1. 'Titanic' (1997)
What's that you say? You don't think this movie is all that? Tough. James Cameron's 1997 box-office record-breaker, Oscar winner, and all-around pop-cultural juggernaut was the most expensive movie of its time — not to mention a years-in-the-making, snidely-dismissed production that sometimes seemed like it would never see the light of day. Then it finally came out … and it was awe-inspiring. As a piece of filmmaking, it does for the vast darkness of the sea what David Lean's Lawrence of Arabia did for the sensuousness of the desert. It also presents a disaster movie extravaganza without ever losing its sense of tragedy (even as it indulges in state-of-the-art effects to show the devastation of the historic shipwreck).
And then there's Leo and Kate. Yes, the logline of their relationship – adventurous drifter falls for frustrated, upper class girl – is pure corn. But the two young stars infuse their earnest back-and-forth with so much genuine emotion that it's hard not to get swept up in their doomed love affair. It's still the highpoint of DiCaprio's career, and one of the greatest old-school movies to come out of Hollywood in the last 20 years.