The Sin of Harold Diddlebock (1947)

In the golden year of 1923, Harold Diddlebock, a seemingly aimless college football hero, finds his life path unexpectedly illuminated by a single game-winning moment on the field. This fleeting glory catches the eye of E.J. Waggleberry, a titan of the advertising world, who offers Harold an entry-level accounting position at his firm, promising a prosperous future. Filled with naive optimism, Harold envisions himself swiftly ascending the corporate ladder, but destiny has a different plan. Flash forward twenty-two years to 1945, and Harold, rather than sitting atop a corporate empire, still finds himself ensnared in the confines of his entry-level job. His lack of progress leads to his dismissal by the ever-demanding Waggleberry, a blow made all the more crushing by the fact that it severs his daily interactions with Miss Otis, a charming graphic artist at the firm. Harold's unrequited love for Miss Otis, and her six predecessors, has been a constant, unfulfilled dream of his life. Undeterred by his professional downfall, Harold departs from Waggleberry's firm with close to $3,000 in savings, attracting the attention of Wormy, a desperate gambler down on his luck. Wormy coaxes Harold into his first intoxicating sip of alcohol, sparking a whirlwind of hazy memories and eccentric adventures that land Harold back in his bed at his sister Flora's home. With his money vanished, his suit replaced by a flamboyant ensemble, and his memory blurred, Harold must confront the bizarre aftermath of his drunken escapade. As Harold pieces together fragments of his wild journey, he discovers a peculiar purchase - a lion. This unusual "asset", along with an outlandish suit, are the only remnants of his drinking and gambling spree. With no clear recollection of his antics and no way to unload his new exotic pet, Harold is forced to tap into the advertising savvy he absorbed during his stagnant twenty-two years at Waggleberry's. His mission: to navigate this surreal mess, salvaging what he can from his shattered dreams and possibly, find a way to win the heart of his beloved Miss Otis.

The Sin of Harold Diddlebock is a comedy movie featuring Harold Lloyd.

The Sin of Harold Diddlebock is currently streaming for free (ad-supported) on Plex and Plex Player and it's also available on Classix.

It is also possible to buy The Sin of Harold Diddlebock on Amazon Video.