The Simpsons: 10 Funniest Homer And Bart Moments, Ranked

When Homer isn’t strangling Bart or reprimanding him for something bad he’s done, the two of them get into some very wacky adventures. There are a number of ways in which Homer and Bart are different (for one, Bart seems to be smarter than Homer, despite his bad grades and much younger age), but there are also plenty of ways they’re alike.

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Bart even says, “D’oh!” whenever he’s annoyed, just like his father. Bart might refuse to call Homer “Dad,” instead electing for his given name, but they’ve had some hilarious moments together. Here are the 10 Funniest Homer And Bart Moments, Ranked.

10 Homer and Bart steal sugar from Hans Moleman’s truck

Out of Homer Simpson’s many insane schemes, stealing a bunch of sugar from a crashed truck to sell door-to-door has to be one of the most outlandish. He and Bart are driving along and happen to notice the truck at the side of the road, driven by Hans Moleman.

Homer tells Moleman that he’ll watch the truck for him while he goes to get some help. Moleman says, “If only this sugar were as sweet as you, sir,” but Homer just wants to steal all the sugar. It has broken glass and gravel in it, and no one wants to buy their sugar from a door-to-door salesman.

9 Bart whips Homer on the ass with their court-ordered tether

In one of the many episodes where Homer and Bart get into trouble with the law, a new no-nonsense judge orders the two to be tethered together until they can learn to love each other.

They later do learn to get along and bond as they go to Bart’s school together and then do the night shift at the nuclear plant every night, but at first, they can’t get over their differences. Early on, Homer starts strangling Bart – as he is known to do – and Bart responds by taking the slack of their tether and whipping Homer on the ass with it.

8 Homer tells Bart everything he knows about women

In the episode “Lisa the Beauty Queen,” when Marge and Lisa are out getting their hair done, Homer tells Bart that women love to be complimented. So, when they come back in, Homer and Bart compliment them on their new hairdos and get promised “a special dinner.”

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Bart is enthralled that his dad was able to impart onto him such useful wisdom, so he asks him, “Dad, do you know anything else about women?” and Homer bluntly says, “Nope, that’s it.” Still, Bart uses this information in a diner to get an extra big ice cream sundae from the waitress.

7 Homer warns Bart about the Boogeyman

Marge becomes addicted to gambling when it is legalized in Springfield in the episode “$pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling),” leaving Homer to take care of the house and the kids on his own on most nights. On one of those nights, Lisa comes into Homer’s bedroom and tells him that she thinks she saw the Boogeyman in her room.

Instead of calming her down and telling her there’s no such thing as the Boogeyman, he freaks out. He runs into Bart’s room, wakes him up, and says, “Bart, I don’t want to alarm you, but there may be a Boogeyman or Boogeymen in the house.”

6 Homer gets Bart and his fellow Junior Campers stranded at sea

In the episode “Boy-Scoutz ‘n the Hood,” Bart accidentally joins the Boy Scouts (sorry, Junior Campers) while he’s on a Squishee bender. Ned Flanders is the scout leader and he invites Homer to come along on their retreat into the woods with Ernest Borgnine as a parent volunteer and they end up getting stranded at sea.

Homer eats all the food rations and also punctures their raft, so things are looking futile. However, they’re saved when Homer sniffs out a nearby Krusty Burger located on an oil rig. He bursts through the doors and demands to have all the burgers they’ve got in stock.

5 Homer and Bart endure painful leprosy treatments for a free vacation

In the episode “Little Big Mom,” Lisa is left at home alone with Bart and Homer while Marge recovers from an injury. When she reaches her breaking point, she paints them with green spots to make them think they have leprosy. Ned Flanders offers them some hospitality and eventually sends them to a leper colony in Hawaii.

There, they realize that they don’t really have leprosy, but since they enjoy being on the beach in Hawaii and see their stint at the leper colony as a “free vacation,” they put up with painful treatments for a disease they don’t have.

4 Young Bart flushes Homer’s car keys down the toilet

In the flashback episodes to when Bart and Lisa were younger, we see that Bart was even more of a menace as a little kid – especially when he was still an only child, before Lisa came along. He’d swing around on the clothesline hanging between two apartment buildings and jump off the TV onto a sleeping Homer’s stomach.

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In one case, he took Homer’s wallet and his car keys and flushed them both down the toilet, much to a struggling Homer’s dismay. Compared to his younger self, the 10-year-old Bart we see today is a warm-hearted and well-behaved boy.

3 “The worst day of your life so far.”

Early on in The Simpsons Movie, Bart strips naked and skateboards across town after Homer dares him to. He ends up being chained to a signpost outside a Krusty Burger by the police, and when Homer comes to pick him up, he only brings him socks and a t-shirt, so he has to pull the t-shirt down to cover his crotch.

Bart proclaims it to be the worst day of his life, but Homer corrects him: “The worst day of your life so far.” The Simpsons Movie was a lot better than anyone expected it to be, and Matt Groening has promised a Disney-mounted sequel.

2 Bart hits Homer with a chair

This gag is so hilarious and timelessly funny that, all these years after the episode “A Milhouse Divided” first aired, it has become a popular meme online. It’s from the episode where Milhouse’s parents split up, and following the separation, Milhouse’s mom starts dating a guy who calls himself “your average workaday stuntman.”

He shows off his skills as a stuntman by getting Luane to break a chair over his back. Bart decides to test whether or not his own father figure can do this by sneaking into the bathroom and breaking a chair over Homer’s back while he’s in the bathtub.

1 Homer jumps Springfield Gorge on Bart’s skateboard (almost)

Homer Simpson falling down Springfield Gorge

In many ways, season 2’s “Bart the Daredevil” was the first truly great episode of The Simpsons. Every episode up until that point had been about grounded, real family situations, but “Bart the Daredevil” took that one step further by surrounding the relatable family antics with absurdist sight gags.

The episode’s final sight gag remains an all-time classic in the Simpsons fan base. It starts with an emotional moment, as Homer tries to implore Bart not to put himself in danger, and then leads to surreal fun as Homer accidentally ends up jumping Springfield Gorge on Bart’s skateboard (well, almost).

NEXT: The Simpsons' 10 Saddest Moments, Ranked

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