While starring in Dick van Dyke Show (1961), Van Dyke called up Stan Laurel to ask for permission to do a Laurel & Hardy bit in an episode. Laurel told him that neither he nor Hardy's heirs owned the rights to the characters. Van Dyke and Reiner were horrified that Laurel didn't even own the rights to his own face, and this picture is the result.
In his autobiography, Carl Reiner said he intended this as a vehicle for Dick Van Dyke who had, on the set of their TV show, often expressed the wish that he had been working at the same time as comedy legends such as his hero Stan Laurel.
Writers Carl Reiner and Aaron Ruben wrote the story loosely based on the career of Buster Keaton - primarily the decline of his fortunes as tastes changed in Hollywood and his alcoholism. Some elements of the lives of Harold Lloyd and Mickey Rooney were also incorporated into this film.
Mickey Rooney wore a special prosthetic in his right eye to play Cockeye. The character was originally supposed to be cross-eyed, but on the first day of shooting the actor claimed he was physically unable to do this. Director Carl Reiner confirmed this by placing his finger on the tip of Rooney's nose and telling him to look at it, without result. Reiner later said about Rooney, "This man could do everything in show business - sing, dance, act - but he couldn't cross his eyes!"
Billy Bright appears in a comic parody called "Dr. Jerk and Mr. Hyde." Many years earlier, Stan Laurel made a short Dr. Pyckle and Mr. Pride (1925) in which Mr. Pride is a devilish practical joker. It was one of Laurel's best reviewed solo films, before his teaming with Oliver Hardy.