After two years at UMass Lowell, he moved to Boston, where he worked in a silk screen shop and joined the proto-synth/punk band The Girls as a bassist,[1] with abstract painter Mark Dagley, avant-garde musician Daved Hild, and Robin Amos, founding member of Cul de Sac.

[3] His work has influenced many artists of his and the subsequent generation, including Nigel Cooke, Sean Landers, John Currin, Lisa Yuskavage and Glenn Brown.

Condo moved to Cologne, Germany, where he met and worked with several artists from the Mulheimer Freiheit group, including Walter Dahn and Jiri Georg Dokoupil.

[6] Several of Condo's most significant works from this period, such as Dancing to Miles (1985), which was included in the 1987 Whitney Biennial and is now in the collection of the Broad Foundation in Los Angeles, were painted in Haring's East Village studio.

Between 1985 and 1995 Condo lived and worked mostly in hotels and rented studios between Paris and New York, while continuing to exhibit extensively in the United States and Europe.

You sacrifice everything to this effect, particularly pictorial structure, which you systematically destroy, thus removing a protective guardrail, a frame of reference which might reassure the viewer, who is denied access to a stable set of meanings."

(Felix Guattari, 1990) Throughout his career as an artist, Condo's work has served as an influence and inspiration to contemporary writers including Burroughs, Guattari, Demosthenes Davvetas, Donald Kuspit, Wilfried Dickhoff, and Salman Rushdie, whose 2001 novel Fury includes a chapter inspired by Condo's 1994 oil painting The Psychoanalytic Puppeteer Losing His Mind.

[10] American fiction writer David Means also used a Condo painting, The Fallen Butler (2010), as inspiration for his short story "The Butler's Lament", which appears in the catalogue for the exhibition Mental States, a mid-career survey of the artist's paintings and sculptures organized by the Hayward Gallery, London, and the New Museum, New York, in 2011.

The final design, depicting a demonic caricature of the artist with a female phoenix on his lap and bottle in his hand, was even censored by iTunes, and the album cover is now a blurred version of the Condo painting.

[18] Condo's work has also been featured on the covers of the Phish album The Story of the Ghost (Elektra, 1998), Danny Elfman's Serenada Schizophrana (2006), and Franck Debussy Schumann by Dora Schwarzberg and Martha Argerich (AventiClassic, 2006), among others.

Most recently, Condo painted an abstracted portrait of the opera countertenor Anthony Roth Costanzo for the cover of his first album ARC, released in 2018 by DeccaGold and featuring recordings of works by Philip Glass and George Frideric Handel.

[19] In 2005 the Museum der Moderne Salzburg and Kunsthalle Bielefeld co-organized the exhibition George Condo: One Hundred Women, curated by Dr. Thomas Kellein.

In 2009 the Musee Maillol, Paris, organized the exhibition George Condo: The Lost Civilization featuring paintings, drawings, and sculpture created between 2003 and 2008.

The monograph published by Gallimard in conjunction with the exhibition featured new writings on the artist's work by Didier Ottinger, Bertrand Lorquin, and Massimiliano Gioni, as well as a reprinting of Felix Guattari's original text from 1990.

In 2013, Condo's large black-and-white banner featuring a court jester was installed on the façade of the Metropolitan Opera House, advertising the Met's new production of Verdi's Rigoletto.