The Fort

The Monday blog · April 21, 2025

A cure for lonliness

By Dan Trink, co-founder of The Fort · 5 min read

In honor of the trailer being released for Happy Gilmore 2, here are the top 5 Adam Sandler comedies according to yours truly.

5: Billy Madison. This is the foundation upon which all of the Sandman’s early comedies were built as it establishes the formula of “lovable man-child charms his way into a better outcome than he probably deserves”. Plus it has genius dialogue such as “Soooo hot. Want to touch the heinie” which, honestly, makes me wonder how this wasn’t nominated for Best Original Screenplay at the 1996 Academy Awards.

4. 50 First Dates. Ok, perhaps this isn’t the greatest movie in the classic sense. However, this story of a guy who falls in love with a girl who doesn’t remember him every morning when she wakes up appeals to my soft side. Plus it’s got Drew Barrymore in her prime and who can resist that, really?

3. Big Daddy. This movie has tons of problems - like, I don’t know, using a child in order to manipulate your desired relationship with a woman. And the kid - actually played by two kids - is terrible (bonus fact, they are terrible as Ross’s kid on “Friends” as well). But Sandler’s character went to Syracuse and I probably quoted Rob Schneider’s foreign delivery guy claiming that George Washington’s teeth were “made from wool” more times than I am proud to admit.

2. Happy Gilmore. Curveball here as this would be on top of most dudes list but I have it in the penultimate spot here (I’ve been trying to work the word “penultimate” into a blog for 3 years now). Shooter McGavin is the perfect villain (perhaps only second to Apollo Creed in the first Rocky movie who is played by Carl Weathers who is also, coincidentally, in this movie). But as I mentioned what makes “Happy” so beloved by so many is it’s the greatest execution of the “lovable man-child” trope we discussed in Billy Madison. Plus it’s cool to see someone smash a golf ball with a hockey stick.

1. The Wedding Singer. Sure, call me a softy for putting a romantic comedy at the top of this list. But when you have the perfect soup of Sandler, Barrymore, Christine Taylor, 80s nostalgia, a smarmy limo driver, a grandma who pays for music lessons with meatballs, a Boy George impersonator and a cameo by Billy Idol how could you put anything but this movie at the top of the list.

Sandler is seemingly a guy who has it all.

He’s got a great family. He puts his friends in all his movies so he can spend time with them. He dresses exclusively in hoodies and basketball shorts. I’ve never heard anyone say a bad word about him.

But, truth be told, it’s none of the aforementioned performances or even his classic characters such as Canteen Boy, Opera Man or one of the Gap Girls that are my favorite. It’s not him singing the Hanukkah Song or a heartfelt tribute to his friend Chris Farley either.

No, my favorite bit of Sandler happened recently when he accepted the Mark Twain Award for achievement in comedy.

As far as I can tell, the Twain award is a pretty big honor, equivalent to a Kennedy Center Honor but for comics. Past winners have included legends such as Richard Pryor, Lily Tomlin, Bob Newhart and Carol Burnett.

Most of these comics use their acceptance speeches to do what they do best, be funny.

And, sure, Sandler’s speech had its funny moments but the part that really sticks with me is when he was talking about his older brother, Scott.

He starts by saying that Scott was always calm around him, which I found an interesting word choice. But, when you think about it, when you grow up in a house with siblings, having a calming influence can actually be a wonderful thing.

But then he goes on to talk about how Scott was his biggest cheerleader when they were growing up. Telling him how funny he was. How he should become an actor, that he’d be great at it. That he was really great at playing guitar.

In fact, it was Scott that set up Adam’s first stand up gig in a small club in Boston, almost without Adam’s knowledge.

“I had no idea what I was doing,” Sandler says in the speech. “I didn’t prepare. I didn’t know what I was going to say. I was just going to go up there and wing it.”

And though Sandler sort of blacked out during the 5 minute set, he realized that no one laughed and that he bombed.

But as they were driving home from the club, Scott - once again playing the role of supporter - told Adam how great he was. Sure, he may need to do a better job preparing, but he was by far the funniest one and that the crowd loved him.

“Are you sure,” Adam asked him.

“No doubt,” Scott replied. “You were the best one there!”

And I just love this so much.

I love how Sandler tells the story, standing on the stage in a rare time he is wearing a suit with the award in his hand, getting choked up with gratitude.

And I love Scott. Even though I had never heard of him before or have any idea what he looks like or what he does. What a tremendous person you must be to give your kid brother unwavering support like this.

When we are toddlers and little children, we get such enthusiastic support for all our accomplishments. We crawl for the first time or pull ourselves up to our feet using the arm of the couch for support or say “Dada” or write the letter “B”.

Our grandparents cheer. Our Moms look on in pride. Every accomplishment is a celebration that is written down in a baby book or shared on Instagram.

But as we get older. As we get more self-sufficient and gain more independence and the world begins to be us down, this starts to go away. And we are more likely to hear about how we are a disappointment or we didn’t score well enough on our SATs to get into the college we wanted and the negative self-talk starts to take hold.

And how sad and troubling this is. And how happy I am that Adam Sandler had someone in his life to reverse the cycle.

We push people hard in our gyms.

The programs are challenging and, like I’ve mentioned so many times before, training has to be hard to be effective.

But we also fill the room with love and support. We are excited when you walk in the door. We cheer when you hit a PR. We live for the moments when we get to witness you surprising yourself with what you are capable of.

If we do nothing else but provide an environment of support and positivity in what, for very many, can feel like a negative world, I’ll consider us to be a tremendous success.

Truthfully, it might be the best thing we ever do.

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