The high school hustler effortlessly outfoxes authority figures — particularly those who are irrational and hidebound. They're just packed full of brainpower, connections, chutzpah, and luck.
They can arrange a Chain of Deals and make it work for everybody. They can pull off a Bavarian Fire Drill without getting their bluff called. Often they're out for themselves, but they're frequently willing to help those in need.
The High School Hustler may use some friendly Dumb Muscle to deal with problems their brains can't beat. Other times they're the Karmic Trickster, using their brains to dish out poetic vengeance to bullies and protecting the weak. But they're also the kid running the betting pool and discreetly selling term papers, old exams and six-packs of beer.
They are not a straightforward young hero. They lust for payment in return for their good deeds. Popularity might be their deepest motivation. They won't demand payment from those who can't pay though, or run out on their friends. They just like to take the easy and stylish road to success. In general they are a good kid.
The High School Hustler is the positive adolescent version of the Mouthy Kid. Usually they're regarded as a good kid by almost all adults save those whose authority they directly challenge — and they can maintain that camouflage even under fire.
They are the ideological nemesis of Dean Bitterman. If they grow up and joins a Five-Man Band they'll either be The Leader (a type 1: mastermind) or if the The Leader is The Hero they'll be The Lancer to foil their purity. Other possibilities are The Face or The Smart Guy who comes up with the sneaky plans. When they graduate high school, they may become a Frat Bro upon entering college, but any fraternity they join will usually see them 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.
- 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.
- Kiriko and Sawamura from Harlem Beat often gamble on the high school basketball team's games.
- Shouko Yamanobe from Mamotte Shugogetten makes her debut as a hustling Delinquent, but is redeemed via her interactions with the Magical Girlfriend Shaorin. Henceforth she decides to devote her Zany Schemes to help Shao realize her feelings for Unlucky Everydude Tasuke.
- 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.
- 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.
- Enrique from Five Weapons shows up the five weapon club at the school without fighting or using weapons but not actually breaking any rules, earning him the scorn of the teachers and the respect of his peers.
- Gotham Academy: Colton Rivera is the guy to go to if a Gotham Academy student wants to purchase fireworks or get something the headmaster has confiscated stolen back. He's a known mess though, rather than a "cool kid", and is always on the verge of getting expelled.
- Bartleby from Accepted is a college example. He got his start with making fake IDs during high school, and then manages to completely fool his parents into thinking that the fake college South Harmon is real.
- Better Luck Tomorrow puts a twist on this trope by making the hustlers Asian honor-roll students. Their schemes run the gamut from selling stolen test answers to murder.
- Dave in The Burning, who manages to get his hands on stuff like adult magazines and condoms to bring back to the cabin he shares with the other older male campers.
- 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.
- Charlie Bartlett: A High School Hustler becomes an underground school psychiatrist!
- Zeke Tyler in The Faculty, a delinquent with a Cool Car who sells his classmates such items as condoms, VHS tapes containing nude scenes of popular teen actresses (or so he claims), and most critically for the purposes of the story, a homemade drug that, as it turns out, is highly toxic to the aliens.
- Ferris Bueller in Ferris Bueller's Day Off is a classic example. It's not clear how much hustling he does in the day to day, but he's apparently well-liked by all the cliques at school and has worked out scams on his parents and school down to an artform.
- In The Hole, Liz's original story portrays Martyn as this; able to get hold of anything for a price, including the keys to the bunker. Later events indicate that this is a complete fabrication on Liz's part; part of her plan to frame Martyn.
- Gary Valentine of Licorice Pizza starts two businesses in an actual storefront (the same one, consecutively), a waterbed store and a pinball arcade, before his 16th birthday.
- Droz, played by Jeremy Piven, in PCU. One scene has him selling term papers to a group of students whose papers were wiped when the computer lab went dark.
- Creepy example: Roger Corman's Rock 'n' Roll High School features Clint Howard (who at 20 but balding ends up 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.
- The Adventures of Tom Sawyer: The eponymous Tom Sawyer is an irascible trickster who most famously gets out of his chore of whitewashing fences by convincing other kids to pay him for the privilege of doing it for him.
- When he was in middle school, 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 bet using stolen money from his father's wallet threatened Izaya with a knife. Shinra stepped in to receive the blow. In return for telling people that it was actually Izaya who did it, Izaya vowed to make the stabber regret his move for his entire life. Knowing Izaya, it probably worked. All too well.
- The Great Greene Heist: Jackson is never out for personal profit, but is a Danny Ocean-esque figure who loves performing "heists" and pranks to help his friends and frustrate his enemies. It runs in his family.
- Harry Potter: Fred and George Weasley, particularly in their later years at school. Order of the Phoenix reveals that they're not the only ones on campus, and seem to have better morals that some of the others when Hermione has to go around confiscating black market brain stimulants sold by some of the others, none of which work and at least one of which was somewhat toxic. Harry ends up giving them a sizable startup investment, which allows them to graduate to a successful business venture as adults.
- Haruhi Suzumiya: 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 Intelligence Agency... and drags an upperclassman out. No problem.
- No Coins, Please: Preteen Artie Geller is an opportunistic entrepreneur/con artist who has a new moneymaking racket at every new stop of the summer-long road trip.
- Middle School: Rafe aspires to be a middle school example. He sells soda from his locker, even though no sugary drinks are allowed at school.
- P. G. Wodehouse's Psmith starts as this, and arguably maintains it into adulthood, becoming a master of the Indy Ploy. He notably prevents 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 looks like that'll fail, merrily confessing to the crime — even though he didn't do it either.
- The central character in a couple of Wodehouse's earlier school stories is Frederick Wackerbath Bradshaw, who's similarly unscrupulous in his methods and brilliant in avoiding punishment, but lacks the heart of gold. As the introduction to the first story explains, in adult life he became a notorious fraudster.
- Smythe from the Robert A. Heinlein juvenile Red Planet, who manipulates Jim and Frank into paying him to do favors for them.
- Squib of 15/Love is a Jerk with a Heart of Gold and borderline Manipulative Bastard who lives 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 is far from stupid, and wins more often then not.
- 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. Even before this claim to infamy, she somehow convinces the entire school (students and faculty) that she has a twin sister suffering from a horrible illness. Even though the two are never seen together, the disease is never elaborated upon, and her twin is also apparently assigned homework and tests, this all goes off with out a hitch. She holds a fake fundraiser, pockets the money, and kills off her fake twin.
- Griff Hawkins on Boy Meets World organizes pro wresting matches in the school's gymnasium in one episode. He also gets Robert Goulet to sing at his ensuing detention.
- The Brady Bunch: In the Season 3 episode "My Sister Benedict Arnold", Greg views classmate Warren Mullaney as one of these — a smooth-talking, slick-acting con artist who lies, cheats, and uses other Social Engineering tricks to get his way and satisfy his goals any way possible, even if by outright cheating... this after Greg loses (at least) a class election and a spot on the first-string basketball team to Warren.
- In the Broad City episode "Pu$$y Weed," Abbi buys pot from an adolescent drug dealer who sells a wide variety of products and offers to sell her three pages of his dad's oxycodone prescription for $500.
- 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".
- Degrassi: Joey Jeremiah from the various series, although his schemes fail as often as they succeed. In Degrassi: The Next Generation, it is revealed that he became a used-car salesman when he grew up.
- Diff'rent Strokes: The Season 8 episode "Arnold's Tangled Web" sees Spider, an adult version of the High School Hustler, offer his services to high school students who want to avoid trouble. This con artist uses the Hamburger Haven as his base of operations, and in this episode offers to forge Arnold's report card to conceal a poor grade in geometry. When it almost backfires on Arnold — Drummond thinks that Arnold is performing so well in the class that he wants to put him in an advanced placement course -– he turns to Spider to pose as his guidance counselor. However, Drummond is on to Spider from the git-go (but doesn't let on), springing a web of his own before exposing Spider as a liar and cheat... and when Arnold finally admits the truth, Drummond kicks Spider out and warns him that the police will be called if he ever hears of him preying on teenagers again.
- Luke "Gonch" Gardener from Grange Hill, although he's more a wanna-be in this trope than a full-fledged member because his endless money-making schemes rarely make any profit.
- Happy Days: The Fonz is occasionally this, operating out of the Men's Room at Arnold's. This is even lampshaded when, after the place is burnt down and rebuilt, he's given an actual office desk in there. Ew.
Fonz: Step into my office. [bangs open bathroom door, sending guys using it scurrying]
- "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] Two for six bucks.
Carly: And do they contain quality meat?
Ripoff Rodney: No they do not.
- Francis from Malcolm in the Middle used to be a scheming student who was rebellious towards authority students, and remains so in military school.
- Radar O'Reilly of M*A*S*H fits this trope in a military setting. The initially teenaged Company Clerk is constantly making trades, notably in one episode to secure a supply of tomato juice for Col. Potter (who had forgotten that he's allergic to it).
- 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.
- Our Miss Brooks: Walter Denton, who's the bane of Principal Osgood Conklin's existence. Not least because Walter is dating Mr. Conklin's Harriet. On several occasions, Mr. Conklin is the victim of Walter's pranks. For example:
- In "Cure That Habit", Walter applies to an alcoholism treatment program in Mr. Conklin's name; Hilarity Ensues when the president of the company warns the head of the board of education that Mr. Conklin is a hopeless drunk.
- "Wild Goose" has Walter trick Mr. Conklin into thinking that he's won a free TV from Sherry's Department Store. Hilarity Ensues as Mr. Conklin sends Miss Brooks to pick up his "prize".
- In "Space, Who Needs It?", Walter hides a shotgun pellet and buckshot in Mr. Conklin's homemade telescope. Mr. Conklin thinks he's discovered a new planet and her three moons, which he immediately christens "Conklin Junior". Walter then uses a toy flying saucer and wind-up space men to make Mr. Conklin think Madison is being invaded by space aliens.
- Parker Lewis from Fox's Parker Lewis Can't Lose, sometimes said to be the real TV adaptation of Ferris Bueller's Day Off, rather than the deservedly short-lived TV series Ferris Bueller. He's a rather sympathetic example in that many of his schemes are designed to help others (like getting Kubiak into college, or helping Mikey talk to a girl he likes). The fact that he often benefits himself is just a bonus. He also has lines he won't cross, like altering grades.
- Split between two characters in Press Gang: Spike Thompson is the cool, in-control aspects, while Colin Matthews is the teenaged Honest John.
- Saved by the Bell:
- Zack Morris from the original Saved by the Bell is so good at pulling off ridiculous schemes that he almost qualifies as The Great Gazoo. He's so well-equipped for and good at hustling that he even has his own cellphone! He is also revealed to have some issues from his often-absentee businessman father.
- Saved by the Bell: The New Class:
- Scott, as he's an Expy of Zack mentioned above. He's not quite as extreme (he lacks a phone of his own for one thing), but he's still a schemer out to make money, impress cute girls and slide by with as little work as possible.
- Later seasons has Ryan, who's more or less a Suspiciously Similar Substitute to Scott. It's even mentioned In-Universe early in Season 3 by fellow student Maria, due to her having been with him longer as fellow classmates and, therefore, more privy to his tendency to scheme for what he wants. That said, most of his schemes end up failing, for one reason or another.
- Maeve in Sex Education makes scratch selling pre-packaged essays, and she kicks off the series' plot by exploiting Otis's talents for back-alley sex therapy. She's not a Lovable Rogue, though, just an emancipated minor living in near-poverty who really needs money.
- Shake it Up: Deuce Martinez is a main character and good friend of the protagonists who can sell anything to anybody.
- Star Trek: Deep Space Nine: Nog, a young Ferengi from a Proud Merchant Race, exemplifies this trope. Here are a few examples:
- In one episode, he helps Chief O'Brien find a much-needed graviton stabilizer through a Chain of Deals, including trading Captain Sisko's desk, until he acquires the graviton stabilizer and gets back Sisko's desk. In the end, everyone has what they need.
- In the episode "Progress," Nog partners with Jake to make a profit on some unwanted Yamok sauce. The pair execute a Chain of Deals, but each exchange earns them only another seemingly worthless product. After trading for some semingly worthless Bajoran land, they discover that their land has suddenly become desirable, so they sell it to Quark at a hefty profit.
- 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."
- The Wire:
- The fourth season gives us Randy, a middle school version of this trope who cleverly does everything from buying candy in bulk and reselling it to his classmates to standing up for a new teacher and then swiping a batch of hall passes from the teacher's desk when he's distracted.
- DVD extras also show us the past of drug kingpin "Proposition" Joe Stewart, generally called Prop Joe. The extra scene shows Prop Joe selling stolen test answers to a group of his fellow classmates. First he deflects their threats to simply beat him up and pay nothing for the answers by pointing out that there are more tests in other subjects coming up, and if they take that approach they won't get anything. Then when they only pay him half the agreed-upon price, he promptly turns around and sells the teacher information on who'll be cheating on the test to make up for the shortfall.
- Veronica in Heathers offers her services forging documents so she can join the titular Girl Posse (the original film only implies this). In a subversion, she does it for popularity and security rather than money, and soon gets tired with her talents being exploited for petty pranks. Then taken to much darker extremes when J.D.]starts employing her skills to cover up actual murder.
- Jimmy Hopkins from Bully may be a surly punk, but underneath his delinquent attitude, he wants the cliques of the school to stop fighting and for everyone to stop bothering him. He succeeds eventually and has them all eating out of his hand, until it all goes to rats again, courtesy of a deconstructed version of this trope, Gary Smith. As it turns out, the only guy who is better at getting the entire school to eat out of his hand has to be a manipulative prick and an unstable psychopath to do so.
- Monty is a Kindergarten Hustler who serves as the game's shop. He can sell you a voice recorder, cigarettes, and much more, and he also takes custom requests such as reading notes for kids who don't know how to read yet and molding keys.
- Kindergarten 2 introduces Carla, the resident hustler at the new school the cast is transferred to. Unlike Monty, she's more in the business of doing favours, such as sneaking contraband into the school or causing distractions. Nevertheless, she still considers him an intruder on her turf, and in the mission "The Hitman's Potty Guard", she tasks the player with dismantling his wheelchair to send him a warning.
- Both Vera Oberlin and Valerie the cat girl from Monster Prom. Vera's an Alpha Bitch constantly on the lookout for a new scam, while Valerie just sells random junk. They're adopted sisters.
- Gino in Joe vs. Elan School, both before and during his incarceration at Elan. Joe describes Gino's backstory getting rich from "pretty much every hustle that was around and available to a kid in New York City," and talks about the ways Gino uses his smarts to turn Elan's rules against other inmates.
- Spicy Nun in Little Nuns will monetize everything she possibly can, from running gambling rings to opening a bank among the younger nuns. Granted, the currency is cookies, but it still fits the spirit of the trope.
- Whenever he's not on a job he's about to be fired from, Jonesy from 6teen comes up with "get rich quick" schemes, which often fail. Many of them tend to involve the "Job of the Week" he gets fired from, naturally as a result of his bosses finding out what he's up to.
- 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.
- Big Gino from Hey Arnold!, who fronts an elementary school organized crime syndicate.
- Kevin Harnisch from O'Grady practically makes a religion out of pulling schemes.
- TJ is an elementary variety, constantly outfoxing adult authorities like Miss Finster.
- The actual hustling aspect was given to the "Hustler Kid". He is able to offer the students of the school a wide range of products such as trivial toys and food, often discretely.
- The Twisted Tales of Felix the Cat: Back when he attended High School, Bet-a-Billion-Bill used to run a gambling ring at school and win everything his classmates ever waged.