Jean-Michel Basquiat’s Self-Portrait as a Heel (Part Two) will be going under the hammer on 15th November at Sotheby’s New York. At eight-feet high and estimated between $40-60m - if the piece sells within this estimate - it will be amongst the most expensive Basquiat works ever sold.

Indeed, Basquiat’s auction record of $110m was achieved for ‘Untitled’, a skull painting created in 1982, the same year as Self-Portrait as a Heel (Part Two).

Basquiat painted Self-Portrait as a Heel (Part Two) during an extended stay in Los Angeles, a critical turning point in his life when he debuted in his first West Coast exhibition at Larry Gagosian’s Gallery.

Self-Portrait as a Heel (Part Two) is understood to be autobiographical and about Basquiat’s experience in Los Angeles. During his time here, Basquiat produced three works incorporating the word “heel”. The term can be used to describe the “bad guy” in colloquial language. This indicated that Basquiat is vilifying himself in this self-portrait, perhaps as a form of commentary on the racism present in America at this time. Or, perhaps, he is presenting himself as an “anti-hero” of the art world.

Often his paintings depict flesh coming away and bones being exposed. In this work, his body is twisted unnaturally, his hands are outstretched and his mask-like face grimaces in an almost skeletal manner.

Basquiat’s interest in anatomy can be said to date back to a pivotal moment in his childhood when he broke his arm after being hit by a car. While he was in hospital, his mother gave him a copy of Gray’s Anatomy. This medical anthology would go on to inform his art.