"Cross-eyed but sharp of mind" is how an encyclopedia compiled in A.D. 900s characterized Menander, the leading playwright of Greek New Comedy. Although he was only moderately successful during his lifetime, the government of Athens commissioned a portrait statue of Menander at his death in about 290 B.C. Kephisodotos and Timarchos, leading sculptors of the time, created this statue, now lost, which stood in the Theater of Dionysos in Athens.
Menander's plays, and in turn his portrait, experienced a resurgence of popularity with the Romans. More than sixty surviving Roman portraits depict a clean-shaven, lean-faced man with high cheekbones and a tall, rectangular forehead. For a long time scholars were not sure whom these portraits represented. Then this bust, conveniently labeled with an inscription on the base identifying the subject as Menander, solved the scholarly dilemma. All these Roman portraits of Menander appear to derive from a common model, and stylistic features indicate that this model was the head of the statue made by Kephisodotos and Timarchos.