He is arguably best known for his character, seen as a drag incarnation, Kiki, an aging, alcoholic, and bitter chanteuse known for her raucous and edgy medleys of unusual cover songs. As Kiki, Bond performed with piano-playing sidekick, Herb played by Kenny Mellman, as part of the lounge act Kiki and Herb. Kiki and Herb came out of the queer activist and underground scenes in San Francisco with initial performances in the 1990s at Eichelberger's. Bond moved to New York City in 1994 and the act developed. A fictional biography of the duo is on their Facebook page. The show, fronted by Bond, met with critical success with each successive version and developed a cult following. They performed versions in London, at New York's The Knitting Factory and Carnegie Hall as well other venues. Their show Kiki & Herb: Alive on Broadway was nominated for a 2007 Tony for Special Theatrical Event. The duo broke up in 2008.
Bond also performed, with a backup band, the Freudian Slippers until 2001. Bond was namechecked in Le Tigre's prolific song "Hot Topic" on Le Tigre's self-titled debut. The song pays tribute to dozens of female visual artists, musicians, writers, feminists and others who have inspired them. Bond also appears, playing himself, in the film Shortbus (released October 2006), and, as Kiki, in Paul Festa's film Apparition of the Eternal Church.
In July 2009, Bond released a five track e.p. Pink Slip featuring four original songs (The New Depression, May Queen, The Puppet Song, Michael in Blue) and a cover of Radiohead's "Arpeggi/Weird Fishes"