10. Bertha in Boxcar Bertha

Bertha Thompson (Barbara Hershey) is one of Scorsese’s most charismatic criminals because she turns rebellion into an art form—she’s not just running from the law, she’s dancing through it. Hershey plays her with a devil-may-care charm, flashing a wide, defiant grin even as she drifts from con to con, from lover to lover, from train car to train car. Unlike the cold calculation of Casino’s Ace Rothstein or the ruthless ambition of Goodfellas’ Henry Hill, Bertha’s charisma isn’t built on control—it’s built on freedom. She seduces men with the same effortless ease with which she robs them, and when she pulls off a heist, it’s not about power, but play. Even when the stakes get deadly, like when she and her crew ambush a railway boss, there’s a magnetic recklessness to her—she believes in the cause but loves the chaos. And that’s what makes her unforgettable—she’s not just a criminal, she’s an outlaw in the purest sense, laughing in the face of a world that tells her to stay in her place.