15 movies every man should watch as often as possible

Everyone loves a good movie night. Whether you like to get dressed and head to the theater so you can justify the biggest bucket of popcorn and soda you can find for something new, or you are the kind of guy who likes to lie out on the couch for an old faithful, we all love to sit down and allow escapism to take us somewhere more digestible than the real world. Some movies are meant to inspire; others are meant to frighten. There are good bang, bang, shoot ’em ups, roaring comedies, and everything in between. However, movies are also the best teaching tools if you know how to pull the right themes and ideas while watching. Now, this doesn’t mean you can get all you need to know from movies, but they are a great jumping-off point for learning some style, solving problems, or navigating adversity. This isn’t like every other movie ranking; this one has a specific purpose.

There are thousands of movies in every category below to choose from, and curating your own go-to list will help you elevate your life on your own terms, but here are 15 movies every man should watch soon and often.

3 movies to inspire you

Inspiration can be hard to come by. But movies have a particular ability to give you goosebumps. To light a fire you thought was snuffed out. These are three movies you should watch any time you need a little pick-me-up.

Rocky

There are few movies that would and should end up at the top of a list like this than the Sylvester Stallone epic, Rocky. We all likely know the premise of the underdog getting his shot and capitalizing on it. But the underlying theme of this movie that we can all take from it is perseverance. This is a movie about a man faced with endless roadblocks. And he kept moving forward. He never lets anyone tell him he can’t do it. And the result is the capturing of a dream.

Remember the Titans

Make a list of movies that will make every man cry like a baby, and this one will be near the top of the pile. Is this Denzel Washington’s best performance? That is kind of like picking the highest caliber Ferrari; there isn’t a bad one. But this flick, following the desegregation of a high school football team trying to navigate social and athletic problems at the same time, will forever be on the Mount Rushmore of great sports movies.

I don’t care if you like each other or not, but you will respect each other. And maybe… maybe we’ll learn to play this game like men.

Respect is free. We have become a nation of people who have lost the ability to disagree with respect. On a rewatch through the lens of today, it is easy to think of their racial differences and apply them to our political divide. And see the game of football as a metaphor for the game of life. What Coach Boone did with these kids was nothing short of a miracle, one we could use again today.

Good Will Hunting

This is one of the greatest movies of all time. This isn’t a question. This is a statement. When I got the opportunity to interview Matt Damon last month, he talked about this movie and how it changed a lot of people’s lives. It touched me at the right time as well. As someone who grew up with an alcoholic father, seeing someone on screen struggling with their childhood made me feel less alone. That would be enough if that was all this movie brought. But there is more.

The best day of my life is about ten seconds when I walk up to the curb and think that I’m gonna knock on your door and you’re not gonna be there. … No goodbye, no see you later, no nothin’. You’re just gonna be gone.

The most underrated part of this movie, and something we need to talk about, is the above quote. There are about a thousand quotes to pull from in any Robin Williams movie, which is probably why this quote gets overlooked. But this moment, where Ben Affleck calls Matt Damon to the carpet for wasting his gift, is the moment I learned what true friendship was about. His biggest dream was his best friend leaving him behind. He championed his success, even if it meant losing his most valued friendship. Every man should know what it is like to have a friend like that.

3 movies to define your masculinity

How do you define masculinity? If you spend too much time on TikTok, you will have a hard time not getting really frustrated with that conversation because it seems to be a dark hole of pessimism at the moment. But there are movies around, if you look hard enough, and find underlying themes that will teach you the true meaning of masculinity.

The Gentleman

Top five movie of all time for me. Partially because I love Guy Ritchie and his incredible ability to use a very specific c-word in virtually every conceivable meaning. But also because this movie has one of the best wardrobes in the industry. You can even learn a great dress code lesson from this movie, and that will always scratch my nerd itch. But there is a lesson in masculinity from an unlikely source that creates a stellar role model for young men while stealing the show as well.

My boys, they’re naive, they’ve had hard lives and they’re just starting to come good. But, they’re my lads, my responsibility, so it’s me that should be accountable for their actions. Now, I can return your goods, but I can’t return the inconvenience, the time, the fucking headache. And so I offer you my loyalty, my word, my time until that debt is settled. I’ll make amends, but just leave me lads alone.

Colin Ferrell’s character, Coach, takes in young men who are on the wrong path and corrects them. He gives them a purpose. Boxing becomes their passion and their teacher. But that doesn’t mean they go off without any issues. When four of his men do something stupid and dangerous, he steps up. He shows everyone the value of accountability. He takes responsibility for the people within his sphere of influence. That is the first sign of masculinity.

12 Angry Men

This may be the only movie on this list that one would call an “old classic.” Rocky is a classic, and so are a few others that are going to follow. But 12 Angry Men is the classic in the way that it came before color, and starred a legend the likes of Henry Fonda. Following a man who enters a jury deliberation room with 11 people who know for a fact the accused is guilty. He then stands up to them and, through all the ridicule, convinces them that it isn’t that simple.

It takes a great deal of courage to stand alone even if you believe in something very strongly.

Standing up in the face of adversity is one of the most difficult things to do in life. Standing alone for a cause you believe in while the rest of the world rages against you takes the kind of courage that could only be labeled as masculinity. When you are in a position where you know what you stand for is right and people push you to move, Henry Fonda teaches us to stare back and boldly say, “No, you move.”

Gladiator

As masculine as it gets. Gladiator is one of the movies that most men would declare as a rite of passage for young men to experience. It won Best Picture and launched Russell Crowe into superstardom. Maximus is one of the world’s greatest film characters, and he taught us something very valuable that we can still pull from this movie nearly thirty years later: Duty.

Sometimes I do what I want to do. The rest of the time, I do what I have to.

Cicero (Tommy Flannigan) is a supremely underrated character. While this movie has some epic moments, there is one cleanly delivered line that goes missed by so many. When Maximus asks him if he finds it hard to do his duty sometimes, he responds with the above. How often do we neglect what we have to do because we focus on what we want to do? The mark of a man is following true to his word and doing his job with pride. Sometimes you get to do what you want; enjoy those times. The rest of the time, buckle in and do what you have to.

3 movies to elevate your style

I mean, I am a style guy, and I write about style in movies a fair amount. And while I may be a massive James Bond nerd, I did my best to find three movies that will elevate your style without leaning so hard on 007. Look, it was hard, so listen to me when I say these are the best alternatives to Bond.

Once Upon a Time in Hollywood

I am hit and miss on Quentin Tarantino. I know, take my film bro card away. The truth is, I don’t think that anyone does dialogue better than he does. But of all of his movies, Django Unchained and Once Upon a Time in Hollywood are the only ones I can watch over and over. Maybe I just like Leonardo DiCaprio. And teaming him with Brad Pitt will never hurt.

When you come to the end of the line, with a buddy who is more than a brother and a little less than a wife, getting blind drunk together is really the only way to say farewell.

Casual cool is hard to pull off. But Leo’s leather jackets and Brad Pitt’s t-shirt and jeans (and don’t forget his stellar denim) will elevate your wardrobe for the off-duty times. Finding vintage upgrades from brands like Lucky, John Varvatos, and Guess will have you feeling old-school Hollywood.

The Talented Mr. Ripley

Is this my first repeat? My second Matt Damon movie. Oddly enough, my favorite Matt Damon movie isn’t even on this list. Mostly because there isn’t a lot to learn from The Departed. Other than that Jack Nicholson has a dreadful Boston accent. One thing this movie does do is shine a light on the dangers of toxic obsession. Envy is a powerful drug and can make people do the worst things imaginable.

No matter what you do, no matter how awful, no-one ever thinks that they’re a bad person.

How will this movie elevate your style? By injecting some mid-century JFK resort wear and nautical inspiration into it. Camp collars and boat shoes, short shorts and colors of the ocean. Sure, it may be a bit preppy and high-brow, but that is the point. It is the sign of luxury and elegance, the kind that someone like Ripley will kill for. Spoiler alert.

Wall Street

You know what I learned from this movie? Greed is good. But that isn’t why you should watch Michael Douglas chew up the screen in this film. Maybe you could watch it for the Daryl Hannah of it all. Or perhaps you yearn to see Charlie Sheen back when he was young and talented, not old and bat-shit-banana-camels. Or, if you’re like me, you can watch it for the really amazing 80s style that you can still rock today.

The main thing about money, Bud, is that it makes you do things you don’t want to do.

Pinstripes, contrasted collars and cuffs, braces, and wide lapels are the makings of a power suit. The kind of look that screams authority and wealth. If you were a man in the 80s wearing this, you were the king of the world, the head of the class, the talk of the town. Luckily for you, the return of the power suit means you can do it again. Only better. And without the greed…

3 action films to get you pumped

The alpha male. The dude’s dude. That is what you get when you put a muscle-bound martial arts expert in the mix against a slew of bad guys. But there is no Chuck Norris here. No Jean Claude Van Damm. These are some of the best action movies of the last forty years that will actually teach you a little something about being a man.

Die Hard

This is my favorite Christmas movie. I said it. Fight me. This was the movie that put Bruce Willis on the map. It changed what we thought of as an action hero. Before this, it was Arnold. It was Sly. It was Chuck. Bruce Willis came in here as the everyman, the guy who was just the fly in the ointment, the monkey in the wrench, the pain in the ass. And therein lies the lesson, actually.

Only John can drive somebody that crazy.

Before he commences to kicking ass for 90 minutes, John McClain (Willis) shows up to spend the holiday with his wife and kid. His life is a bit of a mess. It is actually quite sad before Hans Gruber shows up and takes the building hostage. So, when his wife sees a terrorist losing his temper, and she utters this line, it tells something about him. In the midst of everything going wrong in his life, John McClain won’t back down from something he is good at. At the end of the day, he is a hero and will always step up. He teaches us to never let circumstances keep us from doing what is right. Despite the odds.

John Wick

Keanu Reeves is not the best of the best when it comes to acting on screen. I think it isn’t a controversial thing to say he isn’t even a good actor. And yet, somehow, he puts out some absolute bangers in his career. John Wick is his only legacy character, and we waited until he was in his fifties to give us what we waited for his whole career. Expert technique both with a firearm and hand-to-hand, the kind of technique that cannot be faked.

I lost everything. Until that dog arrived on my doorstep… A final gift from my wife… In that moment, I received some semblance of hope… an opportunity to grieve unalone… And your son… took that from me.

So what can an ultra-violent movie about revenge teach us about being men? Well, look deeper than that (although it is awesome), and you will find the core of John Wick. He wasn’t successful because he was better than everyone around him. Sure, that helped, but he was victorious over and over because, as his enemies say, he is the embodiment of sheer force of will. He never quit. You couldn’t stop him. One thing I have learned in life, and in the writing business, success is less about talent and more about tenacity. Never quit on what you want.

Speed

My second (and last, I think) repeat on this list. Keanu does it again. While he could be on here for The Matrix, Speed is on here for a very specific reason. But first, we have to talk about Keanu with a shaved head, Jeff Daniels playing a SWAT officer, and the unavoidable crush we all had (have?) on Sandra Bullock. All three of these alone are reasons to watch this movie, but there is a lesson shining through for every man to take home.

It’s a game. If he gets the money, he wins. If the bus blows up, he wins. (What if you win?) Then tomorrow we’ll play another one.

If you think about this line, Jack Traven (Reeves) is Sisyphus. No matter what happens when he rolls that rock up the hill and defeats the bad guy, when he wakes up in the morning, it will be back at the bottom, and he will start over. He is dedicated and focused in the face of an unrelenting situation. The world will hit you with problems virtually every day, it seems, but it is your charge to get through it. Besides, think about it this way: theoretically, Sisyphus had a leisurely walk back down the hill to start over, right? Half leisure, half work doesn’t sound so bad.

3 comedy films to break your stress

You don’t always have to learn something or take a lesson away from a movie. Sometimes, you just want to let loose, relax, and laugh your ass off. These three movies will do that for you. And, if you feel so inclined, there are things to take away from these three movies, lessons out of laughter.

Wedding Crashers

If you don’t like this movie, you’re just wrong. This movie is the height of Owen Wilson and Vince Vaughn, and while they did other films together, they just never could quite recapture the magic of two guys crashing weddings to meet girls, only to unintentionally find the loves of their lives while hiding their true selves. So, what can these two knuckleheads teach us?

Love doesn’t exist, that’s what I’m trying to tell you guys. And I’m not picking on love, ’cause I don’t think friendship exists either.

Growth, of course. These two men continue on their terrible paths of behavior until they are caught, and their women make them pay for their indiscretions. This leads to a falling out between the two of them as well. What we pick up from Wilson’s character is that growth and maturing from who you were into who you need to be is the only way to keep lasting friendships and relationships intact. I just justified another watch on that one; you’re welcome.

Superbad

Superbad may be the last great comedy before the world of rip-roaring comedic movies died. Why did they die? Well, because they talk about things that are uncomfortable to talk about, and that isn’t something we handle well nowadays. So, if you want a bit of the old days in a bottle, this is the entertainment you reach for.

He is the sweetest guy. Have you ever looked into his eyes? It was like the first time I heard the Beatles.

I will be honest, I had a hard time pulling a quote from this movie that didn’t have f*** in the middle of it. But this movie, like so many great comedies, is a coming-of-age story that teaches us the harsh lesson that things have to change. As two high school buddies get ready to go off to college, they have to come face to face with each other that they no longer have a crutch. A great lesson in growing up as a man.

Anchorman

Confession time. I hate Will Ferrell. I have always felt that he is drastically overrated. Maybe the reason I love this particular movie is that this is his first true leading role. Every movie following this one seemed to follow the same premise. He is the best at something, then someone comes and takes it away, and now he has to get it back. Blades of Glory, Talladega Nights, Semi-Pro, The Campaign. They all follow this model. Now, having said that, this movie also sticks out as a must because it may be every cast member’s best movie…a rare thing.

60% of the time, it works every time.

What is the lesson of Anchorman? Other than San Diego means Saint Diego? Competition does nothing but make you better. Relish the competition; never be threatened by someone who will make you step up and improve. They are the gift your talent gives you. Ron Burgundy (Ferrell) got better when he embraced the challenge. Embrace all the challenges in life.

15 movies. 15 lessons about being a man. Pop the popcorn, get the soda, and fire up the DVD player (because all of these movies are on DVD) for a marathon in masculine growth and entertainment.