Made in 1994, this very grim film is named after its protagonist. Fresh is a young black genius living with his saintly aunt and eleven other children, in a poor neighborhood. Fresh's life is disrupted by the drug trade in several ways: working for the kingpin Esteban makes him chronically late for school, his beloved sister is an addict, and gun fights break out where school kids play. [[Creator/SamuelLJackson Samuel L. Jackson]] plays Fresh's father, a caustic chess champion whose way of relating with his son is to berate him for imperfect play. Eventually, Fresh loses too much and the time comes for him to play the dangerous adults he's working for against one another, with the goal of escaping that life at all costs.
!!This film provides examples of:
* AntiHero: Not like Fresh has much of a choice. He's up against opponents far stronger than he is.
* AxCrazy: Jake. Losing at a basketball game is grounds for shooting his opponent and anyone standing to close on the playground.
* BeneathSuspicion: Even Esteban, who knows Fresh is smart, doesn't realize the possibility that a little kid is running a scam on his own.
** Interestingly, the only one who saw through part of Fresh's gambit was his classmate and best friend. Who was understandably furious because [[spoiler: Fresh got Chuckie killed.]]
* BerserkButton: For Fresh, his sister Nichole, although he is too vulnerable to visibly lose his temper. For Esteban, it's men who hold the interest of women he thinks of as his. And Corky is (by necessity, since it's a lethal business) hypervigilant about his subordinates trying to double-deal.
* BittersweetEnding: Fresh's gambit works like a charm, but the final scene shows him sobbing uncontrolably in front of his father.
** The final move in Fresh's symbolic chess game with himself is black beating white.
* BrokenPedestal: Fresh initially [[DamnItFeelsGoodToBeAGangster idolizes the gangster lifestyle and plans to become a big shot too.]] After [[spoiler: a pointless shootout kills the girl he had a crush on,]] he gives up on it. HARD.
* TheChessmaster: Fresh, natch. Both a real chessplayer and a manipulator.
* ChekhovsGun: Esteban's obsession with Fresh's sister, Corky's paranoia towards his own gang members, the cop's business card.
** ChekhovsClassroom: Sam's chess lessons.
* ChessMotifs: A very strong presence, with certain characters represented by specific pieces. Fresh even keeps a board set up and makes moves corresponding to the plot developments.
* HeroicBSOD: Two for Fresh. [[spoiler: The first after his would-be girlfriend is killed, untill his father gives him some Chess tips that he decides to apply in the hood. The second after said ruthless application has succeeded.]]
* FriendToAllLivingThings: Aunt Frances. Fresh's sister actually doesn't give a damn about her kindness and love because she knows she loves everyone.
* GoneHorriblyRight / MyGodWhatHaveIDone: Fresh's plan worked out great. [[spoiler: He got himself and his sister out of the ghetto, at the price of betraying or arranging the deaths of everyone he ever knew except his sister and father.]]
* GuileHero: Fresh uses straight up manipulation and deception to get out of the hood. He does a number of morally questionable things in the process, though.
* JustAKid: Both played straight and subverted. Some people under-estimate Fresh because of his youth, others see him as the genius he is - and his eventual plan relies on people seeing him this way.
* NietzscheWannabe: Fresh's sister, who actually prefers the man who treats her like dirt because she feels she is worthless. Mind you, not that her alternative was any less creepy.
* NoHoldsBarredBeatdown: "You're the man, Jake!"
* OrgyOfEvidence: Esteban tries to point out this trope [[spoiler: when the police finds a gun just used in a murder and a huge bag of heroin under his mattress. It doesn't help his case that both the drugs and the gun were really Esteban's, Fresh just made sure they could be found.]]
* PayEvilUntoEvil: The men Fresh goes after are truly ''nasty'' human beings, and Fresh's plan involves them meeting nasty ends.
* ThePlan: Fresh's plan to get himself and his sister out of trouble while avenging himself on his enemies.
** Mostly a BatmanGambit though. It wouldn't have helped Fresh if the bad guys hadn't stopped him exactly as they did.
** And it's a borderline GambitRoulette, although the plan's reliance on established character flaws and Fresh's JustAKid status is at least justified.
* PunctuatedForEmphasis: "Jake's the man now. And you gonna be his number one g. HIS NUMBER! ONE! G!"
* ReversePsychology: Fresh tells Chuckie to keep quiet that they're going to be transporting cocaine for heroin dealer Esteban. He naturally brags about everyone he meets about this, drawing the attention of the cocaine dealer Corky, exactly as planned.
* ShootTheDog: Fresh manipulates events in such a way so that [[spoiler:his friend, Chuckie, will get killed in his bid to turn the gangs against each other. He also literally shoots his own dog.]]
* SmartPeoplePlayChess: Fresh's skill at chess is connected to his genius in other areas.
* TooDumbToLive: Chuckie.
* WhatTheHellHero: Fresh gets assaulted by his friend, who blames him (correctly) for [[spoiler:getting Chuckie killed.]]
* [[spoiler: WitnessProtection]]: Fresh's ultimate goal, for him and his sister. [[spoiler: Even if he has to engineer the crimes he witnesses himself.]]
* WouldHurtAChild: With a chain no less.
-->'''Corky:''' You're [[JustAKid just a little kid]] in way over his head, [[CriticalResearchFailure I know that]]. But Esteban gotta be sent a message about horning in on my business. I'm afraid you gonna have to be my little telegram.