Don Cheadle

The director of Devil in a Blue Dress refused to audition him, thinking he looked too young for the part. An accidental meeting at a doctor's office changed that. Cheadle spent a week in Houston researching, came back, and won Best Supporting Actor from the Los Angeles Film Critics Association for Mouse Alexander. Boogie Nights followed in 1997, and Hotel Rwanda in 2004 earned him an Oscar nomination for Best Actor. He went from being turned away at the door to landing the kind of role that resets a career.

Cheadle got the War Machine role while at his kid's laser tag birthday party. That's when Marvel called, offered a six-picture deal, and gave him two hours to decide or they'd move on. He called his wife and agent mid-game, said yes, and stepped in for Terrence Howard, who'd left over a salary dispute. He's carried that role across the MCU for over a decade. Now he's making his Broadway debut in Proof alongside Ayo Edebiri in 2026, which suggests the franchise work was always the means, not the destination.

He graduated from the California Institute of the Arts with a theater BFA in 1986, the kind of formal training most working actors skip. He'd already been playing saxophone in jazz bands and doing theater throughout a childhood spent moving from city to city. Outside acting, he's a UN Environment Programme Goodwill Ambassador who puts in actual policy appearances, not just red carpet support. His X account, meanwhile, runs entirely on chaos: deadpan non-sequiturs and absurdist posts that seem specifically designed to confuse anyone expecting a coherent celebrity presence.