George Condo's "Toy Heads" series from 2012 comprises eighteen robot-like portraits, including notable figures such as Iron Man, Mike Kelley, and Picasso. These works highlight Condo's iconic reconstructed Cubist heads, reflecting his deep engagement with and reinterpretation of Cubist techniques, moving beyond mere visual representation to explore the complexities of identity and its manifestation. The series engages in a rigorous interrogation of portraiture, delving into Condo's preoccupations with the nature of subject-hood and its relationship with the painted surface. By integrating references to Picasso and Warhol, notably in works like "The Young Sailor," which pays homage to Matisse’s "The Young Sailor" (1906) and Picasso’s "The Sailor" (1943), Condo creates a dialogue with past masters while presenting his unique vision. "The Young Sailor" stands out within the series for its direct tribute to these artists, with Condo's cubist head adorned in a striped Breton shirt, a symbolic nod to the artists' iconic attire​ (Sothebys.com)​.

Condo's work is deeply influenced by his experiences in the New York art scene of the 1980s, where he emerged alongside figures like Keith Haring and Jean-Michel Basquiat. Unlike his contemporaries who might have leaned more heavily into the shock value and innuendo prevalent in art at the time, Condo charted a unique course, drawing inspiration from the vast inquiries of aesthetics and formal considerations pioneered by Old Masters like Caravaggio and Rembrandt, as well as the cubist innovations of Picasso. This blend of historical reverence with contemporary sensibility is evident in the "Toy Heads" series, where the playful and grotesque converge in a highly imaginative world, inviting viewers to reconsider the traditional boundaries of portraiture and representation. Through this series, and his broader oeuvre, Condo has coined terms like ‘artificial realism’ and ‘psychological cubism’ to describe his approach to creating caricatures, intimate portraits, and grotesque abstractions that challenge and expand the possibilities of figurative painting​ (Phillips)​.

In essence, George Condo's "Toy Heads" series is a testament to his profound engagement with the history of art and his innovative contributions to contemporary painting. By reconfiguring traditional cubist methodologies to explore the artificiality of visual representation and the complexities of identity, Condo not only pays homage to the masters but also advances the conversation on the nature of portraiture in the modern era.