With friends and colleagues Jean-Michel Basquiat and Keith Haring (not to mention Julian Schnabel and David Salle), Condo was part of a small cadre of precocious New York-based artists who were intent on restoring faith in the possibilities for a progressive, and distinctively American, figurative painting style. Through their collective endeavors, they aligned the contemporary America art scene with the international Neo-Expressionist movement that came to prominence in the 1980s. Condo has made his own reputation through his willingness to explore combinations of different artistic styles within a single canvas. In his portraits, for instance, Condo is apt to combine the ceremony of the Old Masters with a mischievous humor that often draws on the conventions of pop cartoons; his aesthetic goal being to confound his viewer by employing the pop cartoon as a device that effectively debunks the idea that connects classical art with the intellect.
Condo has also described his artistic style as "psychological cubism," explaining that "Picasso painted a violin from four different perspectives at one moment. I do the same with psychological states". Many of his paintings recall thus the works by the likes of Willem de Kooning and Pablo Picasso and he uses this technique to explore themes relating to the macabre, the carnivalesque and the abject. In a third idiom to describe his practice, he has spoken of "visual choreography" whereby he gives visual form to music, his second great passion (after art).