Lloyd was never to star in another film, turning instead to production, and releasing compilation films featuring his earlier silent film work.
In 1945, twenty-three years after scoring the winning touchdown for his Tate College football team (as told in The Freshman), mild-mannered Harold Diddlebock (Harold Lloyd), who has been stuck in a dull, dead-end book-keeping job for years, is let go by his pompous boss, advertising tycoon J.E. Waggleberry (Raymond Walburn). He is given an 18 karat Swiss watch that is 'properly inscribed "with gratitude and love and kisses for 20 years devoted services"' and a check for $2,946.12, the remains of his company investment plan. He bids farewell to Miss Otis (Frances Ramsden), who works at an artist's desk down the aisle, giving her the paid for engagement ring that he had, having planned to marry each of her six older sisters (Hortense, Irma, Harriet, Margie, Claire, and Rosemary) when they had worked there before her. He wanders out, aimlessly through the streets, his life's savings in his trouser pocket.
While looking through the newspaper want ads for another job, Harold is approached by Wormy (Jimmy Conlin), a local con artist, petty gambler, and racetrack lout, who asks Harold for some money so he can place a bet. Seeing the large amount of cash that Harold has, and hoping to get him drunk enough to acquire some of the cash, Wormy takes the depressed and unemployed Harold downstairs to the local bar for a drink. When Harold tells the bartender, Jake (Edgar Kennedy), that he has never had a drink in his life, the barkeep creates a potent cocktail he calls "The Diddlebock", one sip of which is enough to release Harold from all his inhibitions, setting him off on a day-and-a-half binge of spending, gambling, and carousing.
A day or two later, Harold wakes up on the sofa inside the house of his widowed sister Flora (Margaret Hamilton). He finds that he has a hangover, but he also has a garish new wardrobe, a ten-gallon cowboy hat, a horse-drawn hansom cab complete with driver, and ownership of a bankrupt circus.
Trying to sell the circus, Harold and Wormy visit circus-loving Wall Street banker Lynn Sargent (Rudy Vallee). When he turns them down, the rest of the town's bankers follow suit. To get past the bank guards, Harold brings along Jackie the Lion, who incites panic. Carrying a filled Thermos, Wormy gives shot drinks of the potent "Diddlebock" cocktail to each of the bankers they visit so their inhibitions will fade and convince them to put in bids for ownership of the circus. Things take a turn for the worse when the lion gets loose, in which Harold, Wormy, and the lion end up on the ledge of a skyscraper, but narrowly avoid plunging to certain death.
According to Harold's plan, the three (Harold, Wormy, and Jackie the Lion) are arrested and thrown in jail. Miss Otis bails them out, and they find that the publicity has attracted a mob of bankers who want to buy the circus – but Ringling Brothers outbids them. Harold celebrates with another "Diddlebock", and again has another relapse. In the final scene, Harold wakes up another day or two later in the horse-drawn cab with Miss Otis where he learns that he received $175,000.00 for the circus, he is now an executive at Waggleberry's advertising agency, and that he and Miss Otis are married.
Cast and character notes:The Sin of Harold Diddlebock was Lloyd's last original film.
Although the film explicitly connects the character of Harold Diddlebock to that in The Freshman, in the earlier film his surname is Lamb.
This movie was the only credited feature film appearance of Frances Ramsden (1920—2000), whose role is important enough that she could have received second billing.
After Howard Hughes re-edited the film, Rudy Vallee's part was almost entirely cut out, and he did not receive screen credit on the re-released film, Mad Wednesday, nor did Georgia Caine. Also, Lloyd's billing was moved from above the title to below, provoking Lloyd to file a $750,000 lawsuit in 1953 against RKO and California Pictures, claiming breach of contract.
The supporting cast of Harold Diddlebock is largely made up of charter members of Preston Sturges' unofficial "stock company" of character actors, including Al Bridge, Georgia Caine, Jimmy Conlin, Robert Dudley, Robert Greig, Arthur Hoyt, J. Farrell MacDonald, Torben Meyer, Charles R. Moore, Frank Moran, Jack Norton, Franklin Pangborn, Victor Potel, Dewey Robinson, Harry Rosenthal, Julius Tannen and Max Wagner.
After writer-director Preston Sturges left Paramount Pictures in 1944, he and millionaire Howard Hughes formed California Pictures, and in July of that year it was reported that Sturges had tempted one of his idols, Harold Lloyd, out of retirement to become a producer-director at the new studio, with his first project to be "The Sin of Hilda Diddlebock", a story written by Sturges about a girl's adventures in Hollywood, and their second project a film called "The Wizard of Whispering Falls" (Lloyd had not appeared on film since 1938's Professor Beware). Even after Lloyd became the lead character, he was promised by Sturges that he could direct part of the film, but this never happened. Although the project began as a labor of love between Sturges and Lloyd, the two had a falling out over creative differences, which affected the quality of the finished film.
The Sin of Harold Diddlebock went into production on 12 September 1945. California Pictures was a new company and didn't have adequate facilities to make the film, so Sturges attempted to buy Sherman Studios. When he failed, production on The Sin of Harold Diddlebock was located at Goldwyn Studios, with additional shooting – including the window ledge scene which recalled a well-known similar scene from Lloyd's Safety Last (1923) – at Paramount Studios. Some location shooting (for the hansom cab scenes) took place on Riverside Drive in Los Angeles. By the time that filming wrapped on 29 January 1946, the film was $600,000 over budget.
The film premiered in Miami, Florida on 8 February 1947, and went into general release on 4 April. Despite Sturges' later claim that the film "got the best reviews I ever received," the notices were mixed and commented on the unevenness of the comedy, perhaps the result of the falling out between Sturges and Lloyd. Sturges claimed that producer Howard Hughes used the reviews as an excuse to re-make the film.
In May, it was reported that Hughes was running a contest for his employees to find a shorter name for the film, with the winner to get $250; the next month, after it had only played in three cities, the film was pulled from circulation and its name changed to Mad Wednesday, because of concerns that the word "sin" in the title would hold back the film's box office from the "family trade". It was intended to return the film to distribution as soon as October, and a special effects crew was sent to San Francisco to film process shots to be used in the film's re-editing.
In the event, because of Hughes' re-editing of the film and re-shooting of some scenes – Sturges said that Hughes "[left] out all the parts I considered the best in the picture, and adding to its end a talking horse" – the film was not ready for re-release until 1950. United Artists backed out of their distribution deal with Hughes, so after Hughes bought RKO, he used his new studio to release the film, now cut from 89 to 76 minutes, on 28 October 1950. The total cost of the film was estimated to be $1,712,959.
Both versions of the film, as originally released and as altered by Hughes, still exist. The shorter version plays better for audiences, while the original is richer in its comic invention and characterizations.
In 1951, Harold Lloyd received a Golden Globe nomination as "Best Motion Picture Actor - Musical/Comedy", and the film was nominated for Grand Prize at the Cannes Film Festival that same year.