1943 - 1952

1943: Departing from Chicago, Chamberlain embarks on a cross-country journey with the aim of a movie career in Hollywood. Shortly after crossing the Arizona/California border, however, he is arrested for evading payment of a restaurant bill. After being released, his journey is rerouted to Phoenix, where he enlists in the US Navy.

1947: Following his discharge from the navy in Chamberlain enrolls in studies focused on hairdressing and makeup artistry at the Sid Simon School in Chicago made possible by the GI Bill.

1948: Chamberlain enters into marriage with jazz singer Virginia Wooten, although they later divorce. Wooten is quoted as saying, "I married a hairdresser, not a goddamn artist."

1949-51: Post-divorce Chamberlain proceeds to receive lessons from artist and illustrator Lucretia Malcher. Subsequently, he takes a significant step by enrolling at The School of the Art Institute of Chicago to further his artistic education.

1952: Following a disagreement with his professor regarding his interpretation of Indian columns that incorporated nude bodies, Chamberlain departs from the Art Institute. The disagreement and ultimate low grade coined the phrase “it’s all in the fit,” born from the sexual nature of the columns, eventually becoming slogan for his own work.