This isn't a list of the "objectively best" films. It's not about technical achievement or cultural importance. These are the movies that shaped me, the ones I return to, the ones that taught me something about myself, the ones I can't imagine my life without.
10. Stand By Me
"I never had any friends later on like the ones I had when I was twelve. Jesus, does anyone?"
Growing up, my friend group was my brother and my friend Scott who lived across the street. The three of us were inseparable, at least until we got older, started dating, started working, and just... stopped talking. Not with a fight. Just with distance and time.
Stand By Me understands that. It's not really about four boys looking for a dead body. It's about the last summer before everything changes. It's about friendships that define you and then quietly fade away.
I'm at an age now where nostalgia hits hard. I've got stories about those early friendships that I want to tell. Some of those friends are gone now. And like Gordie, I find myself becoming the storyteller, the one who keeps the memory alive by writing it down.
The film also gave me my first taste of what I now call "dirty endings," stories where the heroes don't win clean, where loss is woven into the fabric of the narrative. The final title cards revealing what happened to each boy hit me harder than any twist ending ever could.
9. Clerks
"I'm not even supposed to be here today."
My friend PJ introduced me to Clerks when I was working as a cashier in a grocery store. The irony wasn't lost on me, watching a movie about retail hell while living retail reality. But here's the thing: I actually loved that job. I loved the customers, the conversations, the camaraderie with coworkers my age. We'd go out after work, shoot pool, drink too much. They were my young adult friend group.
What Clerks gave me wasn't commiseration, it was voice. Kevin Smith writes dialogue like people actually talk. Conversations about nothing that somehow mean everything. These weren't movie conversations; they were my conversations, the kind I'd been having my whole life.
And Dante? I was absolutely Dante. Trying to keep everyone happy except myself. Feeling trapped in a life I didn't choose while secretly believing I was meant for something more. Smith understood that particular flavor of Gen-X paralysis perfectly.
I still try to write dialogue the way Smith does. Real talk. Tangents. The philosophical debates that happen when you're just hanging out with your friends and the world feels small enough to figure out.
8. The Empire Strikes Back
"No. I am your father."
I need to be honest about why Empire is on this list. It's not because it's the best Star Wars film (though it is). It's not because of the twist (though that moment shattered my young brain). It's because of my dad.
We watched the original trilogy together on VHS, sitting on the living room floor. He passed away not long after. Empire isn't really a movie to me anymore. It's a time capsule. A memory of being a kid, before everything changed.
The revelation that Vader was Luke's father was world-shattering when I first saw it. Now, knowing how movies get made, it's lost some of that magic. But I still look at that moment with childlike eyes. I still feel the weight of a story that dared to end with the heroes in peril, with evil winning, with everything uncertain.
Empire taught me that stories don't have to wrap up clean. That's probably why I gravitate toward films that embrace complexity over comfort. I love dirty endings, and I think it started here.
7. Pulp Fiction
"Zed's dead, baby. Zed's dead."
Pulp Fiction broke my brain. I'd never seen storytelling like this before, non-linear narrative, protagonists who weren't good guys, an anthology of stories connected by threads that didn't fully resolve. It was my first exposure to the idea that movies could break the rules I didn't even know existed.
Like Clerks, it's the dialogue that hooks me. Tarantino writes conversations that feel like eavesdropping on real people, except those conversations can turn suddenly, violently wrong.
Here's the thing though: I never related to the cool characters. Not Vincent, not Jules, not Butch. I related to Jimmie, the guy in the bathrobe trying to deal with a problem before his wife gets home. Just a normal person caught in someone else's mess. That's the character that feels like me.
6. Sinners
"We don't run."
A 2025 film on my all-time list might seem like recency bias. It's not.
There are only a few times in my life where I've been pulled into a movie so completely that it felt like something beyond cinema. The barn scene in Sinners was one of those moments. I've watched it on repeat. There's something I genuinely believe, that powerful music can traverse time and space and bring us all together, and that scene captures it perfectly.
Ryan Coogler took the vampire genre and gave it fresh blood (pun intended) by using vampirism as a metaphor for cultural appropriation. But what drew me in more than anything was the portrayal of the Black American experience in the early 20th century South. The first half of this film is a history lesson delivered through masterful storytelling.
The music elevates everything. The tone, the setting, the characters, it all works in harmony. And the ending brought tears to my eyes. For someone whose relationship with mortality and what comes after has evolved over the years, seeing that kind of reunion visualized hit differently.
This is my movie of the year, and I'm confident it will hold its place on this list for decades.
5. Highlander
"There can be only one."
For a long time, this was my number one movie. And unlike any other film on this list, I didn't just watch Highlander. I lived it.
I would sit in my front yard and sword fight with a tree for hours. My alias on BBSs was "Highlander" or "Luther MacLeod." To this day, my main email account is "LutherMac," which most people assume is about computers, but it's actually shortened from Luther MacLeod. Even this website carries that DNA.
I wore my trench coat until it wasn't cool. I listened to Queen's "A Kind of Magic" album on repeat for years. "Who Wants to Live Forever" remains one of my top 10 songs of all time.
The film asks a fundamental question: would you want to be immortal if it meant watching everyone you love die? My answer, still, is yes. Not for power, for curiosity. I want to see the future. I want to witness the next several hundred years of music, television, movies, video games, books. I want to know where humanity goes. The only way to do that is to live long enough to see it.
The sequels are trash. The TV series was surprisingly good. But the original stands alone, a perfect artifact of 80s fantasy filmmaking that shaped who I became.
4. Free Enterprise
"I don't want to be the guy who peaked at 25."
Most people haven't heard of this movie. It's a low-budget 1998 indie about Star Trek-obsessed Gen-X men confronting adulthood, featuring William Shatner playing a fictionalized, messy version of himself.
I discovered it during my indie movie phase, renting everything I could find at Blockbuster. It grabbed me immediately because it was me. These were my friends, or at least, the friends I wanted to have. Hanging out, going to movies, playing games all night, having exactly the kind of conversations I'd been having my whole life.
I was much more a Trekkie than a Star Wars fan (still am), so the Trek obsession clicked. But it's deeper than that. The film is about men who haven't quite grown up, still clinging to their childhood passions while struggling with relationships and careers. When I first saw it, I was absolutely in that journey. Sometimes I still feel like I am.
Free Enterprise is the start of what I call the "personal" section of this list. From #4 up, these aren't just great films. They're films I wanted to live inside. Films that shaped what I want to create. I still follow Robert Meyer Burnett on YouTube, still dreaming the same dreams.
3. Chasing Amy
"I love you. And not in a friendly way, although I think we're great friends. And not in a misplaced affection, puppy-dog way, although I'm sure that's what you'll call it."
Kevin Smith's most emotionally raw film. A comic book artist falls for a woman, discovers she's a lesbian, somehow starts a relationship anyway, and then destroys it through his own jealousy and insecurity about her sexual past.
I've been Holden. That feeling of being out of place in a relationship, "why is this amazing woman with a shlub like me?", I know it intimately. The way he sabotages something good because he can't get out of his own head, can't let go of things that don't matter. I've done that. It almost cost me everything more than once.
The Silent Bob speech is the emotional core: he let his own hang-ups ruin a relationship with a woman, and now all he can do is try to stop someone else from making the same mistake. Holden takes the wrong lesson from it. He loses both his relationship and his best friend.
There's a scene where Holden finally confesses his love, and I can't tell you how many times in my life I've wanted to say those words to someone but couldn't. Fear of rejection. Fear of destroying a friendship that mattered more than a potential relationship. Chasing Amy understands that paralysis.
2. 500 Days of Summer
"This is a story of boy meets girl. But you should know up front, this is not a love story."
More than any other film on this list, I am Tom.
The Expectations vs. Reality scene, that split-screen showing what Tom hoped would happen versus what actually did, I've lived that moment so many times. Going into a situation expecting one thing, going home alone and sad.
But here's what a lot of people miss: Tom is wrong the entire movie. Summer tells him from the beginning that she doesn't want anything serious. He doesn't listen. He projects a fantasy onto her, and when reality doesn't match, he blames her. She's not the villain. He's the unreliable narrator of his own romantic failure.
I learned from Tom. There was someone in my life who told me straight up she didn't want anything serious. Unlike Tom, I kept it at that. I didn't push, didn't try to change her mind, even though I wanted to marry her more than anything. Eventually, she came to me. She said she loved me first. And that opened the door for me to share what I'd been holding back.
That's why this film is so high on my list. It's not just a movie I relate to. It's a movie that taught me something. The cynicism came before I saw it; I'd already learned not to believe in "happy forever after." But watching Tom's mistakes helped me not repeat them when it mattered most.
1. Eternal Sunshine of the Spotless Mind
"I can't see anything that I don't like about you." / "But you will."
A man discovers his ex-girlfriend has had him erased from her memory. He decides to do the same. But mid-procedure, as he watches his memories disappear, he realizes he doesn't want to forget her after all. He fights to hold on.
I love the story. I love the concept. I love the surreal visuals and the labyrinthine script. I love Jim Carrey and Kate Winslet giving performances that shouldn't work but absolutely do. I love the way it uses the sci-fi premise to tell the story non-linearly, to make us experience memory the way memory actually feels, fragmented, unreliable, precious.
But that's not why it's number one.
It's number one because it's about the question I've asked myself after every relationship that ended badly: if I could erase it, would I? And the film's answer, my answer, is no. The pain is worth keeping because it's part of who I am. The memories matter, even the ones that hurt.
"Meet me in Montauk." Joel fights to preserve one last moment, a point before everything went wrong. I understand that impulse. The desire to go back, to fix things, to start over with a clean slate.
But I've also learned what Joel learns: some relationships weren't meant to work, no matter which point you try to fix them from. You can wish you could go back, but even if you could, it would fall apart for another reason. Some people are just too different, with too different expectations out of life.
The ending is what elevates this above everything else. Joel and Clementine find each other again. They listen to tapes of everything they hated about each other. And they choose to try anyway. "Okay." "Okay." It's hopeful but clear-eyed. They might end up right back here. They know that. And they choose each other anyway.
That's love. Not the fantasy. The choice.
Honorable Mentions
Toy Story - The film that proved animation could be for everyone.
50/50 - One of the best films about facing mortality with humor and honesty.
Her - A quiet, devastating exploration of connection and loneliness in the digital age.