5. Wall Street
Despite a miscast Charlie Sheen as the co-lead, Wall Street, often perceived as minor Oliver Stone, is instead one of the director's best films (outside of his obvious masterpieces Platoon, JFK, and Nixon). A director who for over a decade had his finger on America's pulse, Stone is a true firebrand, and Wall Street, while not quite as scathing as the aforementioned triptych, is still a damning indictment of late-80s corporate greed. Starring Michael Douglas - on Oscar-winning form as the infamous Gordon Gekko - Wall Street gave birth to the line "greed, for lack of a better word, is good" (often cited wrongly as "greed is good", in a mistake similar to the "play it again, Sam" situation), and Douglas has never been better as the lizard-like Gekko, all braces and slicked back hair and motivational speeches and expensive whiskey in crystal tumblers. As in Platoon, where he was out-acted by that film's fantastic ensemble, Sheen is no match for it. But that's no matter, because Wall Street works in nearly every other regard, and the final scene, a showdown between the two stars in a rain-sodden park, remains one of Stone's great endings, with the greed winning, and not a dash of hope for goodness anywhere to be seen.