Born in Chicago, Simon earned bachelor's and master's degrees at the University of Michigan, and later attended Columbia Law School.

Screen Test and a few Universal feature assignments earned him an invitation from MGM to direct.

He became a comedy specialist, supervising many of the slapstick sequences in the Marx Brothers' The Big Store.

He directed Red Skelton's first starring feature, 1941's Whistling in the Dark, and in 1948 worked on two more Skelton vehicles, MGM's A Southern Yankee (replacing the scheduled director Edward Sedgwick) and Columbia Pictures' The Fuller Brush Man.

Simon also directed Wallace Beery in Bad Bascomb (1946), and a Glenn Ford western, Lust for Gold (1949).