Come Back Down," and collaborating with John Flansburgh of They Might Be Giants for a CD that accompanied an issue of McSweeney's Quarterly Concern. He also composed the soundtrack to a trailer for New York City's Gen Art Film Festival.
In July 2002, Doughty released the limited-edition live album Smofe + Smang: Live in Minneapolis. It featured a large selection of solo material as well as Soul Coughing classics. A book of poetry entitled Slanky, which was initially self-released in 1995, also coincided with the live album. In 2003, more solo work surfaced in the form of the Rockity Roll EP, which was then combined with the Skittish album and re-released with a handful of bonus tracks when Doughty signed to ATO Records in 2004. In 2005, Doughty released his first solo effort to feature a band, Haughty Melodic, which contained fleshed-out studio versions of several songs debuted on Smofe + Smang, and 2008's Golden Delicious followed suit. The latter album cracked the Billboard 100, Doughty's first solo release to do so, and he quickly returned in 2009 with another record, Sad Man Happy Man.
In 2011, he released the full-length Yes and Also Yes on his own Snack Bar label. In 2012, Doughty released a second book,The Book of Drugs, a memoir about his life with Soul Coughing and his struggles with addiction, as well as the live album The Question Jar Show and The Flip Is Another Honey, which featured Doughty covering artists from Thin Lizzy to Randy Newman. Hip-hop producer Good Goose helped Doughty revamp a set of Soul Coughing material following a successful spring 2013 PledgeMusic campaign, which helped him raise funds for the sessions. The lengthily titled release, named after every track that appears on the album, arrived in September of that year. The singer returned in 2014 with a pair of releases, including Live at Ken's House, which featured the versions of the Circles Super Bon Bon... songs Doughty played with a full band on tour, and Stellar Motel, an album of new material that found him continuing to fuse dance music and hip-hop into his singer/songwriter sound. ~ Lee Meyer, Rovi