George Condo’s The Secretary emerges from the shadowy grandeur of an Old Master portrait. Her face is twisted into a toothy grimace. She sports wild, lavender-coloured hair and a red dress with a white collar, perfectly tailored to her asymmetrical shoulders. A red apple – as shiny as her round, clownish nose – is balanced on her head. An arrow pierces her temples. This startling, beguiling figure is a signature example of Condo’s unique approach to portraiture, which is informed by a complex dialogue with art history. Clashing disparate references from Rembrandt to Picasso, Basquiat, American pop culture and the visual language of cartoons, Condo’s works dismantle the fantasies and artifices inherent in figurative painting. A cacophony of signals compete, pushing the image into a strange, disconcerting realm that we’re not quite sure how to read. The ‘secretary’ joins a number of archetypes in his portraits, including bus-drivers and butlers, whose outlandish appearance seems to bear no relation to their stated occupation; Condo’s cast members highlight the inadequacy of fixed labels in an age of fractured styles and compound identities. The apple and arrow that afflict The Secretary look like a William Tell act gone wrong – a potent symbol of misplaced faith, of illusion stripped away to expose an uncomfortable (and dangerous) truth. The theatre of painting has been torn down. ‘I describe what I do as psychological cubism,’ Condo has said. ‘Picasso painted a violin from four different perspectives at one moment. I do the same with psychological states’ (G. Condo, quoted in S. Jeffries, ‘George Condo: “I was delirious. Nearly died”’, The Guardian, 10 February 2014). In all her grotesquerie, the secretary’s distorted, exaggerated features exhibit an appealing and convincing character: she is wide-eyed in amazement at her dramatic revelation, and even, as all is laid bare, takes on a surprising sort of beauty.