The character of Benjamin Stone was based on Mel Brooks, while Alan Swann was based on Errol Flynn. Also, one of the lines Swann uses was based on something said by another actor with a drinking problem, John Barrymore.
The main character's first name, Benjamin, is the same as the last name of the director, (Richard Benjamin while his last name, Steinberg, is the same as the last name of one of the screenwriters (Norman Steinberg).
Peter O'Toole was originally hesitant about doing the film. However, in the script, the date of Swann's death was, in fact, the date of O'Toole's birthday. O'Toole phoned Richard Benjamin to find out if they did that with all of the actors they had offered the part to. The director replied that the script had not been given to anybody else, at which O'Toole agreed to do the film.
The restaurant scene has Alan Swann stealing another man's date. The man yells "Somebody stole my girl!" The song the band breaks into is "Somebody Stole My Gal" which was written by Leo Wood in 1918.
The Broadway musical version opened at the Vivian Beaumont Theatre on December 10, 1992, ran for 36 performances. Lainie Kazan recreated her role from the movie and was nominated for the 1993 Tony Award (New York City) for Supporting or Features Actress in a Musical.
Director Richard Benjamin offered Peter O'Toole the role of Alan Swann the day that O'Toole was nominated for an Academy Award for The Stunt Man. When executive producer Mel Brooks found out about the timing of the offer, he yelled at Benjamin "Well that was brilliant. Do you have any idea how much money that cost us?"
Tim Curry was nominated for the 1993 Tony Award (New York City) for Supporting or Features Actor in a Musical for "My Favorite Year" as the larger than life actor Alan Swann.
In later years, writer Dennis Palumbo quit the film business to become a psychotherapist, specializing in dealing with difficult actors, directors and other creative types.
The part of Lil, the wardrobe lady, was played by Selma Diamond. She herself was a writer for Your Show of Shows', the television program on which the film was based.