'Billy Bathgate' (1991)
It's surprising to think it took until the early Nineties for someone to cast Hoffman as Howard "Dutch" Schultz – it's the sort of complex part that that seems tailor-made for him like an Italian suit. In Robert Benton's adaptation of E.L. Doctorow's novel, the Jewish gangleader is the devil sitting on the shoulder and whispering into the ear of a young man (played by Loren Dean) drawn into the glamorous world of Thirties mobsters and the molls who love them. "You're my prodigy!" he tells the innocent, right before the organized-crime figure offs his partner (Bruce Willis) and takes up with the man's wife (Nicole Kidman). Naturally, a life-threatening love triangle ensues. Hoffman is all coiled menace until he isn't; once he loses his cool, heads get bashed and bullets get fired. This feels like a dry run for the star's character in the HBO show Luck several decades down the line: A man who values loyalty, plays his cards very close to his chest and trusts no one.