Fresh

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. 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:
"Corky: You're just a little kid in way over his head, 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."
 * Anti Hero: Type IV, but it's not like Fresh has much of a choice. He's up against opponents far stronger than he is.
 * Ax Crazy: Jake. Losing at a basketball game is grounds for shooting his opponent and anyone standing to close on the playground.
 * Beneath Suspicion: Even Estaban, 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
 * Berserk Button: 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.
 * Bittersweet Ending: 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.
 * Broken Pedestal: Fresh initially idolizes the gangster lifestyle and plans to become a big shot too. After  he gives up on it. HARD.
 * The Chessmaster: Fresh, natch. Both a real chessplayer and a manipulator.
 * Chekhov's Gun: Estaban's obsession with Fresh's sister, Corky's paranoia towards his own gang members, the cop's buisness card.
 * Chekhov's Classroom: Sam's chess lessons.
 * Chess Motifs: 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.
 * Heroic BSOD: Two for Fresh.
 * Friend to All Living Things: Aunt Frances. Fresh's sister actually doesn't give a damn about her kindness and love because she knows she loves everyone.
 * Gone Horribly Right / My God What Have I Done: Fresh's plan worked out great.
 * Its Personal
 * Just a Kid: 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.
 * Nietzsche Wannabe: 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.
 * No Holds Barred Beatdown: "You're the man, Jake!"
 * Orgy of Evidence: Estaban tries to point out this trope
 * Pay Evil Unto Evil: The men Fresh goes after are truly nasty human beings, and Fresh's plan involves them meeting nasty ends.
 * The Plan: Fresh's plan to get himself and his sister out of trouble while avenging himself on his enemies.
 * Mostly a Batman Gambit though. It wouldn't have helped Fresh if the bad guys hadn't stopped him exactly as they did.
 * And it's a borderline Gambit Roulette, although the plan's reliance on established character flaws and Fresh's Just a Kid status is at least justified.
 * Reverse Psychology: Fresh tells Chuckie to keep quiet that they're going to be transporting cocaine for heroine dealer Estaban. He naturally brags about everyone he meets about this, drawing the attention of the cocaine dealer Corky, exactly as planned.
 * Smart People Play Chess: Fresh's skill at chess is connected to his genius in other areas.
 * Too Dumb to Live: Chuckie.
 * : Fresh's ultimate goal, for him and his sister.
 * Would Hurt a Child: With a chain no less.