The Sin of Harold Diddlebock is a 1947 comedy film written and directed by Preston Sturges, starring the silent film comic icon Harold Lloyd, and featuring a supporting cast including female protagonist Frances Ramsden, Jimmy Conlin, Raymond Walburn, Rudy Vallee, Arline Judge, Edgar Kennedy, Franklin Pangborn, J. Farrell MacDonald, Robert Dudley, Robert Greig, Lionel Stander and Jackie the Lion. The film’s story is a continuation of The Freshman, one of Lloyd’s most successful movies.

The Sin of Harold Diddlebock was Sturges’ first project after leaving Paramount Pictures, where he had made his most popular films, but the film was not successful in its initial release. It was quickly pulled from distribution by producer Howard Hughes who took almost four years to re-shoot some scenes and re-edit the film, finally re-releasing it in 1950 as Mad Wednesday – but the reception by the general public was no better the second time around.

Lloyd was never to star in another film, turning instead to production, and releasing compilation films featuring his earlier silent film work.

Plot
In 1923, Tate College freshman Harold Diddlebock (Harold Lloyd) is brought into his college’s football team where he scores the winning touchdown (as told in the silent feature film The Freshman). The mild-mannered Harold is quickly offered a job by the pompous advertising tycoon J.E. Waggleberry (Raymond Walburn). After completing his college studies a few months later, Harold meets with Mr. Waggleberry at his advertising office for the job offer. Although Harold dreams of becoming an “ideas man,” Waggleberry assigns him to a lowly position in the bookkeeping department.

Jumping forward 22 years later to the year 1945, the now middle-aged Harold, who has been stuck in his dull, dead-end book-keeping job, is let go by Waggleberry for old age and not being an ideas-man. 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), a young woman 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 tout, 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 to a 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. The effects of the alcohol causes Harold to yowl uncontrollably. Gazing at himself in the bar mirror, Harold suddenly declares himself a loser and races out to remake himself. Soon Harold is getting his hair cut and his nails manicured at a local tailor shop and salon, and is trying on a gaudy plaid suit supplied by tailor Formfit Franklin (Franklin Pangborn). In the midst of his transformation, Harold overhears Wormy talking with his bookie Max (Lionel Stander), and impulsively bets $1,000 of his money on a 15-to-one long shot horse named Emmaline. To everyone’s surprise, Emmaline wins, and the now-rich Harold, with $15,000 in his pockets, begins to celebrate all around town on a day-and-a-half binge of spending, gambling, and carousing.

A few days later, Harold wakes up on the sofa inside the house of his widowed sister Flora (Margaret Hamilton) where she chastises him for his wild, irresponsible behavior. He finds that he has a hangover, but he also has a garish new wardrobe and a ten-gallon cowboy hat. Unable to remember much about his drunken binge, particularly about what he did on Wednesday which is a total blank, Harold wanders outside to return the plaid suit where he is surprised to learn that he now owns a hansom horse-drawn cab complete with an English driver named Thomas (Robert Greig). A worried Wormy then rushes up and informs Harold that, with winnings from a second bet, Harold also bought a bankrupt circus. After a meeting with the animal handlers and circus freaks, Harold first seeks help from the Kitt-Poo Home for Cats to feed the circus’ starving lions and tigers. Seeing no future with the ownership of the circus, Harold then gets the idea to sell the circus to a Wall Street banker.

Harold and Wormy visit the circus-loving Wall Street banker Lynn Sargent (Rudy Vallee) to ask him to purchase their circus, but he turns them down because he is trying to unload his own bankrupt circus. When the rest of the town’s bankers follow suit, Harold comes up with an idea. To get past the bank guards, Harold dresses up in his plaid suit and brings along Jackie, a tame circus 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 the following day, and they find that the publicity has attracted a mob of bankers at the jail 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 for the sale of the circus, he is now an executive at Waggleberry’s advertising agency, and that he and Miss Otis are married. Reassuring Harold that she truly loves him, Miss Otis gives him a big kiss, and Harold finally remembers what he was doing all day on Wednesday. The final shot shows Wormy tagging along with them by riding on the back bumper of the cab.

Cast
Harold Lloyd as Harold Diddlebock
Jimmy Conlin as Wormy
Raymond Walburn as E.J. Waggleberry
Frances Ramsden as Miss Otis
Rudy Vallee as Lynn Sargent
Edgar Kennedy as Jake, the bartender
Arline Judge as Manicurist
Franklin Pangborn as Formfit Franklin
Lionel Stander as Max
Margaret Hamilton as Flora
Jack Norton as James R. Smoke
Robert Dudley as Robert McDuffy
Arthur Hoyt as J.P. Blackstone
Julius Tannen as Nearsighted Banker
Al Bridge as Wild Bill Hickock
Robert Greig as Algernon McNiff
Georgia Caine as Bearded lady
Torben Meyer as Barber with mustache
Victor Potel as Prof. Potelle