LogFAQs > #977116405

Kaiji.
There's a bunch of anime and shows doing the whole protag gets involved in high risk games thing but Kaiji's the only one I like. Unique art style, narrator's fun even if you don't speak Japanese, villains are actual fuckers instead of generic wannabe cool guys on the opposing side. Luck weighs heavily, sometimes Kaiji wins, sometimes he really doesn't.

I'd also say Baccano and Yu Yu Hakusho but that's a whole bunch of typing.