A Highly Comprehensive Analysis of Leonardo DiCaprio’s Greatest Film Works (AKA Tears)

Let’s be honest. This thing I have with Leonardo DiCaprio is an illness, more than anything.

My favorite actor, Leo has this personal aura and aesthetic that’s completely malleable to any time period, any geographical region, any economic class and any age. He can contort his face into the creepiest mask of disgust, and I still think he’s hot. An even greater testament to his attractiveness is the fact that he can be dressed in board shorts, a white t-shirt, full-beard, sucking on an e-cigarette, surrounded by VS Angels, and I still find him to be effortlessly cool and dreamy. Even at the stone-cold age of 39, he’s completely desirable to a dumb and average-looking (at best) 17 year old.

Among people my age, DiCaps is highly regarded for his excellent film work in Titanic (sounds sarcastic, but is blatantly serious) and his boyish charm as a slick-and-turtleneck wearing twenty-something American sweetheart:

And that’s totally great, because I love Young Leo, too. He deserves to be appreciated. He gave us great things to think about, like this meta quote:

“Being dubbed as a hunk sort of annoys me. It gives me a yucky feeling.”

We love Young Leo because of two sweet little flicks that changed the game: Titanic and Romeo + Juliet. The former must be viewed as a mandatory rite of passage for all teenage girls — if you can’t recite at least ONE line from Titanic, you might as well be dead to me. As long as you were born after, like, 1989 (maybe earlier, I can’t do math), you had the pleasure of watching the latter in your English class during the Shakespeare unit.

I’m going to go out of my way and personally thank both history and Willy Shakes for allowing Young Leo to die in film versions of your greatest works (okay, the RMS Titanic may not have been one of history’s “greatest works,” but you can shut up). You are a credit to society.

So, yeah, we’re all dying to die in the Atlantic ocean because of our boy Jack Dawson, and we’d probably drink poison if it meant taking our last dying breath next to the bloody and beaten Romeo Montague. But when will the majority of us teens (and I hate to generalize, so I’m strongly stressing majority here) watch some of Young Leo’s finest works?!

[DISCLAIMER: Basically everything Leonardo DiCaprio has ever done is considered a critical darling and is extremely well-received — this is including riding a Vespa, eating meals, and wearing masquerade masks. The films I’ll address in this post, I feel, should be more widely recognized by teenage fans who might not be aware of some of Leo’s earlier work/less popular stuff]

Take What’s Eating Gilbert Grape, for example. I’ve discussed this cinematic masterpiece with several people, and we all agree it’s great, but I feel like it’s nowhere near as appreciated as it should be my people my age. This is one of Young Leo’s most impressionable performances, because he plays a boy who’s mentally disabled, and even I ask myself every time I watch it, “Wow, what a talented disabled actor.”


But there’s nothing like a drugged Young Leo, and that’s why The Basketball Diaries sits fairly high on my list of favorite DiCapricorn (NOTE: Leonardo is a Scorpio. I just thought it would be a fun nickname for him when we’re dating) movies. I have this thing where I like my young actors playing roles that require them to be skinny, mean, and out-of-their-minds on drugs. Lil’ Leo passes my test with flying colors in this movie, and he has such range! The first time I watched The Basketball Diaries, I pretended I didn’t like it, then took the DVD up into my room and watched it two more times in a row.

You’ve unwittingly seen a clip from Marvin’s Room (not the Drake song, but the movie) if you’ve ever decided to become a hipster on your Tumblr or something:

Yeah. That GIF you reblogged to seem worldly and enriched by a Leonardo DiCaprio film clip that you probably assumed was from, like, some Titanic deleted scene, is actually from MARVIN’S ROOM.

I really adore this movie, and not just because it’s very hush-hush. Not many people have seen it in general, despite the fact that it was nominated for a slew of awards, and stars not only Young Leo, but also Meryl Streep, Diane Keaton, and Robert DeNiro. It’s one of the most heartbreaking scripts, and has all these emotional layers that are played so well by the cast.

One reason I love Marvin’s Room is because Caps (another potential pet name) plays the quintessential teenager. Okay, so he burns down a house and has to be strapped down in a mental institution, but some of his mean quips and rude behavior have really inspired me. He’s so quick and sharp-tongued! Truly a model for us all. He even nails the awkward extended family hug.

There’s also Total Eclipsewhich isn’t even that great, but which I chose to include because there’s some crazy shit going on in this movie, and it’s really entertaining in a ridiculous way. Young Leo plays Arthur Rimbaud, and at the end he’s dying in the desert with a mustache, and he looks like the handsomest little sickly gentlemen.

I love a good mustache

Total Eclipse also spawned a widely-known, Tumblr famous GIF:

Here is where we begin transitioning into Middle Leo, which isn’t quite Young Leo, but certainly isn’t Old Leo. As far as I’m concerned, Leonardo DiCaprio is still very much Middle Leo. He isn’t old, guys! He is still youthful, and his eyes have grown even more crystalline with age!

Let’s go over Catch Me If You Can. This is probably my second favorite movie, if not first (in competition against another Middle Leo movie). It was around this time that DiCapriSun (another creative couple-y nickname) started doing more “biopic”-ish roles. He plays Frank Abagnale Jr., a 16-year-old con-artist who successfully posed as a pilot, a doctor, and a lawyer. It’s one of his best performances, and it still makes me angry that he didn’t get the notoriety he deserved for this. HE WAS PLAYING A CHARACTER 12 YEARS HIS JUNIOR.

When I’m being completely honest with myself, The Aviator is not only my favorite Leo movie, but my favorite movie OF ALL TIME. I’ve seen this movie upwards of 10 times, and it never gets old. There’s a certain form of artistry and dedication that Leo brings to this performance. He captures the era in such a realistic and touchstone way, and he, again, paints such a tortured yet uplifting face of mental disability with his role as Howard Hughes (who apparently is not famous among teens??? WTF!). The Aviator is movie-making magic at its most visceral, its most intense, and that can be accredited to both Leonardo’s fascination with the character, as well as Martin Scorsese’s filmmaking technique. The colors are so rich, the script is so exciting and intriguing, and the score is a true, sweeping testament to the 1930’s.

There are times in this movie that Leonardo does not look perfect:

But it kind of just makes the film even better. It’s because Leonardo DiCaprio, while ridiculously handsome, doesn’t have to rely on his outer appearance to give a movie meaning. He can seriously act. It’s insane and incredibly fun to watch.

He also has some good-looking scenes, but they’re far outweighed by the talent he brings in all the other OCD, bloody, naked, bearded scenes:

This is hot to me, you mouth-breathers

Leo really hit his stride after The Aviator, making AMAZING flicks such as Revolutionary Road, Inception, The Departed, Blood Diamond, Django Unchained and The Great Gatsby. But these movies (maybe aside from Revolutionary Road) are well-known by people my age, especially Gatsby, because it’s on every damn high school syllabus in Western society.

But if you’re really looking to treat yourself with a modern Leo film (but only after watching ALL of the above movies), may I highly recommend The Wolf of Wall Street.

This movie is a triumph (do I sound like a Rolling Stone film critic yet?). Again, the pairing of DiCaprio and Scorsese hits it out of the park. From the colors, to the music, to the script, to the insanity, it’s all done in such an organized chaos. It will be the perfect cap on a week-long Leo marathon. People have those, right? Not just me?

Loving Leonardo DiCaprio is not a choice — it’s a lifestyle. I know you want to only see him as a lovestruck teen, but go for the grit! He’s an intense actor and us teens should give him a fan base that extends far beyond the movies teens were heralding him for in the NINETIES!

Leonardo DiCaprio is one of few people I would give my kidney to. I also think we would make a great team, whether it be in business, in friendship, or in love. I have some great qualities — for one, I am my doctor’s favorite hypochondriac. I also eat a lot of pizza. I will sweat more than Leo in a hot yoga class, and I will donate my entire life savings to his environmental causes. I spend my weekends alone. We have so much in common!

So, fire up your favorite Leo D movie this weekend, whether it be Titanic or Don’s Plum (just kidding — you can only watch Don’s Plum on YouTube, and no one has the time for an almost 2 hour movie that was COMPLETELY IMPROVISED. Not one of your bests, my Italian friend). Because today, we salute a true American hero. Thank you, Leonardo DiCaprio. Thank you forever.


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