11. Jimmy (Michael Pitt); Boardwalk Empire

Despite being born with a metric ton of mommy and daddy issues, the tortured, doomed Boardwalk fan-favorite took a page out of father figure Nucky's book and stayed fresh during his gangster day-to-day grind. He dressed the part well, but when it came time to actual be the boss of Atlantic City, he was less successful. A lot less successful. Fatally unsuccessful. Did we mention he wore nice three-piece suits?