-- Clint Eastwood
Call me a child of the 90's, but this trendy retelling was about the only exposure a lot of us got to Shakespeare. The modernizing of the settings and visuals without touching any of the dialogue was hardly a unique idea, but the aiming of the movie squarely at the MTV demographic was a pretty bold choice. Between this, Titanic, and The Beach, Leo dug himself quite a hole at the beginning of his career that he had to climb out of to avoid being typecast, but as a standalone movie, it's still pretty good.
In my pantheon of depressing movies about relationships (along with Blue Valentine and Legends of the Fall, as the medal winners and Eternal Sunshine of the Spotless Mind if we're extending it to a Mt. Rushmore), I feel truly sorry for anyone who went into this thinking, given its two stars, that it was a thematic sequel to Titanic. Instead, it's more like if Jack lived, but he and Rose grew to hate each other over the ensuing years. Just tragic all around because of how flawed and real the characters feel as their relationship crumbles, you should probably avoid this one if you're a hopeless romantic; it'd just be too depressing.
Say what you will about its admittedly contrived and somewhat cliché - at this point in Hollywood, a twist is almost expected - ending (personally, I'd say it's the weakest of the Scorsese/DiCaprio collaborations), but it's still a fantastically entertaining movie. It's not quite as clever as it thinks it is, but you won't see the exact nature of the twist coming. Since it's Scorsese directing, you know the cast won't have a weak link in the supporting ranks, so their performances and his direction ultimately prop up a just above average script.
A biopic where DiCaprio played Howard Hughes, it should have won him the Oscar for Best Actor instead of just getting him a nomination (combined with his snub two years later for Blood Diamond makes me think the Academy will give it to him for The Wolf of Wall Street, almost as a cumulative award), but is still a fantastic film. Though it spans over a decade, Scorsese never lets the massive timeframe get unwieldy, and DiCaprio certainly has no trouble hitting all the points needed in Hughes's progression into something of a headcase.
Taking these kinds of chances is why Leonardo DiCaprio is one of my favorite actors. Playing a horrendously racist plantation owner was merely the culmination of Leo showing he could play a-holes; a journey that began with The Departed several years earlier. Fun fact: Will Smith turned down Jamie Foxx's role, citing a need to "play the lead." Apparently, (spoiler alert!) Christoph Waltz's character being the one to shoot DiCaprio's plantation owner made him the lead in Smith's mind. He would go on to make After Earth, an absolutely awful movie (but once you saw it was directed by M. Night Shyamalan, you didn't need me to tell you that) that was a starring vehicle for his son. His principles apparently can't hold out against nepotism.
This one is Daniel Day Lewis's movie, no doubt. The rest of the actors are just trying to keep up. Leonardo DiCaprio does a decent enough job, and if Cameron Diaz could've even hung in the race, this movie would've placed much higher. The film does a fantastic job of not prettying up its time period. The grime and general filthiness of the movie is pervasive, and you feel like you need a shower when it's over.
DiCaprio absolutely nails one of the toughest accents in the world to imitate: South African. A relatively by-the-numbers movie-with-a-message, it is nonetheless elevated by its performances and storytelling. Forget the hack reviews who couldn't wait to call it a "gem" or a "diamond in the rough" and evaluate the movie on its own. It has more to say than a first glance might tell you. Not that you'll feel particularly good about your next diamond purchase, but it's more than an infomercial designed to put you off jewelry.
Covered extensively in a review, this is the movie that would be #1 if we were ranking his movies based solely on the quality of his performance.
The Departed is the most memorable, well-acted crime movie since Heat, and that's high praise. Start to finish, you know there is no way this movie can end happily for everyone you want it to, but it's fairly obvious that it's going to be entertaining either way. With an absolutely loaded cast, DiCaprio doesn't have to do all the heavy lifting. In fact, the most memorable line probably comes from Mark Wahlberg, who says, "I'm the guy who does his job! You must be the other guy." Feel free to disagree with me on the best line as this movie is absolutely loaded with one-liners.
The perfect melding of leading man, director and premise (I always appreciate when Hollywood throws money at an idea that simply cannot spawn a sequel, although I can't put it past Hollywood, and most of the cast is technically signed on for them should they be made), Inception is specific enough to tell an amazing story, and vague enough that you might change your opinion on what that story is with each viewing. With 4 wins and 4 more nominations, it even appealed to the notoriously sci-fi averse Academy. Entire websites are built around competing theories of what's happening, with notables including "Cobb's wedding ring is his totem, not the top", and "we never see reality in the movie, only the first layer of a dream designed by Cobb's associates to help him get over his wife's suicide." Heavy stuff.
Ranking just behind "That Time Leo Accidentally Turned On His Phone's Camera" in terms of movie quality, J. Edgar is an ambling, directionless movie that because it follows J. Edgar Hoover at different points in his life, allows us to see what Leonardo DiCaprio will look like when he gets older... if he uses terrible makeup when he gets older. I understand why, on paper, "biopic of an American historical figure directed by Clint Eastwood" attracted DiCaprio to the role, but had he and Eastwood been anything less than Hollywood titans at the time of its release, this could have sunk their careers.