In  honor of  the new Horror/Thriller Shutter Island  coming out today I  thought I would do a Top Ten List of Martin Scorsese  pictures.  Then I  realized that three years ago I   already made one. So, I decided to make a the list of best Leonardo   DiCaprio movies instead.(Judging the movie, not the  performance, which would be a different list.)
Leo's had an  interesting career.1   After some early TV work as a kid  (including the infamous Growing Pains  role), DiCaprio came to  prominence with an unexpected Oscar nomination  as a retarded boy in What's  Eating Gilbert Grape? Then it was  teen angst films, until a little  something I like to call Titanic  came around, and Leo-Mania  ensued. 
The Leo  backlash was  predictable and intense, fueled mostly - I believe - by  the fact that so  many (myself included) were DEEPLY uncomfortable  holding any allegiance  or admiration to someone worshiped by white  girls everywhere.  Leo kept  plugging away, and upon finding Scorsese  for their first (of 4 so far  with #5 in the works) collaboration Gangs  of New York. 
From that point Leo's star started to rise steadily again. More Award nominations, Box-Office Muscle, and respect of peers and the general public until you got to 2006, when it became clear - even if still painful to admit - that any serious discussion of Best Actors Under 40 simply HAD to include Leo in the Top 5, if not at the apex. (I've done this list before, informally, but it's out of date; someone remind me - we WILL do it again.2)
Leo had  arrived, and it was cool to  like him again.3
1 Leo's career path reminds me of Justin Timberlake. Initially N*SYNC was the best of the "boy bands," and you'd even bob your head in the car to "Bye Bye Bye" (or if no one was looking, do that puppet-dance thing). But actually LIKE N*SYNC? Not if you were a guy, or a girl over 22. When Timberlake hooked up with Britney it seemed all over. But then they broke up, he wrote the scathing "Cry Me a River," unabashedly emulated MJ's sound, produced some pretty decent pop songs, and started banging every smoking hot chick he could find. He even killed as a SNL Host. Suddenly it was far more acceptable to be a Timberlake fan. Uh, not that I am. No, not at all....2 Both Matt Damon and Jon Hamm will fall from the Under-40 ranks in a few months, so the impetus is on. Thank the Light, we've still got some time for Freddie Prinze Jr.3 ...Although maybe not by everyone. A couple weeks ago I was talking to a friend of mine about her upcoming baby. She named him Leonardo DaVinci ____, to help inspire the child to greatness. The middle name was necessary, she claimed, "so the world will never be confused who he was really named after." I was too scared to ask whether her fear was that people would think her son was named after DiCaprio, or the Ninja Turtle. Personally I would be fine with the Teenage Terrapin being the namesake. After all, Leonardo did lead. You'd want to avoid Raphael, who was cool, but, if my sources can be believed, quite crude.
Below is the list  of Leo's Top Ten Films. Here is his IMDB Page,   in case you want to grouse over what I missed. True, I haven't seen a   few of them (covered below4), but I did the best I could. If   Shutter Island or any of the other  30 projects he's got in  development  end up any good, we can update the list later on. 
THE TOP TEN LEONARDO DICAPRIO MOVIES  
#10  Marvin's  Room -  I saw this movie 14 years ago  and my main memory is thinking  (then) that young Leo could handle  himself on screen with the likes of  Meryl Streep and Diane Keaton. Sign  of great things to come. 
#9  The  Man in the Iron Mask  -  Iron Mask came out  in March of '98, when  Titanic was still ruling the Box-Office, had  plundered the Oscars, and  Leo Mania was in full-bloom. I took my  sisters to see it, me wanting to  introduce them to a famous literary  work, them for....well, they were  young. Anyway, at one point a naked  male butt appeared on screen and my  youngest sister - already at the  breaking point with her love for all  things Leo - let out a scream like  a banshee at a Def Leppard concert. To this day I  don't know what  embarrasses her more: that she screamed out in a theater  like that, or  that she did so at the sight of Gerard Depardieu's bulbous pock-marked  ass. (I'd link to visual proof, but some things simply  cannot be unseen.)
 #8  Blood  Diamond -  Intellectually I was kinda  annoyed at how one-dimensional  they made a very complex issue, though I  enjoyed the movie for all that.  Then again, it's probably the only way   to get most people to even pay attention, so hard to complain. I will   say that DiCaprio NAILS the Rhodesia accent, which is much tougher than   you might expect. (And not for nothing, but Djimon  Hounsou absolutely goes in my "Top Ten List of Actors who would be  considered Crowe or Penn-level Good if only they were White." Someone  remind me, and I'll do the actual Top Ten next week.)
#7  Celebrity  -   An overlooked Woody Allen gem,  DiCaprio riffed on his then-image by  playing the bad-boy actor known  for banging models and trashing hotel  rooms. The site of Kenneth  Branagh (basically channeling the Woody  persona) in bed in an  accidental foursome with Leo was priceless. (Re-watching  this movie with what we know now, it's amazing we didn't see Charlize  Theron's potential greatness sooner. She is Ta-Dow!)
#6  Catch  Me If You Can -  Spielberg doesn't get  enough credit for how  wonderfully he captured the jet-set glamor of  Flight in the 1960s. Even I  remember when pilots were seen as heroes.  DiCaprio is wonderful here,  never a false moment of a genius kid  pretending to be an adult - but  painfully aware he's clomping around in  his dad's shoes. Christopher Walken earned a deserved Oscar nomination,  Tom Hanks was quietly brilliant, and Amy Adams foreshadowed her  ascension. 
#5  The Aviator  - This film is so perfectly made I  should be over the moon with it. I do  enjoy it, but maybe Hughes is a  hard subject to warm up to. Cate  Blanchett won an Oscar and Kate  Beckinsale (and even Gwen Stefani!) are  pitch-perfect, but Leo holds  every scene together. The 2002 double-bill  of great performances (along  with Catch Me) put Leo back in firm A-List Icon status, but it   was this performance, full of Hughes's charm and bravado but also his  crippling OCD, that made me realize we were looking at someone who   aspired to - and may hit - the Pantheon. 
#3 (tie)  Gangs  of New York  and  The  Departed - I could rank these two films five different times  and switch position every one of them. I noticed in my Scorsese ranking   that I had Departed ahead, but I'd just seen it.  Gangs  has  more flaws, but is also more epic in scope, and while Jack's  performance in Departed  diminishes a bit with repeated viewings,  Daniel Day-Lewis's Bill the Butcher only gets  better.  (Damon  was great, too, but DiCaprio shown. I know some will disagree, but for  my money, Departed  definitively showed that Leo is the  better actor, or at least has the  higher ceiling, and greater range.) 
#2  William Shakespeare's Romeo +  Juliet   -   I went back and forth on my top two more than a few  times wanting  to make this #1. Ultimately I realized I was A) picking my  favorite of  Leo's films over what is the best and B) unconsciously  afraid of the  backlash. Afraid? Me? Bring it on. But we'll get to that.  In its own  right, R+J is one of the most underrated movies of the  '90s, a  film that at the time was crushed by critics. They were just  scared,  seeing true Visionary Art as avant garde pretentiousness.  They  were wrong. I cannot tell you how great this movie is. The film is  by  Baz Luhrmann, who went on to make Moulin Rouge! next. (I  suppose  I either just made my case in one sentence, or turned you off  from R+J  forever. I'll live with that.) Luhrmann uses Shakespeare's dialogue  from the play, which had been done before (some time check out  Ian  McKellan's terrific Richard III), but never quite like this.  It  sounds so hokey, but the key decision (in my opinion) was to change the  gun names from Beretta and Colt to Dagger and Long-Sword. (And don't  even get me started on the Fishtank/Des'ree scene.  MAGIC.) Exquisitely  matching soundtrack to film in a way that put Luhrmann on  the Mount  Rushmore5 of Directors who know how to use Source  Music,6  Romeo + Juliet is a kaleidoscope of wonder,  heart-thumping  romance, and simmering lust. One of the most romantic  movies of all  time.7  There. I said it. Deal. 
And  the #1 Leonardo DiCaprio movie ever (so far)  is......
#1  Titanic  -   I can already feel the hate-mail  brewing, and all I have to say is,  it's time to come out of the closet,  people. Look, I get it. The  teenage girl/Leo thing was ridiculous, and  it made even the most  heterosexual man feel very uncomfortable. And  the movie was such a  Cultural Flag, you couldn't not talk about it in  the spring of '98. Our  society being what it is, it was only natural  that wave after wave of  protest would lap at the hull of Titanic's  popularity. (I  just realized that with a little moxie I  could make 10 more groaningly  bad boat puns before I'm done, and since  the next end-note already  subjects you to my oddball sense of humor, I  promise to stop now. You owe me.) 
Titanic  was everywhere. James Cameron was everywhere. Jack and Rose were   everywhere. Leo Mania was everywhere. THAT DAMNED SONG was everywhere,   and along with it, Celine Dion became a permanent fixture in our lives   for the next decade. It was all too much. I get it. I really do. But   that does not change the fact that Titanic was one helluva great  movie.  Disaster movies are tough to pull off.  They usually fail. Ship  movies  are tough to pull off.  Cheesy Romances are tough as nails to  pull off.  You put all three together? James Cameron had to make us  simultaneously  believe the boat was actually sinking, that 2000 people  were in danger of dying, care about them,  freeze right along with them,  all while caring about the fate of two  random people who really didn't  know much about anything. AND HE DID IT!  We've come to recognize Kate  Winslet as one of the best actresses  alive. Avatar forced us to  acknowledge Cameron is worth the hype:  he really is the King of this  world, and possibly others. We've even  forgiven and come around on Leo;  hence this list. But many people  haven't forgiven Titanic. You  know why? Besides all the reasons I  mentioned, you loved Titanic  initially. You did. You were swept up, maybe you  even cried a little.  Then you felt like part of the maddening crowd when  you realized every  other person on the planet had a similar experience.  So you rebelled.  You pretended you never liked it. You trashed the  actors, the director,  the dialogue - anything you could. But you know  and I know that deep  down inside you - your heart will go on.  And  that's okay. Put your  arms out and soar, baby: I won't let you fall. 
Hyperion
February  19, 2010
4 Leo Movies I have not seen - Haven't yet traveled with Kate and Leo in Revolutionary Road, but no one has been falling all over themselves with praise. This writer's eyes haven't seen Leo's first real movie, This Boy's Life, and can't find anyone who has, though by all accounts it is good. For some reason I have not digested What's Eating Gilbert Grape?, for which Leo got an Oscar nomination back in the day before becoming a household name. The Wikipedia plot account sounds absolutely ghastly, but I'm assured by Koz and Kaida that it's quite good - Kaida said it was the "feel good gigantic woman retarded boy house burning pool drowning face slapping movie of the year." Well then. I'd have to check my journal, but I'm pretty sure I have not seen The Basketball Diaries - though I did watch a lot of the Columbine coverage several years later, so I think I'm okay. Finally, I have not yet had a day with Leo at The Beach. For what it's worth, when I called Carlos to see if he had any insight on the movies I'd missed (or Leo in general), I found the Wolf-Cat in surprisingly eloquent form. Besides explaining the evolution of late '90s Boy-Bands to a "Doctoral Thesis-Defense" degree, Carlos had this to say: "Leo's best movie was Romeo + Juliet. His best character was the guy in Basketball Diaries. But his best performance, in my opinion, was in The Beach." All right, Wolf-Cat; now you got me curious.6 Source Music is previously-recorded music you put into a film - usually pop songs or classical pieces. They can be "in" the movie - like on the radio or TV, or part of the soundtrack. This is opposed to Score, which is composed directly for the film. (Think Star Wars.) Yes, I realize I put 6 before 5, but that's because 5 references Source Music so heavily that if you didn't already know what it was you'd have to go back and read the next footnote again. Who loves you? Who loves you? That's right: Uncle Hypey.5 The Mount Rushmore concept is pretty simple - four people (or fast food restaurants or TV shows or whatever the case may be) that define the very best of your subject. I would want to take some time to hash it out, but off the top of my head, my Mount Rushmore for Directors using Source Music would be Martin Scorsese, Quentin Tarantino, Baz Luhrmann and I was going to say John Hughes, but I just looked at his IMDB page, and though he had some all-time greats as far as Source Music goes, he only directed a few films, so we'll leave the fourth spot open, for now.7 I am absolutely going to have to write a review for Romeo + Juliet, as it deserves to take its rightful place among the movie gods. Maybe a running diary, with time-stamp cues so you can watch and read my comments at the appropriate time? I'm tempted.
Reviews for several of these films can be found at Movie Hype.
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