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Do you remember Walter Brennan? Sure you do. No? Well, you should. After all, he spent four decades as sidekick to some of the top stars in the business. If his face isn’t familiar, I’ll bet you’d recognize his voice. Like Cagney, Bogart, and Mr. Magoo, Brennan owned a voice that was unmistakable. It became fodder for comedians and impressionists, and I’m pretty sure one of your uncles took a crack at it, too.    Brennan was the go-to guy when a director needed a town drunk, a good-hearted hobo, a local priest, or a deputy (he was indeed a natural for Westerns). But to say he was merely adept at playing local yokels undermines his achievements in the business. Brennan won the first ever Best Supporting Actor Oscar in 1937, and by 1941 had won it twice more. His feat of winning three Academy Awards wasn’t matched by another actor until Jack Nicholson and Daniel Day-Lewis did it decades later (and Nicholson and Day-Lewis needed a lot more than four years to equal Brennan’s record). To date, Brennan is still the only actor to win three statuettes for Best Supporting Actor. 

The cinema has given us many great gangster films, showcasing some of the nastiest, shiftiest, most venal criminals in the world. On paper, their deeds are rotten, maybe even murderous, putting innocent people at risk and defying the forces of law and order.  Yet very often, you still sympathize with these characters; you may even root for them. After all, usually their backs are up against the wall. You sense that poverty and dysfunction placed them on the wrong side of society. Born into the right circumstances, they coulda been contenders. You glimpse a trace of honor, even goodness in them. Whenever there’s talk of the greatest films ever made, gangster pictures always figure in. You know the usual suspects, but we’ve rounded up ten of varying ages that we think are... well, for the ages.