5 Leonardo DiCaprio Movies that Make Guys Cry

DISCLAIMER: This is not a series dedicated to proving men shouldn’t cry, or to suggest ONLY women cry and are therefore inferior. The goal of this series is to dispel the pre-established (yet flawed) notion that being “manly” and being disconnected from your emotions go hand-in-hand. Even the most macho of men enjoy and even shed a tear at films, and the sooner we can admit that the sooner the concept that one sex is better than the other can go away. While the approach to these articles is one of light-hearted comedy, the emotional core is valid. While men might be more hesitant to admit it, movies often times have the potential to make us cry, for example:

“Leonardo DiCaprio Movies”

If you had told me around the time that Titanic came out that Leonardo DiCaprio would become a household name and all-around acting powerhouse, I would have thrown you against an iceberg in disbelief. But here we are, closing in on the Academy Awards and Leo might be closing in on his first Oscar. I have no icebergs to throw. Ok, that analogy has gotten cold. Ok, last one. Truth is, Leo has blessed Hollywood with a variety of awesome films, a surprising amount cater to both genders despite the emergent target audience of Titanic. He’s funny, suave, and has some acting chops that would make a dog drool. Ok, I’m going to stop with all analogies now. Here are five Leo films that hit guys in the feels, and yes, it’s ok for guys to like Titanic.

1. Inception
Let’s be clear here: The vast majority of this film’s content didn’t actually happen, even within the fictional reality of the movie world. That doesn’t stop us from caring about what happens, because of the excellent performance by Leo. He not only makes us pine for him to eventually see his children again, but make us jealous that he has Michael “Tangerine” Caine as a father-in-law. Even his suicidal-turned-homicidal wife is a tragedy for him to weather as he navigates a very complex plan to trick Cillian “Scarecrow” Murphy into making a business deal. The suspense is palpable, the music is iconic, and who doesn’t love a good Christopher Nolan movie? Leo does a fantastic job of working a thread of desperation into every step he takes, and I highly recommend it.

The ending is really tough, because of its implications. Ambiguously left, there are two options: Leo is still in a dream and he doesn’t care anymore, or he’s not in a dream and is actually with his kids. Naturally the second option is the happier, but the implication is that his wife ruined his life and killed herself for nothing. So yeah, no happy ending either way.

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2. What’s Eating Gilbert Grape
A common misconception for those who heard of this film but never seen it is that Leo is the titular Gilbert. In reality it’s our old pal Johnny Depp as the focus, with DiCaprio playing his mentally disabled little brother. This predated Titanic so it’s a real example of what Hollywood saw in this young actor. An engrossing film dealing with hard situations and difficult choices, it’s certainly not for everyone but it IS high quality. True, Depp takes most of the focus on this outing but the movie wouldn’t work without Leo bringing the goods.

I’m torn on what is harder to deal with emotionally in this movie but I’ll pick one part that stuck with me the longest. There’s a part where Leo is in a bath and Depp in true Depp fashion leaves to flirt with a girl, leaving Leo in the bath all night. The feeling in Depps stomach when he finds Leo in the morning, shivering and alone in the bath, is something that anyone who’s cared for anyone else would do anything to avoid.

3. The Aviator
Years later and Leo is still playing characters with mental health issues, but this time he gets to be rich at the same time. Howard Hughes, the real life inspiration for Howard Stark (you know, Iron Man’s father?) was a complicated man. He invented, flew, made movies, and waged an internal war for his sanity. DiCaprio shows all of that on screen with a mix of debonair smirk and vulnerable embarrassment that captivates any audience. You love to watch him when he’s at the top of his game so much that you feel betrayed when he relapses into depression and obsession. Then stupid Alec Baldwin has to step in and douche it up…get out of here Baldwin!

The most emotional part is late in the movie, but not quite the ending. Howard had locked himself in a screening room for months and did the whole “pee in milk jugs” ordeal. Then suddenly he emerges to defend his name and beat Baldwin and his political shills, as you do. Everything seems to be going great, and as everyone congratulates him, you think “Hey, maybe he’ll be alright”. Then he starts repeating the same phrase over and over again, getting more frightened and frustrated with each pass. We know that sheer will is not the cure he was hoping for, and that’s frightening for anyone.

4. The Departed

Headshots. Everyone gets headshots. You want to get shot in the head? Be in this movie, cause you’ll have a pretty high chance of getting shot in the head. I’m not sure what accuracy training these guys went through, but don’t let any storm troopers in to that class.

The Departed is about two men spying on the other’s organization. DiCaprio is a cop undercover with the mob run by Jack “The Joker” Nicholson, and Matt Damon is a mobster who’s undercover with the cops. At some point both men learn of the other’s existence, and the race to identify the mole begins. The quest to thwart the crime shenanigans of Nicholson almost seems a B plot when compared to the intensity of Damon and DiCaprio trying to figure each other out. And a ton of people get shot in the head, it’s pretty awesome.

Poor, poor DiCaprio. Remember, he’s a good cop undercover with the mob. Damon is revealed as a bad guy and DiCaprio captures him, only wanting to get his good name back and get paid. Instead, a dirty cop working for a now dead Nicholson, who himself was an FBI informant, shoots DiCaprio in the head. It’s abrupt and leaves no room for DiCaprio to get any sort of resolution. Boo to you, Damon. Go back to Mars.

5. Catch Me if You Can

This movie may have been based on a real life story, but it’s plot sounds like it was written for DiCaprio. A man is so suave that he can lie and con his way into getting whatever he wants. In a time before many of the higher-tech security features we have now, he would fake checks and identifications until he got whatever goods he was aiming for. Tom Hanks was the cop chasing him, and their relationship was so closely intertwined that DiCaprio’s character calls Hanks on Christmas to apologize for tricking him, but also because DiCaprio had no one else to talk to. In the end, DiCaprio is caught but was so good at what he did the FBI paid him to help identify fraud and protect against it. Pretty nice story and fun movie to boot.

The Christmas phone call is tough, but what really breaks DiCaprio and the audience is when Leo goes to his family home. He finds his mother with the man she left Leo’s father for, and a half sister. This other man represents a better husband than Leo’s father, the man Leo built his identity around. Having his mother there with a half sister was basically saying “Your father was crap and I found a better man. Since you’re just like your father, I now have a better child than you as well.” No wonder Leo turned himself in after that gut punch.

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Daniel Epstein
Father, filmmaker, and writer. Once he won an Emmy, but it wasn't for being a father or writing.