The Stooges offer to repaint their landlady's apartment in order to avoid being evicted. Landlady Mrs. MacGruder (Kitty McHugh) warns them that the "furnishings cost a pretty penny," so the Stooges destroy her place without fail. Just as they are packing a trunk to leave, Shemp receives a telegram from his Uncle Phineas Bowman (Emil Sitka) who is coming to visit. When Mrs. MacGruder hears the wealthy bachelor Uncle Phineas is worth $6 million, with Shemp his sole heir, she allows the Stooges to stay.
Later, while Shemp is preparing Upside Down Cake, pretty new neighbor Gertie Duggan (Dani Sue Nolan) comes by to borrow a cup of sugar. While making casual conversation, Shemp keeps repeating, "'Duggan', 'Duggan'...I know that name from somewhere." Gertie confirms Shemp's curiosity when she says her husband is professional strongman Rocky Duggan (Mickey Simpson), known for easily tearing thick telephone books for kicks. Within seconds, Gertie takes a fall in the boys' kitchen, leading to Shemp accidentally tearing off her skirt when trying to help her up. Realizing that all three Stooges will be beaten into submission if husband Rocky gets wind of this, they frantically hide Gertie. Just then, Uncle Phineas arrives, and all seems fine until Gertie, now resplendent in Shemp's bathrobe, makes a dash for her apartment. Rocky sees this, and comes barging into the Stooges' apartment, knocking Phineas to the floor.
Just when the towering Hercules is grinding Shemp into powder, Mrs. MacGruder shows up and demands Rocky let go of Shemp. He responds by saying, "Beat it, lady. No dame is gonna tell me what to do." Without missing a beat, MacGruder knocks Rocky to the ground with a right hook to the jaw. As Gertie comes running to her husband, she pleads, "Honey, this whole thing was a mistake." "Mistake?" he moans, and then proceeds to spit out his teeth, griping "Look at my choppers!" Mrs. MacGruder then enters the Stooges' apartment to find a weary Uncle Phineas, who turns out to be her childhood sweetheart. While Shemp is promising Rocky new teeth, since he is his uncle's sole heir, Phineas and MacGruder rekindle their romance, and decide to get married, leaving Shemp and the Stooges without an inheritance and Rocky without teeth. Incensed, the strongman chases after the Stooges once more. As they round the corner of the apartment complex, each Stooge plus Rocky races past Uncle Phineas, knocking him down. As the haymaker, Gertie runs right over the fallen uncle, and squarely kicks him in the jaw.
Semi-conscious, Phineas receives a hug from the caring MacGruder, and moans, "All I wanted was a nice, quiet visit."
- Moe Howard as Moe
- Larry Fine as Larry
- Shemp Howard as Mr. Shemp Howard
- Emil Sitka, as Phineas Bowman
- Kitty McHugh, as Mrs. MacGruder
- Dani Sue Nolan, as Mrs. Duggan
- Mickey Simpson. as Rocky Duggan
- Snub Pollard as Telegram messenger
Gents in a Jam was the last short directed by Edward Bernds, long considered the Stooges' finest director. Producer Hugh McCollum was discharged and, as a result, Bernds resigned out of loyalty to McCollum, leaving only director/short subject head Jules White to both produce and direct the Stooges' remaining Columbia comedies.
Almost overnight, the quality of the Stooge shorts declined. Production was significantly faster, with the former four-day filming schedules now tightened to two or three days. In another cost-cutting measure, White would create a "new" Stooge short by borrowing footage from old ones, setting it in a slightly different storyline, and filming a few new scenes often with the same actors in the same costumes. White was initially very subtle when recycling older footage: he would reuse only a single sequence of old film, re-edited so cleverly that it was not easy to detect. The later shorts were cheaper and the recycling more obvious, with as much as 75% of the running time consisting of old footage. White came to rely so much on older material that he could film the "new" shorts in a single day.