The high school hustler effortlessly outfoxes authority figures — particularly those who are irrational and hidebound. He's just packed full of brainpower, connections, chutzpah and luck.
He can arrange a Chain of Deals and make it work for everybody. He can pull off a Bavarian Fire Drill without getting his bluff called. Often he's out for himself, but frequently willing to help those in need.
The High School Hustler may use some friendly Dumb Muscle to deal with problems his brains can't beat. Other times he's the Karmic Trickster, using his brains to dish out poetic vengeance to bullies and protecting the weak. But he's also the guy running the betting pool and selling term papers.
He is not a straightforward young hero. He lusts for payment in return for his good deeds. Popularity might be his deepest motivation. He won't demand payment from those who can't pay though, or run out on his friends. He just likes to take the easy and stylish road to success. In general he is a good guy.
The High School Hustler is the positive adolescent version of the Mouthy Kid. Usually he's regarded as a good kid by almost all adults save those whose authority he directly challenges — and he can maintain that camouflage even under fire.
The character type is predominantly male. He is the ideological nemesis of Dean Bitterman. If he grows up and joins a Five-Man Band he'll either be The Leader (a type 1: mastermind) or if the The Leader is The Hero he'll be The Lancer to foil his purity. Other possibilities are The Face or The Smart Guy who comes up with the sneaky plans. If the lead male in a Six Student Clique isn't The Ace, he'll usually be this...or some combination of the two. When he graduates high school, he may become a Frat Bro upon entering college, but any fraternity he joins will be usually see him preside over a bunch of dorky outcasts as their charismatically rebellious trouble-making leader rather than the bullying Jerk Jocks who make up the other fraternities.
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Nabiki Tendo from Ranma ½, though more of a Barnum than not. She rarely (if ever) cares about the consequences other people have to face for her actions, though.
Suzumiya Haruhi: One of Haruhi Suzumiya's many strengths is the ability to get away with practically anything, up to and including extortion, indecent exposure, commandeering an entire room, and press-ganging members, and make the SOS Brigade end up in a better situation by the end of the episode. Her peculiar brand of conscientious amorality tends to help with this. The fact that she is possibly God probably helps a lot more. However, this trope is probably played straight. Her "recruiting" of Asahina in Disappearance (where she can't cheat) is a good example: She flings the door open, claims to be from the Student Council Intellignece Agency...and drags an upperclassman out. No problem.
Tamaki from Ouran High School Host Club is charming and managed to gather the members of the club despite being the last thing any of them needed (or so they thought). In the last two episodes of the anime, Tamaki falsely believes that he has really mucked up everyone's lives instead of helping them and it pushes him to make a rash decision. He's wrong, of course; even though he is constantly pulling the others along in eccentric plans and gimmicks, his carefree look on life is the right medicine for everyone.
Negiri from Futaba-kun Change!. Originally nothing more than a Captain Ersatz of the more famous Nabiki Tendo (above) she quickly became a more sympathetic, friendly and professional example of this trope.
Hiruma of Eyeshield 21 is an example of what happens when the High School Hustler becomes a Drill Sergeant Nasty football player. At heart, Hiruma is a good guy who loves football and cares about his teammates. That said, he's not afraid to blackmail people to get what he wants and god help the people who piss him off or get in his way. His ability to manipulate situations to benefit himself scares even authority figures.
In the novel, a precocious middleschool hustler!Orihara Izaya of Durarara!! was the bookie of the school's betting pool for baseball. It didn't run so smoothly when a better who had betted using stolen money from his father's wallet threatens Izaya with a knife. Shinra steps in to receive the blow. In return for telling people that it was actually Izaya who did it, Izaya vows to make the stabber regret his move for his entire life. Knowing Izaya, it probably works. All too well.
In the beginning of Catch Me If You Can, Frank uses his cleverness to teach a French class for two weeks, and then tells a girl getting out of class with a parental note that her paper is incorrectly folded. She resists his implication at first, then surreptitiously takes his advice.
Creepy example: Roger Corman's Rock 'n' Roll High School features Clint Howard (at 20, an unfortunate mix of Dawson Casting and Younger than They Look) as the enterprising Eaglebauer, who resides in a Bigger on the Inside office that is accessed through a stall door in the boys' bathroom (leading to massive lines for that one stall) which includes a receptionist with her own klaxons (a girl approaching inspires a red alert). Eaglebauer's ability to sell students' needs borders on the satanic, with many references to selling touchdowns in football games to the male protagonist and a plot revolving around characters paying to become sexually involved with their desired love interests.
Back to the Future: Marty McFly is a variant of this trope. Note that he is less of a trickster but no less lucky and helpful. The earlier drafts did make him a little more of this type of character, though.
Van Wilder is what happens when this character goes to college. And then stays there for almost a decade.
P. G. Wodehouse's Psmith started as this, and arguably maintained it into adulthood, becoming a master of the Indy Ploy. He notably prevented his best friend getting expelled from school for something he didn't do by first going through astonishing contortions to hide the evidence pointing to him (a shoe stained with red paint), then, when it looked like that would fail, merrily confessing to the crime — even though he hadn't done it either.
Harry Potter: Fred and George Weasley, particularly in their later years at school.
Zack Morris of Saved by the Bell was so good at pulling off ridiculous schemes that he almost qualifies as The Great Gazoo. He is also revealed to have some issues from his often-absentee businessman father.
The sequel series tried to rebottle lightning with a host of similar characters, with little success.
Veronica Mars is a more organized version of this trope, with her father's backing (such as when he finds her in the principal's closet, and rather than ratting her out, says, "Yep. That's mine", referring to his coat). References Parker Lewis Can't Lose and his "step into my offices" by frequently having people at her school "ambush" her in the bathroom with "I need you to help me."
Star Trek: Deep Space Nine: Nog, a Ferengi character. In one episode, he helps Chief O'Brien find a much-needed graviton stabilizer through a series of bizarre exchanges, trading Captain Sisko's desk for an induction modulator from the USS Musashi, for a phaser emitter, which is finally traded for a graviton stabilizer.
In another episode from the first season, Nog was told to get rid of some Cardassian packaged food that had been delivered to the bar, since there were no more Cardassians on the station who would order that food. Jake Sisko and Nog sold the food to a trader who gave them self-sealing stembolts that a Bajoran farmer had ordered but had been unable to pay for.
Jake and Nog contacted the farmer to try and get money from him in exchange for the stembolts but the farmer could only pay them in land. Meanwhile, the land had become prime because the Bajoran government wanted to build something on it but didn't know who owned it. Jake and Nog approached Quark (who had mentioned he wanted the land so he could sell it at an inflated price), saying that they had something to sell him and that was the end of the episode.
Maeby in Arrested Development, who swindles her way into a job as a successful movie executive before graduating high school through a combination of right place / right time and sheer Refuge in Audacity.
Squib of 15/Love was a Jerk with a Heart of Gold and borderline Manipulative Bastard who lived to torment the school president, Harold Bates. Bates bans sugar on the premises, Squib smuggles in chocolate bars. Bates wants extra training sessions, Squib tries to get them removed, etc, etc. Unfortunately for Squib, Bates was far from stupid, and won more often then not.
Griff Hawkins on Boy Meets World takes this trope Up to Eleven, organizing pro wresting matches in the schools gymnasium in one episode.
He also got Robert Goulet to sing at his ensuing detention.
In the Community episode "Conspiracy Theories and Interior Design" Jeff is a junior call version. He seeks out "blow off classes" and failing to find one he isn't beyond making up an imaginary class to get unearned credits in a style which would make Ferris Bueller proud. But he's put to shame by "Professor Professorson"'s fake class, teacher, and entire night school... Or he would have been if any of that were true.
In "Pillows And Blankets", the narrator refers to his scheme to interfere with classes as "Ferris Buellerian".
"Rip-off" Rodney of iCarly. His wares range from concert tickets to burritos.
Sam: Okay! So you got anything else to say to the iCarly fans of the world?
Ripoff Rodney: Yeah. I've got a special this week on burritos.
[opens up his jacket to reveal a bunch of burritos]
Ripoff Rodney: Two for six bucks.
Carly: And do they contain quality meat?
Ripoff Rodney: No they do not.
In "Life Skills," a fourth-season episode of The Middle, Axl (who normally wouldn't fit this trope) manages to pull together an impressive demonstration of how to run an Italian restaurant by calling in favors from a wide group of students in less than an hour, saving his class project not only for himself but for his sister.
Split between two characters in Press Gang: Spike Thompson was the cool, in-control aspects, while Colin Matthews was the teenaged Honest John.
Radar O'Reilly of M*A*S*H fits this trope in a military setting. The initially teenaged Company Clerk was constantly making trades, notably in one episode to secure a supply of tomato juice for Col. Potter (who had forgotten he was allergic to it).
Raz of Psychonauts has elements of this in his character, although he is younger than average. The bad guy of the game is Coach Oleander, the kind of adult that any High School Hustler would be against.
Humphrey: Kevin Harnisch from O'Grady practically makes a religion out of pulling schemes.
TJ from Recess certainly qualifies, though the actual hustling aspect was given to the "Hustler Kid".
Big Gino from Hey Arnold!, who fronts an elementary school organized crime syndicate.
Jonesy of 6teen qualifies, when he's not getting caught at least.
Max Goof in Goof Troop is a perfect example of this trope, both in school and out of it. He comes up with many plans which are overwhelmingly successful, though there are a few times when his Zany Schemes either turn into Shaggy Dog Stories (with his hapless friend suffering for it) or end up putting him in serious danger because of his severe recklessness. He is fairly self-centered and ambitious but generally is a good person and will help out others.