Picture yourself settling in for a movie night-craving that perfect mix of thrill, laughs, and heart. Brad Pitt delivers it every time with characters that linger long after the credits roll. Over 30 years, fans keep returning to five absolute favorites that showcase his effortless range: the flirtatious J.D. from ‘Thelma & Louise’, the anarchic Tyler Durden from ‘Fight Club’, the unraveling Detective David Mills from ‘Se7en’, the unhinged Jeffrey Goines from ‘12 Monkeys’, and the supremely chill Cliff Booth from ‘Once Upon a Time in Hollywood’. These aren’t just roles; they’re the ones we quote, mimic, and adore.