Born in Chicago, Simon was the son of the manager of the Universal Film Exchange. Graduating from the University of Michigan and Columbia Law, he spent several years gaining experience in a variety of jobs that would be useful to him as a screen director. He was a drama coach, a speech instructor, a radio exec, a theatre director, and finally a talent scout for Warner Brothers. He then got a job directing screen tests as Universal, which led to directing features in 1937.
Most of Simon’s early work at Universal consists of forgotten B pictures, but he got his foot in the door at MGM by directing the slapstick sequences in the Marx Brothers’ The Big Store (1941) and from there he went on to helm many well-remembered pictures, including Dulcy (1940) with Ann Sothern; the Red Skelton comedies Whistling in the Dark (1941), Whistling in Dixie (1942), Whistling in Brooklyn (1943), A Southern Yankee (1948), and The Fuller Bush Man (1948); the Abbott and Costello vehicles Rio Rita (1942) and Abbott and Costello in Hollywood (1945); and the all-star Song of the Open Road (1944) featuring Jane Powell, Bonita Granville, W.C. Fields, Edgar Bergen and Charlie McCarthy, the Condos Brothers, et al. Towards the latter half of the decade he transitioned from director to producer. These later movies include the Lucille Ball comedies Miss Grant Takes Richmond (1949) and The Fuller Brush Girl (1950) and Jack Carson’s The Good Humor Man (1950). His last picture was the screwball comedy classic Born Yesterday (1950) with Judy Holiday, Broderick Crawford and William Holden, written by Garson Kanin, directed by George Cukor. A picture like this boded well for Simon’s future, but he died suddenly of a massive heart attack at age 41, robbing fans of decades of undoubted but now theoretical classics.
Actress Aline McMahon was Simon’s cousin; her mother Jennie Mac appeared as an extra in a few of Simon’s films.
For more on classic film comedy see my book Chain of Fools: Silent Comedy and Its Legacies from Nickelodeons to Youtube.