Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (2024)

Part of what madeSeinfeldso ceaselessly entertaining was not only its four main characters but its eclectic cast of recurring side characters. Newman, Frank Costanza, David Puddy, are some examples of side characters whose episodes were always a special treat for die-hard fans of the show.

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One of these beloved side characters is Jerry's Uncle Leo, played by Len Lesser.Leo is sneaky, paranoid, passive-aggressive, and oftentimes oblivious to what's going on around him, though at times, like Jerry himself, he reluctantly goes out of his way to help others. His episodes are uniquely funny in that they offer glimpses into Jerry's family life. Here are Leo's 10 funniest moments onSeinfeld,ranked.

The Edible Foliage Tour

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (1)

Uncle Leo's first-ever appearance onSeinfeldis in Season Two's "The Pony Remark." At a family dinner, Leo grabs Jerry's ear and raves to him about his son Jeffrey's job as a tour guide in Central Park. He brags about the "Edible Foliage Tour" that Jeffrey has created, and also insinuates that Jeffrey leans on him for support when he has a problem with the "big shots" at the Parks Department.

Jeffrey never actually appears onscreen, but his career at the Parks Department is a continuing source of pride for Leo throughout the series.

"You Gotta Go, So Go"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (2)

In addition to being overbearing, Leocan also be very passive-aggressive. When he runs into Jerry and George while they're hailing a cab to an important meeting with NBC executives, he launches into a story about how he used to get free pajamas from his friend Danny Palmer. When Jerry apologizes and says he doesn't have time to talk to him, Leo responds by telling him to go ahead, and that "nobody's got a gun to his head."

Jerry latergets a phone call from his parents, who accuse him of being rude to his uncle, which means that Leo obviously called them to complain about Jerry's behavior, despite his supposed understanding at the time of the encounter.

"Believe Me, I Don't Owe Your Mother Fifty Dollars"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (3)

Leo is also a sneak. When Jerry's Nana calls both Jerry and Leo for help opening a bottle of ketchup, they both meet at her apartment. Nana, a bit out of it, asks Leo if he ever gave $50 to his sister, Jerry's mother, from his father's winnings at the race track. She mentions how Leo was given $100 and told to give $50 of it to Helen.

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Jerry is confused by this story, but Leo assures him there is no reason to be suspicious. "Believe me," he says, "I don't owe your mother fifty dollars." Jerry isn't so convinced.

Leo Learns Of Jerry's "Wedding"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (4)

In "The Wife," Jerry is offered a lifetime discount at his local dry cleaner's, and his girlfriend pretends to be his wife so she can take advantage of the discount as well. When Leo runs into them at the dry cleaner's, he is surprised and confused tohear from the dry cleanerthat Jerry has been married.

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Jerry is forced to lie to him and confirm that he has in fact been married, and Leo is of course offended that he wasn't invited to the wedding.

"If Anybody Asks You Where You Got It, You Don't Know"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (5)

In Season Six's "The Pledge Drive," Jerry cashes some of Nana's old checks that she gave him years ago as a gift, which causes problems for Nana, seeing asshe no longer has the checking account from which the checks were written.

Leo learns of this and thinks Jerry is in dire straits financially. He finds him backstage at the pledge drive and tries stuffing some money in Jerry's pocket. Even while performing an act of kindness, his paranoia surfaces, telling Jerry, "If anybody asks you where you got it, you don't know!"

The Watch Transaction

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (6)

When Jerry throws out the watch his father, Morty, gave him because it doesn't work, Leo finds it in the trash can and takes it. When Jerry, Leo, and Morty are at dinner, Morty starts inquiring about the watch, noticing that Leo's is suspiciously similar to the one he gave Jerry.

Sensing his father is onto him, Jerry corners Leo in the bathroom and offers him $200 for the watch. Leo insists that money isn't the issue, but that he loves the watch and doesn't want to part with it. Of course, when Jerry ups his offer to $350, Leo instantly agrees. Of course, it's all for naught, because Morty walks in and catches them in the act, forcing Jerry to confess that he threw out the watch.

"I'm An Old Man, I'm Confused!"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (7)

In Season Nine's "The Bookstore," Leo is revealed to be a petty thief with "prior convictions." He steals books from Bentham's bookstore, thinking that if he's ever caught, he can claim he's just a confused old man who thought he paid for them.

When Jerry catches him in the act, he alerts security, thinking they'll only scare him into putting the books back. Instead, they "swarm" Leo and place him under arrest. Leo tries giving them the "confused old man" line, but it doesn't work as he'd hoped.

"They Don't Just Overcook A Hamburger"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (8)

In Season Seven's "The Shower Head," Leo moves in with his new girlfriend, which creates a problem for Jerry, as his parents are able to live in Leo's vacant apartment. Wanting them to move back to Florida, Jerry meets Leo for lunch to try and convince him to break up with his girlfriend so he can move back into his place and evict Jerry's parents.

When Leo's hamburger comes back medium instead of medium-rare, he insists that the cook must have deliberately overcooked his burger, accusing the chef of antisemitism. Jerry attempts to get the conversation back on track, continuing, "The point I was making before Goebbels made your hamburger here, is this..."

"Now You're Just Being Difficult"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (9)

In "The Package," Leo's eyebrows and mustache are burned off when his stove explodes. He goes to the doctor, where Elaine meets him to pose as his nurse, hoping to score a remedy for her rash, which she can't get treated because her doctor has blacklisted her as a "difficult" patient. She flees in a panic when she becomes paranoid that Leo's doctor is onto her, but before she goes, she draws Leo a new pair of eyebrows.

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Unfortunately, her eyebrows came out angry looking, and the doctor becomes threatened by Leo's "demeanor" upon returning to the room.

"Stop The Show!"

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (10)

Later in "The Pledge Drive," after Leo shows up backstage to give Jerry money, Jerry's Nana calls into the show to make a donation to PBS. When Kramer announces this on the air, Leo rushes onto the set in a frenzied panic, insisting that Nana cannot afford to make such a donation, embarrassing Jerry and derailing the event.

"She can't do that, she's on a very fixed income!" He screams. He then rushes the camera, arms in the air, and yells,"Stop the show!"

NEXT: 10 Best Frank Costanza Episodes Ranked, According To IMDb

Seinfeld: The 10 Most Hilarious Uncle Leo Scenes, Ranked (2024)
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