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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.
- Paranorman gives us the titular Norman, and local bully Alvin. Their relationship gets less antagonistic once the Zombie Apocalypse starts.
Anime and Manga
- Chrona and Ragnarok from Soul Eater.
- Dumb Muscle Gian and Spoiled Brat Suneo in Doraemon could be considered this as they generally appear together.
- Kendo Team Captain Kuno and the pale outcast Gosunkugi frequently team up to defeat Ranma. Though Kuno is shown in some stories to be unpopular himself and just oblivious to it.
- 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.
- 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.
- Buchi and Taishou from Mekko Rarekko are great friends, despite Taishou being a bit of a bully towards Buchi. But later in the series he gets much better and he stops being mean to him altogether.
- 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.
- 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.
- 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. Also Bart and Milhouse, to a lesser extent (while Milhouse is certainly a wimp, Bart is more a troublemaker than an actual bully like Nelson).
- Before that, in Matt Groening's Life in Hell comic, a strip featured the 64 different types of elementary school students. Two of these were "The Bully" and "The Bully's Little Pal." A good gig, if you can get it.
- Back to The Simpsons, 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.
- Total Drama: Duncan and Harold, Duncan and Cody, Jo and Cameron.
- Phineas and Ferb: Bulford (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."
Baljeet: From this moment on, I am no longer your nerd!
- South Park has Cartman and Butters. OK, Cartman and any other kid, but moreso Butters, as Kenny hasn't been as much of a Butt Monkey for quite a while.
- Dan Vs..: The title character (bully) and his only friend Chris (wimp) can be considered a grown-up version of this pairing.