It was based on a play starring Dressler, Tillie's Nightmare. In the film Chaplin plays a sleazy city slicker who stays the night at a farm. When he sees that the farmer has a large bankroll, he romances the farmer's daughter, the large, homely, not terribly bright Tillie (Dressler), and gets her to steal her father's bankroll and run away with him. Once they reach the big city he gets her drunk, steals the wad of cash, and rejoins his sexy girlfriend (Normand). An abandoned Tillie takes a waitressing job, but it turns out that the simple farm girl has a very, very rich uncle. And that uncle is promptly reported dead, lost in the mountains while he was on a vacation, leaving Tillie the heir to a vast fortune. This gets the city slicker interested in Tillie again.
Tillie's Punctured Romance spawned three film sequels, all of which starred Dressler. At 74 minutes long, it was not just the first feature produced by Mack Sennett's Keystone Studios, it was the first feature-length comedy made by anyone anywhere. Comedies in fact would remain almost all short films for several years to come. After Charlie Chaplin left Keystone and assumed control of his own career, which happened not long after this film, he would take six more years before making his own first feature, The Kid. As for this film, Tillie's Punctured Romance is Chaplin's feature film debut and the last time he appeared in a film directed by someone else, with the exception of a couple of As Himself cameos.
This film provides examples of:
- Bottomless Magazines: After catching Charlie and Mabel canoodling, Tillie whips out a gun. She fires approximately 20 shots.
- Camp Gay: The city slicker is bothered by an effeminate man at the dance. The character is very camp indeed, which was necessary to get the idea across in a dialogue-free film.
- Can't Hold His Liquor: Tillie makes a spectacle of herself after having one drink at a restaurant. This helps the city slicker to steal her bankroll.
- Celebrity Paradox: When Charlie and Mabel go into the theater, one of the advertisements is for Keystone film Double Crossed, which starred Chester Conklin and Mack Swain, two actors in this movie.
- Country Mouse: Tillie is such a bumpkin that she can't even manage crossing the street, and nearly gets run over by several streetcars.
- Curtain Call: The original film had an out-of-character epilog where Dressler, Chaplin, and Normand appear on a stage and bow for the camera. This is not always included in modern home-video versions.
- Down on the Farm: Where the movie starts. Poor ignorant Tillie is vulnerable to the advances of the city slicker.
- Early Installment Weirdness: It's odd to see Chaplin not only out of his Tramp costume, but playing the villain.
- Farmer's Daughter: Part of the joke, of course, is that a great big woman like Dressler is playing such a part, but otherwise the trope is played straight. Tillie knows nothing of the wider world and falls for the city slicker's con.
- Gold Digger: Once the city slicker finds out via a newspaper article that Tillie has become suddenly wealthy, he swiftly marries her.
- Good Hair, Evil Hair: The city slicker's sleazy pencil mustache is a clear sign of villainy (and an interesting contrast to The Tramp and his toothbrush mustache).
- Hammerspace: Where Tillie gets the gun that she starts shooting at the climax. Unless she just carried a gun with her while dancing with her husband at a party.
- HeelFace Turn: After Charlie is dragged away by the cops, Mabel breaks down sobbing, and she and Tillie hug as the film ends.
- Imperial Stormtrooper Marksmanship Academy: Tillie tries to kill Charlie and Mabel, but she is a very bad shot.
- Lemming Cops: Naturally, the Keystone Kops appear, and a ridiculous madcap chase ends the movie, after Tillie's not-really-dead uncle shows up and demands that everyone who trashed his mansion be arrested. This one ends at the Santa Monica Pier, with the "Water Police" joining the scene so the film could include Lemming Cops on a boat.
- Literal Ass-Kicking: Many, many times, starting in the first scene when Tillie's father kicks his own daughter in the butt to get her to start working.
- No Name Given: For the characters played by Chaplin and Normand.
- Nouveau Riche: Tillie and the city slicker make asses of themselves when Tillie comes into money, abusing the servants, trashing the place, starting a gunfight.
- Pie in the Face: A variation, as an enraged Tillie starts flinging custard at people.
- Re-Cut: Different versions can be found in different places; the 2003 restoration increased the running time to 82 minutes. Some versions include a brief prologue where Dressler appears in front of a stage curtain, before two dissolves transition to her in costume on the farm, as well as a brief epilogue where Dressler, Chaplin, and Normand appear in front of the curtain and take a bow.
- Show Within a Show: Charlie and Mabel go to see a Keystone Studios film called A Thief's Fate, which makes them feel guilty when it turns out to be a lampshading of their theft of Tillie's money. (A Thief's Fate was not a real Keystone movie.)