The Top Ten Movies That Made Stew Cry

Good fiction makes me cry, man. I’ve never hidden this fact.

If something is well-made and has basically any amount of emotionality to it, I will likely shed a tear or two. Usually not much, but make no mistake… there are movies on this list that made me sob. Just full-on ugly cry. I think part of my brain appreciates writing that is able to hit someone’s emotional core. I swear, sometimes I cry not because the subject material is so sad, but because the writing is so brilliant; I’m almost shedding tears in celebration of the art of it all.

So yeah… I’m both a sucker AND a sap.

With that in mind, let’s get into this one right away. It’s the Top Ten Movies That Made Me Cry (at least a little).

10. Chasing Amy

Okay, okay, okay. Hold on. Hold on! I will explain! Kevin Smith’s third movie was likely highly emotional and impactful for HIM, but for the rest of us, it’s a vulgar little comedy about sex and sexuality jokes that probably hasn’t aged super well AT ALL if I were to watch it in 2023. But making someone CRY?

Well, there is one moment. It’s the second to last scene of the movie, the beginning of the epilogue, and it sees Holden and Banky interact from a distance at a comic book convention one year after the last time they spoke to each other. As Banky entertains a fan, he and Holden have an unspoken communication across the floor. And as Holden walks away to talk to his ex-girlfriend, Banky watches him go and utters a final, “Yeah… bye” to his former best friend, whom he will never see again.

For background, I saw this in college, about six or seven years after it came out. I had moved into college, and all my high school friends had moved varying distances away. I hadn’t had a quality interaction with them in quite some time, and I was realizing a phase of my life was over. (There’s even more to it than that; I wasn’t doing particularly well at all in life in my early 20’s, but that’s just connective tissue here)

Anyway, Jason Lee’s delivery just hit me in a sore spot at the time–missing all the people who meant the world to me for my entire life to that point–and yeah. I cried. I’ll own it. Weird movie to cry at, but… here we are,

9. A Man Called Otto

Jesus, this movie. NOT a weird movie to cry at. Not at all. A Man Called Otto is borderline emotional torture porn. And it NEVER ENDS. Every time you think the flick has turned a corner and is going to move forward with Otto’s current life, you get ANOTHER suicide attempt and ANOTHER flashback to what made him the broken, bitter man he is.

A paralyzed wife who ended up getting sick and dying. A child who died in the womb during a tragedy. It just keeps coming at you, and you are well into the third act before the flick starts really getting anything resembling optimistic.

My wife just sobbed the entire duration of this flick in the theater. And I cried a good chunk, too, even though it’s all just emotional manipulation. The worst kind of crying! It’s not well-done; it’s borderline abuse. But it worked.

8. Into The Spider-Verse

“I’ll miss him”. Those three words, spoken by Stan Lee, in a movie that released shortly after his death. He spoke about the dead Peter Parker in the context of the movie, but to me? He was speaking for all of us, about himself.

Not big tears. Probably just one. But those three words meant so, so much at the time.

7. 50/50

It’s about a young person getting a cancer diagnosis with the titular prospects of surviving. Of course it gets sad!

On the way there, though, this is a wonderfully charming drama-comedy starring Joseph Gordon-Levitt and a revelatory performance by Seth Rogen (this was the first movie I ever did not actively dislike him) as a pair of lifelong buddies coming to terms with events neither of them should have to.

The heaviest moments start late when Gordon-Levitt just owns a scene where his character finally gives into all of his suppressed fear and rage and sadness, and he just flips out of Rogen for not being dependable when JGL needs him most. He screams and rages and melts down. From there, the movie just moves on to, oh you know, this character going into surgery and maybe dying from his disease.

6. Muppets’ Christmas Carol

This is where “appreciating the art” kicks in, because there is NO REASON to shed any tears at this flick. Everyone knows how A Christmas Carol ends; you know it works out for everyone for the best. AND YET!

This story is so unimpeachably told and acted and shot, that when you are with Scrooge and The Ghost Of Christmas Future seeing a world without Tiny Tim… god damn, man. It gets you, it really does. It hurts seeing Kermit and Ms. Piggy living in their dire straits, without their youngest child, and still trying to make the best of what they have.

I’m not a big believer of “At Christmas, you watch [X]”, but if I were? This would be my every year Christmas movie.

5. Eternal Sunshine Of The Spotless Mind

Here it’s Joel’s late realization that he doesn’t want to lose his memories, and his mad dash through his own mind as he struggles to hide, fight for, and beg for the retention of the good times he shared with Clementine. It’s the ultimate break-up movie in that regard. If you could, would you erase your ex from your brain? Would it be worth losing the memories of what made you happy?

I haven’t seen this since I was in my 20’s, and now that I’m living a pretty happy life with my excellent wife, I probably wouldn’t cry much at this one. But once upon a time, this was in my top five favorite movies even though it could be such a hard watch when you are 26 or so and reflecting on all of your failed relationships!

4. Everything Everywhere All At Once

This is particularly weird one because I saw it twice, and I did NOT cry the first time I saw it. So why should I cry the second time when I knew how everything worked out?

I have no real explanation. But the second time, it started with Waymond’s ceaseless positivity, and his imploring with Evelyn that there has to be a better alternative to fighting. I think hopefulness can really get to me sometimes. Perhaps the first time, I was just too entranced by the movie to really grasp his attitude. The second time I could focus more on Ke Huy Quan’s performance and get tangled up in it.

From that moment, a lot of the rest of it got me. Evelyn and Joy’s relationship outside the laundromat. The alternate universe where Everlyn and Waymond missed out on being together. Once this one kicked me in the heart, it just kept attacking. Such an amazingly good movie.

3. Up

So, storytime: My wife and I rented this from Redbox (YES, REDBOX! Remember that?) several years ago and sat down to watch it. We got about 15 to 20 minutes in, and our power went out.

We were both red-faced crying and asked each other “Do we ever want to finish this movie?”. Eventually, after going out for dinner until our power came back, we did decide to wrap it up. And hey, good decision. It’s a really good movie.

But that opening, damn.

I’ve since said that A Man Called Otto is the first 15 minutes of Up stretched out to a feature length film, by the way.

2. The Iron Giant

“Superman”.

That was it. Just that word. DEVASTATED ME. Are you kidding me, movie?

1. Your Name.

Hahaha, oh man, I pretty much ugly cried my way through the whole third act here. The story is just so damn potent, and the characters are so lovable. When you hit the reveal of what is going on between Taki and Mitsuha, I was fascinated, and as the two try to find each other… man, everything just hit me dead center.

I watched this a second time with my wife, and I STILL cried, but less so because I am a big strong man who knew what was coming. My wife… did not cry at all. Whoof. That was a shot to the old ego.

But whatever. I just think this whole movie is beautiful. The story, the animation, the heart. It’s amazing.

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All right, it’s time for me to dry my eyes, because that’s my list. But now it’s your turn:

WHAT MOVIES MAKE/MADE YOU CRY?

Let us know in the comments!

Until next time… take care!