History Main / HighSchoolHustler

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 ChainOfDeals and make it work for everybody. He can pull off a BavarianFireDrill without getting his bluff called. Often he's out for himself, but frequently willing to help those in need.

The character type is predominantly male. He is the ideological nemesis of DeanBitterman. If he grows up and joins a FiveManBand he'll either be TheLeader (a type 1: mastermind) or if the TheLeader is TheHero he'll be TheLancer to foil his purity. Other possibilities are TheFace or TheSmartGuy who comes up with the sneaky {{plan}}s. When he graduates high school, he ''may'' become a FratBro 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 Jock}}s who make up the other fraternities.

* Kira Sakuya from ''Manga/AngelSanctuary'' would fit this to a T, except [[CosmicHorrorStory not really]].
* [[http://nomimushi.livejournal.com/4423.html In the novel]], a precocious middleschool hustler!Orihara Izaya of ''LightNovel/{{Durarara}}'' was the bookie of the school's betting pool for baseball. It didn't run so smoothly when [[spoiler: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.]]
* Hiruma of ''Manga/{{Eyeshield 21}}'' is an example of what happens when the High School Hustler becomes a DrillSergeantNasty 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.
* Negiri from ''Manga/FutabaKunChange''. Originally nothing more than a CaptainErsatz of the more famous Nabiki Tendo (above) she quickly became a more sympathetic, friendly and professional example of this trope.
* Kiriko and Sawamura from ''Manga/HarlemBeat''.
* ''LightNovel/HaruhiSuzumiya'': 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 [[FiveManBand SOS Brigade]] end up in a ''better'' situation by the end of the episode. Her peculiar brand of [[JerkWithAHeartOfGold conscientious amorality]] tends to help with this. The fact that [[spoiler:she is possibly ''God'']] probably helps a lot more. However, this trope is probably played straight. [[spoiler: Her "recruiting" of Asahina in Disappearance (where she can't [[RealityWarper 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. ]]
* Shouko Yamanobe from ''Manga/MamotteShugogetten'' made her debut as a hustling [[{{Delinquents}} Delinquent]], but was redeemed via her interactions with the MagicalGirlfriend Shaorin. Henceforth she decided to devote her [[ZanyScheme Zany Schemes]] to [[ShipperOnDeck help]] Shao [[ObliviousToLove realize]] her feelings for UnluckyEverydude Tasuke.
* Tamaki from ''Manga/OuranHighSchoolHostClub'' 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.

* Roger the Dodger from ''ComicBook/TheBeano''
* Winker Watson (the Wangler) from ''ComicBook/TheDandy''.
* 'Young Arfur' from ''School Fun'' (later ''Comicbook/{{Buster}}''), who was a kid version of [[Series/{{Minder}} Arthur Daley]].
* The protagonist of ''ComicBook/FiveWeapons'', with shades of BatmanGambit and MagnificentBastard.
* ''ComicBook/GothamAcademy'': Colton Rivera is they 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.
* ''ComicBook/{{Shazam}}'': Freddy, in the New 52 reboot. Not only is it near-character assassination compared to his Golden Age self but he's not even good at it (having sold a forged doctor's note for a gynecological disease to a boy).

* College example: Bartleby in ''Film/{{Accepted}}''.
* ''Film/BackToTheFuture'': 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 more of this type of character, though.
* ''Film/BetterLuckTomorrow'' puts a twist on this trope by making the hustlers Asian honor-roll students. Their schemes run the gamut of selling stolen test answers to murder.

* Mud Himmel from ''Film/CampNowhere'' is the junior high equivalent.
* In the beginning of ''Film/CatchMeIfYouCan,'' 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. [[spoiler: She resists his implication at first, then surreptitiously takes his advice.]]

* Max in ''Film/MaxKeeblesBigMove'', to the point that critics panned it mostly because he was a Bueller ripoff.
* Droz, played by Jeremy Piven, in ''Film/{{PCU}}''. One scene has him selling term papers to a group of students whose papers were wiped when the computer lab went dark.
* ''Film/RealGenius'': Chris Knight is a prototypical example of this trope.

* In ''Film/{{Rushmore}}'' Max Fisher is the low key version of this trope. Actually a {{Deconstruction}} of the very concept.
* ''Film/VanWilder'' is what happens when this character successfully becomes BigManOnCampus. And then stays there for almost a decade.

* ''Literature/HarryPotter'': Fred and George Weasley, particularly in their later years at school. ''[[Literature/HarryPotterAndTheOrderOfThePhoenix Order of the Phoenix]]'' reveals 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.
* The unnamed diarist (later revealed to be Brian Boyes, see below) in the ''How To Handle Grownups'' series by Jim Eldridge.
* The protagonist is a variant in ''Literature/LittleBrother''.
* Bruno and Boots from the ''Literature/MacdonaldHall'' series.

* Creator/PGWodehouse's Literature/{{Psmith}} started as this, and arguably maintained it into adulthood, becoming a master of the IndyPloy. 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.
* Smythe from the Creator/RobertAHeinlein juvenile ''Literature/RedPlanet''.
* The eponymous Luther Wesley "Soup" Vinson from Creator/{{Robert Newton Peck}}'s ''Literature/{{Soup}}'' series is an Elementary School Hustler.
* Creator/RudyardKipling's Stalky, the hero of various BoardingSchool stories collected in the book ''Literature/StalkyAndCo''.
* Raven from ''Literature/VampireKisses'' seems to have shades of this.
* Coyote from "White Lines on a Green Field" by Creator/CatherynneMValente.

* Squib of ''Series/FifteenLove'' was a JerkWithAHeartOfGold and borderline ManipulativeBastard 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.
* Maeby in ''Series/ArrestedDevelopment'', 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 RefugeInAudacity.
** 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.
* Brian Arthur Derek Boyes in ''Series/BadBoyes''.
* Griff Hawkins on ''Series/BoyMeetsWorld'' takes this trope UpToEleven, organizing pro wresting matches in the schools gymnasium in one episode.
** He also got Robert Goulet to sing at his ensuing detention.
* ''Series/TheBradyBunch'': 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 SocialEngineering 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.

* ''Series/BuffyTheVampireSlayer'': Buffy and the rest of the Scoobies often end up in this role.
* In the ''Series/{{Community}}'' episode "[[Recap/CommunityS2E09ConspiracyTheoriesAndInteriorDesign 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''... [[spoiler: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".
* ''Series/{{Degrassi}}'': Joey Jeremiah from the various series, although his schemes fail as often as they succeed. (In ''Series/DegrassiTheNextGeneration'', it is revealed that he became a [[HonestJohnsDealership used-car salesman]] when he grew up.)
* ''Series/DiffrentStrokes'': The Season 8 episode "Arnold's Tangled Web" saw Spider, an adult version of the High School Hustler, offer his services to high school students who want to avoid trouble. This con artist used the Hamburger Haven as his base of operations, and in this episode offered 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 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.
* Will Smith in ''Series/TheFreshPrinceOfBelAir''.
* Luke "Gonch" Gardener from ''Series/GrangeHill'', although he was more a wanna-be in this trope than a full-fledged member because his endless money-making schemes rarely made any profit.

-->'''Fonz:''' Step into my office. (bangs open bathroom door, sending guys using it scurrying)
* Brad's friend Jason on ''Series/HomeImprovement''.

-->'''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.
* ''Series/ItsYourMove'': Matthew Burton (played by Jason Bateman).
* OlderThanTheyThink example -- Eddie Haskell from ''Series/LeaveItToBeaver''.
* Francis from ''Series/MalcolmInTheMiddle''.
* Radar O'Reilly of ''[[Series/{{Mash}} 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).
* In "Life Skills," a fourth-season episode of ''Series/TheMiddle'', 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.
* Parker Lewis from Fox's ''Series/ParkerLewisCantLose,'' sometimes said to be the [[BetterByADifferentName real TV adaptation]] of ''Film/FerrisBuellersDayOff'', rather than the deservedly short-lived [[RecycledTheSeries TV series]] ''Ferris Bueller''.
* ''Radio/OurMissBrooks'': Walter Denton, who was the bane of Principal Osgood Conklin's existence. Not least, because Walter was dating Mr. Conklin's Harriet. On several occasions, Mr. Conklin was the victim of Walter's pranks. For example:

** "Wild Goose" has Walter trick Mr. Conklin into thinking that he's won a free t.v. from Sherry's Department Store. HilarityEnsues as Mr. Conklin sends Miss Brooks to pick up his "prize".

* ''Series/ThePhilSilversShow'': Sgt. Bilko (Phil Silvers) was a middle aged version, with an army base as his "high school" and its colonel as the DeanBitterman.
* Split between two characters in ''Series/PressGang'': Spike Thompson was the cool, in-control aspects, while Colin Matthews was the teenaged HonestJohn.
* Zack Morris of ''Series/SavedByTheBell'' was ''so'' good at pulling off ridiculous schemes that he almost qualifies as The GreatGazoo. He was so well-equipped for and good at hustling, he even [[StatusCellphone has his own cellphone!]] He is also revealed to have some issues from his often-absentee businessman father.
* ''Series/SavedByTheBellTheNewClass'':
** Scott, as he's an {{Expy}} of [[Series/SavedByTheBell Zack]] mentioned above.
** Later seasons has Ryan, who's more or less a SuspiciouslySimilarSubstitute to Scott. It's even [[LampshadeHanging mentioned]] InUniverse 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 ''Series/SexEducation'' makes scratch selling pre-packaged essays, and she kicks off the series plot by exploiting Otis' talents for back-alley sex therapy. She's not a LovableRogue, though, just an emancipated minor living in near-poverty, who really needs money.

* ''Series/StarTrekDeepSpaceNine'': Nog, a Ferengi character.

** 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.

** 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 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!
* Cam Dunleavey in ''Series/TheZackFiles''.

[[folder:Newspaper Comics]]
* TJ from ''{{ComicStrip/Luann}}'' is a young adult version of this. He's aged out of school, but the personality remains.

[[folder:Theatre]]
* Veronica in ''Theatre/{{Heathers}}'' offers her services forging documents so she can join the titular GirlPosse (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 [[BastardBoyfriend J.D.]] starts employing her skills to cover up actual ''murder''.
[[/folder]]

* Jimmy Hopkins from ''Videogame/{{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, [[spoiler: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.]]
* Both Vera Oberlin and Valerie the cat girl from ''VisualNovel/MonsterProm''. Vera's an AlphaBitch constantly on the lookout for a new scam, while Valerie just sells random junk. [[spoiler: They're adopted sisters]].
* Raz of ''VideoGame/{{Psychonauts}}'' has elements of this in his character, although he is younger than average. The bad guy of the game is [[spoiler:Coach Oleander]], the kind of adult that any High School Hustler would be against.

* Jonesy of ''WesternAnimation/{{Sixteen}}'' qualifies, when he's not getting caught at least.
* Max Goof in ''WesternAnimation/GoofTroop'' 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 Scheme}}s either turn into [[ShaggyDogStory Shaggy Dog Stories]] (with his [[NoRespectGuy hapless friend]] suffering for it) or end up putting him in [[DistressedDude serious danger]] because of his [[FearlessFool severe recklessness]]. He is fairly self-centered and ambitious but generally is a good person and will help out others.

* ''{{Humphrey}}'': Kevin Harnisch from ''O'Grady'' practically makes a religion out of pulling schemes.
* TJ from ''WesternAnimation/{{Recess}}'' certainly qualifies, though the actual hustling aspect was given to the "Hustler Kid".

* The main character from ''WesternAnimation/WhatsWithAndy?'', who is also a PrinceOfPranksters.

[[folder: Theatre]]

* Radar O'Reilly of ''[[Series/{{Mash}} 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).
* Luke "Gonch" Gardener from ''Series/GrangeHill'', although he was more a wanna-be in this trope than a full-fledged member because his endless money-making schemes rarely made any profit.

* ''Series/HappyDays'': 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)

* In the ''Series/BroadCity'' 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.
* Maeve in ''Series/SexEducation'' makes scratch selling pre-packaged essays, and she kicks off the series plot by exploiting Otis' talents for back-alley sex therapy. She's not a LovableRogue, though, just an emancipated minor living in near-poverty, who really needs money.

* Raz of ''VideoGame/{{Psychonauts}}'' has elements of this in his character, although he is younger than average. The bad guy of the game is [[spoiler:Coach Oleander]], the kind of adult that any High School Hustler would be against.

* Big Gino from ''WesternAnimation/HeyArnold'', who fronts an elementary school organized crime syndicate.

* Jonesy of ''WesternAnimation/{{Sixteen}}'' qualifies, when he's not getting caught at least.
* Max Goof in ''WesternAnimation/GoofTroop'' 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 Scheme}}s either turn into [[ShaggyDogStory Shaggy Dog Stories]] (with his [[NoRespectGuy hapless friend]] suffering for it) or end up putting him in [[DistressedDude serious danger]] because of his [[FearlessFool severe recklessness]]. He is fairly self-centered and ambitious but generally is a good person and will help out others.
* ''WesternAnimation/TheTwistedTalesOfFelixTheCat'': 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.

* Nabiki Tendo from ''Manga/RanmaOneHalf'', though more of a [[TheBarnum Barnum]] than not. She rarely (if ''ever'') cares about the consequences other people have to face for her actions, though.
* ''LightNovel/HaruhiSuzumiya'': 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 [[FiveManBand SOS Brigade]] end up in a ''better'' situation by the end of the episode. Her peculiar brand of [[JerkWithAHeartOfGold conscientious amorality]] tends to help with this. The fact that [[spoiler:she is possibly ''God'']] probably helps a lot more. However, this trope is probably played straight. [[spoiler: Her "recruiting" of Asahina in Disappearance (where she can't [[RealityWarper 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. ]]
* Tamaki from ''Manga/OuranHighSchoolHostClub'' 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 ''Manga/FutabaKunChange''. Originally nothing more than a CaptainErsatz of the more famous Nabiki Tendo (above) she quickly became a more sympathetic, friendly and professional example of this trope.
* Shouko Yamanobe from ''Manga/MamotteShugogetten'' made her debut as a hustling [[{{Delinquents}} Delinquent]], but was redeemed via her interactions with the MagicalGirlfriend Shaorin. Henceforth she decided to devote her [[ZanyScheme Zany Schemes]] to [[ShipperOnDeck help]] Shao [[ObliviousToLove realize]] her feelings for UnluckyEverydude Tasuke.

* [[http://nomimushi.livejournal.com/4423.html In the novel]], a precocious middleschool hustler!Orihara Izaya of ''LightNovel/{{Durarara}}'' was the bookie of the school's betting pool for baseball. It didn't run so smoothly when [[spoiler: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 ''Film/CatchMeIfYouCan,'' 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. [[spoiler: She resists his implication at first, then surreptitiously takes his advice.]]
* Ferris Bueller in ''Film/FerrisBuellersDayOff'' 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.
* ''Film/BetterLuckTomorrow'' puts a twist on this trope by making the hustlers Asian honor-roll students. Their schemes run the gamut of selling stolen test answers to murder.

* Creepy example: Creator/RogerCorman's ''Film/RockAndRollHighSchool'' features Creator/ClintHoward (at 20, an unfortunate mix of DawsonCasting and YoungerThanTheyLook) as the enterprising Eaglebauer, who resides in a BiggerOnTheInside 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.

* ''Film/VanWilder'' is what happens when this character successfully becomes BigManOnCampus. And then stays there for almost a decade.
* Droz, played by Jeremy Piven, in ''Film/{{PCU}}''. One scene has him selling term papers to a group of students whose papers were wiped when the computer lab went dark.

* In ''Film/{{Rushmore}}'' Max Fisher is the low key version of this trope. Actually a {{Deconstruction}} of the very concept.
* Max in ''Film/MaxKeeblesBigMove'', to the point that critics panned it mostly because he was a Bueller ripoff.
* ''Film/RealGenius'': Chris Knight is a prototypical example of this trope.
* Mud Himmel from ''Film/CampNowhere'' is the junior high equivalent.

* Dave in ''Film/TheBurning'', 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.

* ''Literature/HarryPotter'': Fred and George Weasley, particularly in their later years at school. ''[[Literature/HarryPotterAndTheOrderOfThePhoenix Order of the Phoenix]]'' reveals 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.
* Coyote from "White Lines on a Green Field" by Creator/CatherynneMValente.

* The protagonist is a variant in ''Literature/LittleBrother''.
* The unnamed diarist (later revealed to be Brian Boyes, see below) in the ''How To Handle Grownups'' series by Jim Eldridge.
* Bruno and Boots from the ''Literature/MacdonaldHall'' series.
* ''Literature/MiddleSchool'': Rafe aspires to be a middle school example. He sells soda from his locker, even though no sugary drinks are allowed at school.
* Raven from ''Literature/VampireKisses'' seems to have shades of this.
* Creator/RudyardKipling's Stalky, the hero of various BoardingSchool stories collected in the book ''Literature/StalkyAndCo''.

* Parker Lewis from Fox's ''Series/ParkerLewisCantLose,'' sometimes said to be the [[BetterByADifferentName real TV adaptation]] of ''Film/FerrisBuellersDayOff'', rather than the deservedly short-lived [[RecycledTheSeries TV series]] ''Ferris Bueller''.
* Zack Morris of ''Series/SavedByTheBell'' was ''so'' good at pulling off ridiculous schemes that he almost qualifies as The GreatGazoo. He was so well-equipped for and good at hustling, he even [[StatusCellphone has his own cellphone!]] He is also revealed to have some issues from his often-absentee businessman father.
* ''Series/SavedByTheBellTheNewClass'':
** Scott, as he's an {{Expy}} of [[Series/SavedByTheBell Zack]] mentioned above.
** Later seasons has Ryan, who's more or less a SuspiciouslySimilarSubstitute to Scott. It's even [[LampshadeHanging mentioned]] InUniverse 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.

* ''Series/ShakeItUp'': Deuce Martinez is a main character and good friend of the protagonists who can sell anything to anybody.
* ''Series/{{Degrassi}}'': Joey Jeremiah from the various series, although his schemes fail as often as they succeed. (In ''Series/DegrassiTheNextGeneration'', it is revealed that he became a [[HonestJohnsDealership used-car salesman]] when he grew up.)
* ''Series/VeronicaMars'' 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 ''Series/ParkerLewisCantLose'' 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."
* ''Series/StarTrekDeepSpaceNine'': Nog, a Ferengi character.
** In one episode, he helps Chief O'Brien find a much-needed graviton stabilizer through a [[ChainOfDeals 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.
* Francis from ''Series/MalcolmInTheMiddle''.

* Will Smith in ''Series/TheFreshPrinceOfBelAir''.
* ''Series/BuffyTheVampireSlayer'': Buffy and the rest of the Scoobies often end up in this role.

* Maeby in ''Series/ArrestedDevelopment'', 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 RefugeInAudacity.
* Squib of ''Series/FifteenLove'' was a JerkWithAHeartOfGold and borderline ManipulativeBastard 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 ''Series/BoyMeetsWorld'' takes this trope UpToEleven, organizing pro wresting matches in the schools gymnasium in one episode.
** He also got Robert Goulet to sing at his ensuing detention.
* Brad's friend Jason on ''Series/HomeImprovement''.
* In the ''Series/{{Community}}'' episode "[[Recap/CommunityS2E09ConspiracyTheoriesAndInteriorDesign 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''... [[spoiler: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".
* Brian Arthur Derek Boyes in ''Series/BadBoyes''.
* "Rip-off" Rodney of ''Series/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 ''Series/TheMiddle'', 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.

The character type is predominantly male. He is the ideological nemesis of DeanBitterman. If he grows up and joins a FiveManBand he'll either be TheLeader (a type 1: mastermind) or if the TheLeader is TheHero he'll be TheLancer to foil his purity. Other possibilities are TheFace or TheSmartGuy who comes up with the sneaky {{plan}}s. If the lead male in a SixStudentClique isn't TheAce, he'll usually be this...or some combination of the two. When he graduates high school, he ''may'' become a FratBro 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 Jock}}s who make up the other fraternities.

* Hiruma of ''Manga/{{Eyeshield 21}}'' is an example of what happens when the HighSchoolHustler becomes a DrillSergeantNasty 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.

* Raz of ''VideoGame/{{Psychonauts}}'' has elements of this in his character, although he is younger than average. The bad guy of the game is [[spoiler:Coach Oleander]], the kind of adult that any HighSchoolHustler would be against.

* Veronica in ''Theatre/{{Heathers}}'' offers her services forging documents so she can join the titular GirlPosse (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.

* ''Literature/HarryPotter'': Fred and George Weasley, particularly in their later years at school. ''[[Literature/HarryPotterAndTheOrderOfThePhoenix Order of the Phoenix]]'' reveals 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, non of which work and at least one of which was somewhat toxic.

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* ''Series/HappyDays'': The Fonz is occasionally this, operating out of the Mens' 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.

-->--'''Ferris Bueller''', ''Film/FerrisBuellersDayOff''

* ''Series/SavedByTheBellTheNewClass''

** Later seasons has Ryan, who's more or less a SuspiciouslySimilarSubstitute to Scott above. It's even [[LampshadeHanging mentioned]] InUniverse 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.

* ''Series/SavedByTheBellTheNewClass'' has Ryan, who's more or less an {{Expy}} of [[Series/SavedByTheBell Zack]] mentioned above. It's even [[LampshadeHanging mentioned]] InUniverse 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.

* ''Series/ShakeItUp Chicago'': Deuce Martinez is a main character and good friend of the protagonists who can sell anything to anybody.

* ''ComicBook/{{Shazam}}: Freddy, in the New 52 reboot.

* Zack Morris of ''Series/SavedByTheBell'' was ''so'' good at pulling off ridiculous schemes that he almost qualifies as The GreatGazoo. He was so well-equipped for and good at hustling, he even [[TechMarchesOn has his own cellphone!]] He is also revealed to have some issues from his often-absentee businessman father.

* Ferris Bueller in ''Film/FerrisBuellersDayOff'' is a classic example.

* Droz, played by Jeremy Piven, in ''Film/{{PCU}}''.

* In the ''Series/{{Community}}'' episode "[[Recap/CommunityS2E09ConspiracyTheoriesAndInteriorDesign 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''... [[spoiler: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".

* Zack Morris of ''Series/SavedByTheBell'' was ''so'' good at pulling off ridiculous schemes that he almost qualifies as The GreatGazoo. He is also revealed to have some issues from his often-absentee businessman father.

* Perhaps the UrExample was [[Literature/TheAdventuresOfTomSawyer Tom Sawyer]].

** In one episode, he helps Chief O'Brien find a much-needed graviton stabilizer through a [[ChainOfDeals 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.\\

* ''Series/StarTrekDeepSpaceNine'': Nog, a Ferengi character. In one episode, he helps Chief O'Brien find a much-needed graviton stabilizer through a [[ChainOfDeals 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.

** 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 said teacher's desk when the teacher is distracted in order to sell them.