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Bully and Wimp Pairing

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In fiction with child heroes, it's common to have a bully and his most frequent victim as supporting characters, typically as a Foil or Mirror Character. While the bully might feature as a villain, in stories where they are on the main characters' side, they are frequently paired up with the wimp as a sort of Big Guy, Little Guy double act. If the wimp isn't just weak, but also portrayed as smart, then can also cross over into Brains and Brawn, making use of the Brains Versus Brawn contrast.
Usually Played for Laughs: either the wimp is unhappy at being paired with the intimidating bully, the bully is unhappy that he's not allowed to beat on the wimp while they're supposed to be working together, or embarrassed to be seen with him, or the two get along surprisingly well considering their normal relationship. If the school works to make these characters get along, it becomes School Forced Us Together.
This can also be caused by a Bully Turned Buddy scenario, if the bully isn't entirely over their bullying ways and, this time, the bullying can be a form of Tough Love to make the Wimp stronger. If we get to see them as adults, they usually evolve into Sensitive Guy and Manly Man or even more often Vitriolic Best Buds, especially if neither of them will allow a third party to show the other up.
Almost Always Male, female-on-female examples are almost non-existent since this is based on physical strength and the visual of a larger and stronger character paired with a smaller and leaner character of the same sex, rather than psychology or relational aggression. However, you can find a female bully and a male victim as a subversion and often in a comedic tone. The other way around (i.e. male bully/female victim) is very rare and almost always Played for Drama, comedic examples being completely exceptional.
In a completely different kind of fiction, Seme/Uke pairings may feature this.
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Horimiya has the female lead Hori and her Childhood Friend/former bullying victim Sengoku. The two can be seen hanging out when they aren't with their respective love interests.
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The Simpsons:
Whenever a group of kids includes Nelson and Martin, it seems the two end up paired together. "Team Discovery Channel!" Nelson is usually rather unhappy about this.
Every once in a while this dynamic is played when Nelson is involved. A prominent example is the episode "The Haw-Hawed Couple", when he and Bart (who takes on the "wimp" role here) become friends.
Also Bart Simpson and Milhouse, to a lesser extent (while Milhouse is certainly a wimp, Bart is more a troublemaker than an actual bully like Nelson). Bart treats Milhouse more like a sidekick than a victim, and a flashback episode showed they became friends when Milhouse was nice to Bart when the latter was suicidally depressed after attending kindergarten.
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Biff Tannen and George McFly in the original timeline of Back to the Future. George is really unhappy about it, but he's been stuck with doing Biff's errands all his life because he never had the courage to tell him off.
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Batman Forever: Two-Face and the Riddler are another villainous variation.
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In Disney's version of Beauty and the Beast, Gaston and Lefou, while adults and villains, have this kind of dynamic, with Gaston being the Jerk Jock bully and Lefou his wimpy underdog sidekick.
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In a more serious example, Neon Genesis Evangelion gives us the second and third Eva pilots Shinji Ikari and Asuka Langley Soryu, who are often forced to work together and live in close quarters; Asuka being the bully and Shinji being the wimp. Of course, to their misfortune, this becomes a quite literal pairing.
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Total Drama:
Duncan spends most of his time torturing Harold, but due to the nature of the show, they also find themselves working together often. When they get past their differences, they actually make quite a good team, being the clutch to win several challenges across Island and Action.
Jo and Cameron aligned with each other for a decent chunk of Revenge of the Island.
The Spin-Off Total Drama Presents: The Ridonculous Race has Kelly and Taylor (i.e. team Mother and Daughter) with Taylor as the bully who constantly belittles and walks all over her mother with Kelly not doing a thing to stop her until the episode where they go home.
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Paranorman gives us the titular Norman, and local bully Alvin. Their relationship gets less antagonistic once the Zombie Apocalypse starts.
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In Bully, the game starts out with Gary and Petey playing this role, although it's not a perfect fit since Gary is more into mind games and emotional manipulation than physical bullying. When Jimmy takes Gary's place, the trope works better as Petey and Jimmy work as a Brains and Brawn team, although of course how much Jimmy acts like a typical bully is purely up to you.
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Phineas and Ferb: Buford (bully) and Baljeet (nerd) regularly get paired together. Over the course of the show their relationship slowly begins to evolve into Vitriolic Best Buds, and Baljeet's exasperation with this trope is well-illustrated in the episode "Bully Bromance Breakup."
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The Super Mario Bros. could arguably been seen as this; with the bold, heroic Mario as the "bully" and the shy, cowardly Luigi as the "wimp".
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In My Hero Academia, protagonist Izuku Midoriya continues to hang around his childhood bully, Katsuki Bakugo, because he admires Bakugo's drive to be the best. Bakugo is extremely aggressive and hot-headed around him in return, calling him "Deku" because of Midoriya's Quirklessness and seeming inability to accomplish things on his own. However, Bakugo doesn't allow anyone else to call him "Kacchan" the way Midoriya does (although, Kaminari does so anyway) and the pair mellows out into Bully Turned Buddy as the story develops, but they still retain this dynamic whenever they talk to each other. Until Bakugo undergoes a tremendous amount of Character Development and apologises for his behaviour that is. He stops calling him Deku and starts using his first name but makes it clear that he still sees him and the others as his rivals.
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Zed and Sweetchuck in the Police Academy film series. Zed is an unstable gang leader while Sweetchuck is a timid flower shop owner, and the two are at odds, but once they join the force, they gradually become less antagonistic to each other.
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Dan Vs..: The title character (bully) and his only friend Chris (wimp) can be considered a grown-up version of this pairing.
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Ultimate Spider-Man: Peter runs away from home, but where can he go? With Mary Jane? No, her parents would call Ben and May. So he goes with Kong, the school bully. After all, they are basketball teammates now.
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Scut Farkus and Grover Dill in A Christmas Story are a villainous variation.
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The Witch of Knightcharm: Lily's gang of magic bullies includes Brynne, a weak and apparently hapless witch who sucks up to the other witches constantly but still gets pushed around and is made to take care of menial tasks for them. The protagonist Emily theorizes that Brynne can't leave the gang because they're providing her with supplies she needs (like glasses after she breaks her own during orientation for their new Wizarding School) and so she's forced to put up with their cruelty.
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Living together in The Trouble With You Lilian are Madge (bully) and Lilian (wimp). As Lilian is Madge's paying lodger, Madge treats her poorly, knowing that as she has nowhere else to stay all she can do is take the abuse.
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7 Seeds has Natsu, a shy girl who stopped going to school because she was constantly bullied, and Semimaru, a guy who used to be bullied himself and decided to fight back and who repeatedly teases Natsu. It grows to Loving Bully territory, where he mostly teases her cause he's embarrassed or because he tries to toughen her up.
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In Neither a Bird nor a Plane, it's Deku!, Izuku still has this relationship with Katsuki Bakugou. The twist in this story is that Izuku is Kryptonian and is far more powerful than his bully, who wants him to go to U.A. so they can settle their score.
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Susie from Deltarune is such an overwhelming bully that she forms this relationship with just about everyone she meets. When first introduced, she threatens to bite Kris's face off. Kris, meanwhile, is a different variation of "Wimp;" rather than a simpering nerd, they're a withdrawn, moody, lonely kid who's the town's only human resident, all of which make them a pretty ripe target for bullying. Fortunately after the first chapter Susie becomes a Bully Turned Buddy and she and Kris count each other as close friends. She still plays the dynamic straight by throwing her weight around and making sure everybody knows she's the toughest member of her crew. Especially toward the polite, fluffy, and sweet-tempered Ralsei.
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South Park has Eric Cartman and Butters Stotch. OK, Cartman and any other kid, but moreso Butters, as Kenny hasn't been as much of a Butt-Monkey for quite a while.
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Harry and Marv in the Home Alone films, sort of. Harry is short but brave, while Marv is tall but cowardly.
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There is actually a lot of these parings in Hey Arnold!:
Arnold Shortman (wimp) with both Helga G. Pataki and Harold (bully). Helga only bullies Arnold in a way to hide her true feelings for him but because of this constant bullying, Arnold himself finds it hard to be around her. Despite this, Arnold and Helga do get along and will help each other when one is in trouble. And with Herald is a classic example of the big tough guy picking on the smaller wimpy guy. However, Herald Took a Level in Kindness and doesn't really bully Arnold anymore even becoming one of his more closer friends.
Interesting case with Arnold and Torvald (bully). At first, Torvald would bully Arnold and other kids for their lunch money but after Arnold helps him with his math, Torvald becomes much more friendlier with Arnold. He still bullies other kids, though.
Ironically, Helga becomes this whenever Patty is around. Helga is by no means a weak person but Patty dwarfs her in size, strength, and brutality. Whenever Helga makes an insulting comment about Patty, Patty isn't afraid to take her to a broom closet and beat her up. In a different episode, Patty was going to beat up Helga badly but was convinced not to by Arnold with the both of them agreeing he's a nice guy. They're not "friends" per say but they're a lot better now than they started off.
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Doug: The title character (wimp) with Roger (bully). Despite the two of then having their differences and Roger taking every opportunity to bully/humiliate Doug, the two of them are good friends especially shown in the last episode of the Nickelodeon series "Doug Graduates." And there were other times where Roger does look out for Doug.
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Long Exposure has Mitch and Jonas, the two main characters who are forced together in an environmental science project together. Played with in that while Jonas doesn't want to be anywhere near his tormentor, Mitch secretly has a raging crush on Jonas. Add the fact their research for the project leads to them developing super powers and their dynamic gets even more complicated.
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On Succession, Tom and Greg are Those Two Guys operating on the periphery of the uber-rich Roy clan. Their middle-class origins and outsider status saddle them with each other's company, and even though Tom (the bully) runs the younger, meeker Greg (the wimp) roughshod, the two are often a united front due to their shared low position in the Roy hierarchy.
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Duo Tropes
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The Bully
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The Jerk Index
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Youngsters
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