Roman Roy

The youngest Roy sibling, Roman is the family clown: a Waystar executive who fires off obscene jokes in board meetings and treats his father's empire like an adult playground he's still trying to get invited into. Underneath the wisecracks is a kid desperate for his dad's approval and terrified of being taken seriously.

Culkin plays him as pure nervous energy, a man who's weaponized deflection so thoroughly he can barely say a sincere sentence without flinching. The filthy one-liners land because they're clearly armor, and the show keeps letting you glimpse the wound underneath before the joke slams back down.