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Challenging the Bully

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Bully characters in fiction often seem to use very similar tactics with similar motivations. Beyond just beating up or tormenting their victim, they like humiliating them more than anything — and what a better way than to publicly beat them at a challenge or watch them back down as a coward?
As such, this plot occurs when a bully and their victim — who is often the protagonist — face off in a challenge. Sometimes it's a traditional fight, which often results in the victim getting a Boxing Lesson. Other times it's an actual contest in a field the bully believes the protagonist will have no talent in. Sometimes someone will set up the challenge for the protagonist in the assumption that they'll win, or the protagonist themselves will make the declaration, but there must be an actual challenge offered for this trope to occur. If the protagonist is the one to make the declaration, they're usually fighting for someone other than themselves. Or, the bully themselves will challenge the protagonist.
These challenges are almost always public (even if it wasn't meant to be, a la Spontaneous Crowd Formation). They can occur as the climax of the story, but it's not a requirement, as they can also happen at any other point.
Results may vary. In most cases the protagonist wins, either thanks to their hard work preparing and the bully's overconfidence, the Beware the Nice Ones factor, or because the bully was Bullying a Dragon. In some cases, this will lead to Defeat Means Friendship in works that avert Status Quo Is God. However, it most often doesn't lead to anything, and the bully will remain their usual selves come next episode. Sometimes, however, the bully ends up the victor regardless, often with a Curb-Stomp Battle.
Compare Not Afraid of You Anymore; May overlap with Took a Level in Badass. This challenge may involve a Game of Chicken.
Please note that for an example to fit this trope, a challenge of some form must be present or implicit. A character standing up to their bully without a challenge being made is not this trope.
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Harry Potter and the Philosopher's Stone:
Draco Malfoy challenges Harry to a duel at night in, but this is a Subverted Trope because Draco doesn't actually show up and just wanted to get Harry into trouble.
Malfoy steals a Rembrall from Neville, a frequent target of his bullying, and mocks him for injuring himself. Harry gets tired of this and rises on his broomstick, challenging Malfoy to a contest of flying skills. Harry is able to retrieve the Rembrall through a tricky broomstick maneuver, defending Neville's honor and coming out on top.
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The Simpsons episode "Bart the General" has Bart defending Lisa from school bully Nelson Muntz (making his debut), and gets beat up for his efforts. This leads to a final confrontation between the two, which becomes a pastiche of WWII movies.
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In The Amazing Spider-Man (Lee & Ditko), while Peter was still in high school, he gets forced by a teacher to challenge his bully, Flash Thompson, to a boxing match. This, of course, puts Peter in the situation of how to resolve things without giving away that he's Spider-Man. Eventually, he just pops Flash in the jaw hard enough to leave Flash dazed and unable to keep fighting, and tells the crowd that obviously Flash is throwing the fight, since wimpy Peter Parker couldn't possibly hit hard enough to knock him out in one blow. The crowd is quick to jump on this as evidence that Flash must be Spider-Man, throwing the fight so as to avoid revealing his superpowers.
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Sky High (2005): Thanks to his newfound powers, Will's friends decide he'd be able to defeat the two bullies, Speed and Lash, in a game of Save The Citizen. Though he spends the conversation insisting he has no interest in competing with them, the challenge is made anyway, with the stakes being a year without bullying or his friend's head being dunked in the toilet every day.
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Three O'Clock High: Double subverted. Most of the film's plot follows Jerry Mitchell's increasingly insane attempts to escape the fight challenge that school bully Buddy Rydell has given him, but on the third act Buddy pisses Jerry off by calling him a coward and thus Jerry accepts Buddy's challenge for real.
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The premise of the Ninja Sex Party song "Cool Patrol" is Danny Sexbang teaching a high school boy getting picked on how to deal with bullies. The training consists of learning a silly dance, but gives the kid enough confidence to approach the bullies with an implicit challenge... before he's promptly beaten up and possibly killed.
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In "After School Special", the season 4 episode of Supernatural, we see in a flashback that, in a desire to blend in and be normal, Sam will ignore bullies that pick on him personally, but woe to anyone who picks on people Sam considers to be a friend or under his protection. When bully Dirk decides to beat up Sam's new friend Barry, even kicking him when he's already down. Sam tells Dirk to leave Barry alone, but Dirk cockily challenges the diminutive Sam to a fight. Sam proceeds to lay a curb stomp beatdown on the bully, despite Dirk being easily twice Sam's size. He also crowns the bully Dirk the Jerk, a nickname that would follow the bully the rest of the way through school.
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In Yu-Gi-Oh!, this is the M.O. of Yugi Muto — or, more accurately, his Superpowered Evil Side. Because of Yami Yugi's shadow magic, this typically ends with the bully coming down with a bad case of Mind Rape. This also happens in the anime, but with more card games and less mental punishment for Yugi's opponents.
Played for Laughs in Season 0 of Yu-Gi-Oh! The Abridged Series when Yugi finds a bully has beaten his friends, decides enough is enough and challenges him to a Children's Card Game. The bully then informs Yugi that Duel Monsters won't be introduced until the next season. More beatings ensue, until Yugi's Superpowered Evil Side manifests to challenge the bully to a Shadow Game.
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Homicide: Life on the Street: In "Full Court Press", a bullied teenager confronts his bully after he sexually assaults him with a gun in the hopes of scaring him. When the bully continues to taunt him, the teenager snapped and shot him dead.
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One of the Nickelodeon Clickamajigs involves challenging and beating up a stereotypical school bully.
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In My Huntsman Academia, Izuku stands up to Cardin Winchester during his eighth week at Beacon, challenging him to a fight in sparring class in front of everyone else. Cardin, being the Smug Snake he is, agrees. But Izuku has been actively grinding as many levels of badass as he could since they met in his first few weeks at Beacon, including developing One For All: Full Cowl. Cardin's complacency proves to be his undoing when Izuku utterly curb-stomps him without taking any damage, destroying Cardin's reputation and forcing him to stop bullying others.
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In Persona 4 SILVER BLUE, Labrys does this to Ai Ebihara and Hanako Ohtani when she first meets them, although unlike most examples of this trope, she doesn’t fully realize that this is what she’s doing until later. It’s also a case of Adaptational Karma, since neither of them really had to face any consequences for their actions or attitudes in canon.
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Luz Noceda from The Owl House is prone to this, especially in defense of her (few) friends and often in a somewhat ill-considered manner:
In "Covention", Amity's treatment of King prompts Luz to challenge her to a Witches Duel. Amity is at the top of the class in her track while Luz has at this point figured out to, with preparation, create a ball of light.
"Wing It Like Witches" sees Luz demand Boscha face her in grudgby match over the latter's ongoing harassment of Willow, Gus, and herself. Boscha is the captain of the school's top-ranked grudgby team, while Luz is not quite sure how to even play.
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In Weak Hero, once it becomes clear that the class bully Phillip is full of hot air, Teddy challenges him to a fight in the middle of the classroom. As expected, when Teddy throws the first punch, Phillip flinches away and proves that he doesn't have anything beyond his bravado.
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Doraemon: In one chapter, Doraemon has to go back to the 22nd century because his duty has been "fulfilled" (i.e making Nobita happy), but he's reluctant because he comes to care about Nobita too much. Nobita tries to prove that he doesn't need Doraemon anymore, one of the methods being challenging the local bully, Giant. While Nobita is badly beaten, he keeps coming after Giant, who ended up getting scared of him because he just won't back down. This at least convices Doraemon to go back "home". This particular plotline was used as the final act of Stand by Me Doraemon.
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Phineas and Ferb: "Raging Bully" introduces the character of Buford, who is shown as a stereotypical bully when he challenges Phineas to a fight after the latter spills ice-cream on him. The fight turns out to be a thumb war treated like a boxing match, and Buford almost wins until Phineas gets ice cream on his own shirt thanks to Perry and Doofenshmirtz. Buford calls off the fight, seeing as he and Phineas are even, and they become friends.
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A History of Violence: Jack spends much of the movie being tormented by Jerk Jock Bobby and his sidekicks. After learning the truth about his father, Jack decides he's had enough and takes Bobby's next provocation—a command to "make him laugh"—as an excuse to beat the ever-loving crap out of him.
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In All Japan Women's Pro-Wrestling, the feud between the Crush Gals (Lioness Asuka and Chigusa Nagayo) and Dump Matsumoto's Atrocious Alliance in the mid-80s is a famous example. The Atrocious Alliance ran rampant through AJW, and the Crush Gals were the underdog Faces standing up to them. The heat generated from the audience was comparable to what Hulk Hogan was getting at the same time in the US.
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Drake & Josh: The pilot episode features Josh getting challenged to fight a bully who believes he was dating his girlfriend (when, in reality, it was Drake). Josh spends the episode learning karate and eventually gets really good at it... but still loses the fight after one single blow.
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Ned's Declassified School Survival Guide: In "Guide to Your Body", Ned gets roped into a weightlifting contest against Loomer thanks to an attempt by Coach Dirga to defend him. Though he and everyone else believes he'll fail, Dirga teaches him the proper technique to lifting weights, and he ends up defeating Loomer in front of the entire school.
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In Song of the Lioness Ralon is a petty bully, constantly picking on main character Alanna secure in the knowledge that she (though he thinks she's a boy) can't report him without losing honor. So, for the next few months she spends her nights training in hand-to-hand combat and then challenges him in the practice yard in front of everyone. And totally kicks his ass.
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In the Peanuts special "He's a Bully, Charlie Brown", Charlie Brown finds himself standing up to a marble-stealing bully named Joe after spending days learning to play. They have a public match and Charlie Brown talks him into playing a game for all the marbles, which Joe arrogantly accepts, then loses.
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Skippy Dies combines this with Cock Fight. Skippy and Carl are both rivals for Lori's affection, but Skippy is a quiet nerd who is frequently bullied, while Carl is a psycho who bullies younger kids and sometimes pushes Skippy around. After being repeatedly threatened, Skippy challenges Carl to a fight. Surprisingly, Skippy is able to land a punch on Carl and "win" the fight, by visualizing attacks from his favorite video game.
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Attempted in the The Boondocks episode "Shinin'" where Riley tries to take on local bully Butch Magnus after he stole a piece of jewelry from him. Unfortunately Riley doesn't actually know how to fight while Butch Magnus is several times his size and is capable of beating up adults. Later on, Riley comes back with a grown man for backup only for Butch Magnus to easily beat the guy up. However he gives Riley his jewelry back, stating that he had it appraised and learned it was worthless. Riley walks away content while his "friend" is crumpled in pain.
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The fight was reimagined in the first arc of Ultimate Spider-Man. Peter orders Flash to stay away from Mary Jane, and this led to an after school fight, but Peter simply tries to elude his attacks. At one point, he manages to stop one of his punches with his hand, and that broke Flash's hand. He spent many later issues with the hand bandaged, and had to be removed from the basketball team.
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The Book of Lies (2004): After Fergus begins fighting one of the disabled orphans, Marcel challenges Fergus to a steeplechase.
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A Christmas Story: Ralphie ends up challenging (and thrashing!) the local bully Farkus after Farkus hits him in the face with snowball. Ralphie was already having a bad day, and this was the final straw.
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Ultimate Daredevil & Elektra: When Elektra saw Trey abusing a female student with his gang, she forced him to return her folder. First she told him, then she took him down and humiliated him.
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In one Peanuts strip, Linus complains about always having to watch whatever Lucy wants to watch on tv. Lucy then threatens to slug him, but instead of backing down, or taking the hit like usual, Linus just walks over to the tv, changes the channel, and then looks Lucy directly in the eye and says, "You don't frighten me one bit." Linus gets to watch his show while Lucy just stands there and cries.
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Spider-Man:
In The Amazing Spider-Man (Lee & Ditko), while Peter was still in high school, he gets forced by a teacher to challenge his bully, Flash Thompson, to a boxing match. This, of course, puts Peter in the situation of how to resolve things without giving away that he's Spider-Man. Eventually, he just pops Flash in the jaw hard enough to leave Flash dazed and unable to keep fighting, and tells the crowd that obviously Flash is throwing the fight, since wimpy Peter Parker couldn't possibly hit hard enough to knock him out in one blow. The crowd is quick to jump on this as evidence that Flash must be Spider-Man, throwing the fight so as to avoid revealing his superpowers.
Subverted in one of the earliest issues. Peter has enough of Flash's bullying, and grabs him to start a fight. Then he remembers that he has superpowers, and may seriously harm or even kill Flash if they fight (and reveal his identity), so he let him go.
The fight was reimagined in the first arc of Ultimate Spider-Man. Peter orders Flash to stay away from Mary Jane, and this led to an after school fight, but Peter simply tries to elude his attacks. At one point, he manages to stop one of his punches with his hand, and that broke Flash's hand. He spent many later issues with the hand bandaged, and had to be removed from the basketball team.
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In the Tiny Toon Adventures episode, "Hero Hamton", Hamton accidentally hits Montana Max with his locker door. When he tries to apologize, Monty threatens to beat him up, and Plucky makes the situation worse by telling Monty that Hamton could easily beat him in a fight. Monty then challenges Hamton to a fight after school, with Plucky charging people admission to see the fight. Much of the episode involves Hamton first trying to get out of the battle before eventually accepting it and being trained by his friends for the inevitable showdown.
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My Little Pony: Friendship Is Magic: In "The Cutie Mark Chronicles", it's revealed that Rainbow Dash and Fluttershy were both bullied by three colts who first appeared in "Sonic Rainboom". Rainbow Dash stood up for Fluttershy and in the process ended up in a public race against the three bullies, fighting "for Fluttershy's honor".
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South Park: In "Breast Cancer Show Ever", Wendy Testaburger, after getting fed up with Eric Cartman mocking breast cancer, challenges him to a fight after school. Cartman does everything he can to weasel out of the fight without openly apologizing, from bribery to telling his mother, but eventually cedes. Cue a devastating No-Holds-Barred Beatdown from Wendy that leaves Cartman lying in a pool of his own blood.
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In The Mask: The Animated Series episode "Split Personality", a high school bully, Chet Bozzack, who tormented Stanley Ipkiss, to the point that he was expelled from the school, gets employed in the same bank where Stanley works. He initially seems to have mellowed out, with occasional moments of Jerkassery here and there. Then the mask gets split in half and then Chet finds one half and puts it on, releasing his repressed personality, which is a big bully. He ends up challenging Stanley (who still has the other half of the mask) for a fight in their old high school campus, as an act of revenge for getting him expelled. Unfortunately for Chet, while Stanley's normal self is still afraid of his former school bully, his repressed half (i.e The Mask) isn't and he is far more experienced with the powers of the mask. The resultant fight is almost one sided (though Chet does get his occasional moments), before things take a murderous turn and even Chet is horrified by his masked half's actions and manages to fight his inner demons, meanwhile, Stanley's masked half reveals he was only pretending to be helpless for fun. The episode ends with Chet realising he still needs help and deciding to start a new life in a new city.
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One game on It's My Life (PBS) involves writing a story where a kid confronts a bully.
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The following is a list of statements referring to the current page from other pages.

 Challenging the Bully
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Competition Index
 Challenging the Bully
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The Bully
 Doraemon / int_52092250
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Challenging the Bully
 Retro Chill (Fanfic) / int_52092250
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Challenging the Bully
 Racing Stripes / int_52092250
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Challenging the Bully
 Sky High (2005) / int_52092250
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Challenging the Bully
 Harry Potter and the Philosopher's Stone / int_52092250
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Challenging the Bully
 La Fuerza Series / int_52092250
type
Challenging the Bully
 Skippy Dies / int_52092250
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Challenging the Bully
 Doraemon (Manga) / int_52092250
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Challenging the Bully
 Rokudou's Bad Girls (Manga) / int_52092250
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Challenging the Bully
 Ninja Sex Party (Music) / int_52092250
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Challenging the Bully
 Drake & Josh / int_52092250
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Challenging the Bully
 Ned's Declassified School Survival Guide / int_52092250
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Challenging the Bully
 Nickelodeon Clickamajigs (Video Game) / int_52092250
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Challenging the Bully
 School Bus Graveyard (Webcomic) / int_52092250
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Challenging the Bully
 Star Impact (Webcomic) / int_52092250
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Challenging the Bully
 Weak Hero (Webcomic) / int_52092250
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Challenging the Bully
 It's My Life (PBS) (Website) / int_52092250
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Challenging the Bully
 The Mask / int_52092250
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Challenging the Bully
 All Japan Women's Pro-Wrestling (Wrestling) / int_52092250
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Challenging the Bully