Grandma's Boy (1922)
Before he was climbing skyscrapers, Harold Lloyd was finding his voice. Grandma's Boy is the film where he perfected the earnest, bespectacled "Glass Character" that would define his career. He plays a timid man who, terrified of a town rival and a menacing
vagrant, can't work up the courage to win his sweetheart. His grandmother saves the day by giving him a "magic" charm that belonged to his civil war ancestor, instantly filling him with courage. The twist, of course, is that the charm is a phony—the handle of her umbrella—and the strength was in him all along. This blend of gags with genuine character development was a game-changer for comedy films, which until then had largely relied on pure slapstick. It was a massive success, but its historical importance is often overshadowed by the more iconic thrill-comedies that soon followed.
For Heaven's Sake (1926)
It’s hard to imagine a film that grossed nearly $2.6 million in the 1920s becoming 'overlooked,' but that’s the fate that befell For Heaven’s Sake. In this manic comedy, Lloyd plays a clueless millionaire who accidentally burns down a coffee stand owned by a downtown mission. He falls for the minister's daughter and, through a series of misunderstandings, finds himself trying to wrangle a gang of rowdy drunks he accidentally invited to his own wedding. The final sequence, featuring Lloyd commandeering a double-decker bus full of his new, inebriated friends, is a masterclass in controlled chaos. While it was one of the highest-grossing films of the entire silent era, it gets less critical attention today than films like The Freshman or Safety Last!, perhaps because its plot is more straightforwardly frantic than character-driven.
The Cat's-Paw (1934)
After a brief hiatus, Lloyd returned to the screen with a film that was a deliberate and shocking departure from his brand. The Cat's-Paw is a strange and wonderful political satire, a talkie that relies on dialogue and dark themes rather than daredevil gags. Lloyd plays Ezekiel Cobb, the naive son of missionaries raised in China, who is brought back to America and duped into running for mayor by a corrupt political machine. To everyone's surprise, he wins and proceeds to clean up the town with a bizarre brand of ancient Chinese wisdom and intimidation. Audiences weren't ready for such a dark, dialogue-heavy film from their stunt-loving hero, and it was Lloyd's first-ever box office failure. Today, however, it is viewed as a courageous and fascinating experiment that showed the incredible breadth of his talent.
The Milky Way (1936)
Arguably Lloyd's most successful and critically acclaimed sound film, The Milky Way is a top-tier screwball comedy that has been largely forgotten by modern audiences. Lloyd plays Burleigh Sullivan, a timid milkman who, in a fluke, appears to knock out the middleweight boxing champion. A shady promoter, played by Adolphe Menjou, decides to build him up as a title contender through a series of fixed fights. Directed by the legendary Leo McCarey, the film is a perfect blend of Lloyd's physical comedy and the rapid-fire dialogue that defined 1930s comedies. While a hit at the time, Lloyd's legacy is so intertwined with his silent-era daredevilry that his excellent talkies, including this gem, have unfairly faded into the background.
The Sin of Harold Diddlebock (1947)
What do you get when you cross one of Hollywood's greatest silent comedians with one of its most iconoclastic writer-directors? You get this fascinating, bizarre, and ultimately unsuccessful film, also known as Mad Wednesday. Lloyd reprises his role from the 1925 classic The Freshman, opening with the same triumphant football game footage. Flash forward 20 years, and Harold is a lowly bookkeeper who is unceremoniously fired. After taking his first-ever alcoholic drink, he goes on a wild spree, which results in him buying a bankrupt circus, complete with a lion. Directed by the brilliant Preston Sturges, the film was a chaotic production that was taken away from Sturges and re-edited by producer Howard Hughes. It flopped twice, marking the end of Lloyd's starring career. It remains a must-see for film fans, a strange and ambitious capstone to a legendary run.
