ENESPT
You Can't Win

You Can't Win (2026)★ 4.4/10

US · 108 min · February 17, 2026

  • Drama

Directed by: Robinson Devor

Written by: Robinson Devor, Charles Mudede, Michael Pitt, Jack Black

The true-crime story of Jack Black, whose 1926 memoir became an unlikely bestseller upon its release and later inspired generations of counter-cultural writing.

Directed by

Robinson Devor

Written by

Robinson DevorCharles MudedeMichael PittJack Black

Cast & crew

Michael PittJack BlackJames HongOld Chinese ManJenni BradstreetChinese SleeperJim ChowChinese SleeperTony LaoChinese SleeperDavid LeongChinese SleeperHutch StellickBoy JackTed RooneyJack's FatherRobert BlancheCySkyler VerityYoung JackJeremy Allen WhiteSmilerBrandon E. JacksonPrison GuardCharles BakerFremont OlderRusty TennantDepot PolicemanWill PattonFoot and A Half GeorgeIvan MartinThe Sanctimonious KidChris LeBlancCorbettRusty SchwimmerSalt Chunk MaryRobert ZornJungle BumWilliam Warren WardJungle BumEarl AlexanderJungle BumRon LampmanJungle BumRob FinneyJungle BumArt HickmanJungle BumKen ClarkJungle BumTim HendersonJungle BumHenry MarkChew CheeAlex TerzieffWork Crew BossTodd LagesteeWork Crew GuardLouisa KrauseIrish AnnieRon OtisHotel DetectiveJohn PaulsenJunkie HusbandKathy HsiehJunkie WifeJim HamerlinckGoldtoothJames LapanStation AgentStella DiazStation Agent's WifeJulia GarnerChickenMark FullertonCanadian ConstableScottMurpheyAnatol YusefDirty DickNina AriandaMrs. AlexanderAnthony A. KungOpium Den PickpocketAlexis ScarffGhost MotherWesley ScarffBaby JackKori EnnisSalon PatronDavid BeckSalon PatronRaphael CarloTripped Bum (uncredited)Josh ChapmanAudience member (uncredited)Tony DoupeLogger (uncredited)Ronnie FeltsAudience Member (uncredited)Jay G. HillAngry logger (uncredited)Russell HodgkinsonBoxcar Bum (uncredited)Jeffrey HoughtonMiner (uncredited)Chase HumphreyAudience Member (uncredited)Jobie JamesBusinessman (uncredited)Morgen JohnsonRepo man (uncredited)Gabrielle LaneRowdy Prostitute (uncredited)Jamie LoyAudience Member (uncredited)Michele B. McGrawAudience Member (uncredited)Gavin McLeroyWolfish Boy (uncredited)Landon MorganBusinessman (uncredited)Christophe MurdockPasserby (uncredited)Melissa PangToothless Chinese Woman (uncredited)Justin PappanBoxcar Hobo (uncredited)Martin ParkHomeowner (uncredited)Diana Dee PascualProstitute (uncredited)Leland PraterPasserby (uncredited)Russell W. ReedShirtless heavyset man (uncredited)JulieAnna RohdeAudience Member (uncredited)Chandler RyanLady (uncredited)Ryan SandersConstable (uncredited)Mariah WebbWhore (uncredited)Greg WilliamsUpperclass Gentleman (uncredited)Troy WilsonPasserby (uncredited)