The Sin of Harold Diddlebock

In 1923, Tate College freshman Harold Diddlebock joins the football team and scores the winning touchdown, instantly making a name for himself on campus. The moment fuels his belief that he could rise to prominence through talent and leadership. It marks the first spark in his long, uncertain ascent into the world of ideas and opportunity.

Shortly after his football success, J.E. Waggleberry, a pompous advertising tycoon, offers Harold a job at his agency. Harold hopes to become an 'ideas man,' but Waggleberry assigns him to a lowly bookkeeping position instead. The mismatch plants early seeds of dissatisfaction and ambition.

In 1945, Harold is let go by Waggleberry for being too old and not an 'ideas-man.' He receives an 18-karat Swiss watch and a severance check for $2,946.12, the remnants of his company investment plan.

Harold bids farewell to Miss Otis, a young woman who works at an artist's desk, and gives her the paid-for engagement ring he had planned to place on her finger for marrying one of her six older sisters. He leaves with his life savings still in his pocket.

Harold is taken to a bar where he reveals he has never had a drink. The bartender crafts a potent cocktail called 'The Diddlebock,' whose effects trigger a dramatic personality shift and a newfound impulse to reinvent himself.

In the ensuing days, Harold undergoes a rapid makeover—haircut, manicures, and a gaudy plaid suit. He overhears Wormy with his bookie Max and impulsively bets $1,000 on Emmaline, a long-shot horse that wins and makes Harold suddenly rich, sparking a spree of spending.

Days later Harold wakes up at his sister Flora's house, hungover in garish attire and a ten-gallon hat. He discovers he now owns a horse-drawn cab and has an English driver named Thomas, along with a bankrupt circus purchased with his winnings.

Harold and Wormy visit the circus-loving banker Lynn Sargent, who declines to bid because he’s trying to unload his own bankrupt circus. Seeing a tide of bankers willing to consider the circus, Harold crafts a plan to generate interest and secure investment for ownership.

To sway the bankers, Harold, Wormy, and Jackie the lion stage a chaotic show, using a Thermos to slip them drinks and lower inhibitions. Their stunt backfires and they are arrested and jailed.

Miss Otis posts Harold's bail the next day, bringing publicity to the circus and drawing bankers back into the bidding. Ringling Brothers ultimately outbids them all, reshaping Harold's prospects.

Days later, Harold awakens in the horse-drawn cab with Miss Otis and learns he has sold the circus for $175,000. He becomes an executive at Waggleberry's advertising agency and is married to Miss Otis, who reassures him with a loving kiss.

With Miss Otis by his side, Harold steps into a leadership role at Waggleberry's agency, turning his dreams of being an 'ideas man' into a tangible reality and discovering personal happiness in his marriage.