I want to run games where the players are scoundrels in the old hardboiled pulp sense. Sessions would be episodic one shots of different jobs: gunrunning, heists, navigating the authorities... I want to keep the tone mercenary and maverick. Staying ahead of the law is never something that can be achieved for certain, intrigue and complications will arise organically without cliche heist-movie style double-triple crosses.

Does anyone have experience running this sort of play? How can the desperate tone be maintained?