14. Jimmy Darmody in Boardwalk Empire
Portrayed by: Michael Pitt
Dies in: "To the Lost" (Season 2, Episode 12)
The Greek tragedy that was James Darmody’s life was one cruel joke, and he knew it. A miscommunication leads him to betray his only father figure, Nucky Thompson, in favor of his biological father, the Commodore (the man who took advantage of his mother at age thirteen). Couple his approval-seeking power play with the narrative haymaker that his kooky mother made their Oedipus and Jocasta themes literal, successfully seducing and sleeping with him, and it’s clear that this poor, screwed-up kid, haunted by all that plus action in WWI, was never going to hold on to the keys to the city.
On a broadcast network series, where keeping fan-favorite characters around is at times a higher priority than organic storytelling, Jimmy and Nucky might’ve shaken hands and let bygones be bygones. But you can’t be the boss and let insubordination and assassination attempts slide with just a slap on the wrist.
It was a shock when Boardwalk killed the character who had been the co-lead for two full seasons, but what made it particularly devastating was Jimmy’s participation in his own set-up. He does everything he can to make amends with Nucky and untie the noose he spent a season tying around the man’s neck. But he knows Nucky can’t—and won’t—forgive him for real, and his resignation is palpable during what will be his last moments with his batshit mother, soon to be orphaned toddler, and best-friend/killing-machine Richard Harrow.
He drives to a nighttime rendezvous with Nucky completely unarmed, simply because he’s given up trying to force a win and accepted that he was born to lose.