It was a simpler time back then. We grew up watching Adam Sandler as he blew up with his antics on a short but memorable stint on Saturday Night Live. His comedy albums (They're All Gonna Laugh At You!; What The Hell Happened To Me?; et al) gave rise to tracks like "The Longest Pee" and "Ode to My Car" were passed around in mp3 formats by tittering teens (me included!). Sandler soon graced the big screens with The Waterboy and Billy Madison, giving a visual form to the "man-child" humour that he was known for. His films follow a formula of a child-like protagonist trying to operate in an adult world on his own terms and succeeding, and in some way, is exemplary of Sandler's own career with Punch-Drunk Love being his first showcase in a drama playing—you guess it—a man-child.

That said, the wheel eventually turns and we return to what Sandler began, with a sequel to one of his cult comedy classics: Happy Gilmore.

Reprising his role as Happy, the short-tempered hockey player-turned-golfer, in Happy Gilmore 2, we’ll see him navigate the trials of golf stardom, legacy building, and perhaps even a few existential musings—well, as much as Happy can muster.

The teaser trailer dropped just before Christmas, giving fans a first glimpse of what’s to come. Joining Sandler is an ensemble cast as eclectic as it is unexpected. NFL star Travis Kelce makes his acting debut, bringing a touch of sports authenticity and his signature charisma. Music sensation Bad Bunny steps off the stage and onto the green, adding intrigue to a character yet to be fully revealed. Meanwhile, Margaret Qualley brings her dramatic prowess to the mix, balancing the chaos with some heartfelt moments.

Returning fan favourites Christopher McDonald as the ever-scheming and shit-eater-for-breakfast, Shooter McGavin and Julie Bowen as Virginia Venit promise a healthy dose of nostalgia. We won't see Carl Weathers, Bob Barker or Richard Kiel (the actors died 2024, 2023 and 2014, respectively) but, at least, we get to see Rob Schneider in something.

While the release date hasn’t been pinned down, Netflix plans to unveil Happy Gilmore 2 in 2025, giving us plenty of time to rewatch the original and speculate whether 29 years later, a sequel is still able to retain its magic.

About three years ago, Will Ferrell’s longtime friend Harper Steele—a writer-producer who worked with the comedian on Saturday Night Live, Eurovision Song Contest, and more—came out as a transgender woman. And Ferrell responded exactly like a big-hearted, beer-crushing Will Ferrell character: Let’s take a cross-country road trip to talk about it and make a documentary of the whole thing!

The duo worked with filmmaker Josh Greenbaum (Becoming Bond, The Short Game) to capture the entire journey, which would also function as Steele’s first time truly living in the world as herself. The trek includes but certainly isn’t limited to: uncomfortable, teary-eyed conversations in a car, a steak dinner gone wrong and one blissful karaoke night. The result is the hilarious, beautiful, and deeply important Will & Harper, which debuts on Netflix.

Now, it would’ve been enough to show Steele and Ferrell’s sprawling, My Dinner with Andre–style talks on the ride. But that’s not what makes Will & Harper one of the year’s best—if not the best—documentaries. Greenbaum delivered a striking portrait of coming out as transgender in a year that, as of June, saw US legislators consider 617 anti-transgender bills (and a potential president in Donald Trump—who, if he wins, poses a major threat to transgender Americans). We watch as Steele finds support at a rural bar but face staggering hate at a seemingly benign Texas steakhouse. “If you start to engage and listen to people like Harper and so many others, you’ll realise, These are just people who are trying to live their lives,” Greenbaum says.

Below, he opens up about following Ferrell and Steele across the United States, the potential political impact of the film and his next directorial projects, one of which just so happens to be Spaceballs 2. This conversation has been edited and condensed for clarity.

ESQUIRE: Has anyone asked how the road trip was for you? I mean, you also traveled the country.

JOSH GREENBAUM: You’re right! No one actually has asked me that. It was a mix of things. Of course, I’m just so focused on figuring out how to capture the footage.... On the flip side, I was going on this journey with them. Both of them were friends of mine prior to making the film, so they’re certainly the subjects of my film—but there was another added layer of going through all the emotional ups and downs that they were going through. In any given scene, I was in the background—usually in my car—and I could be laughing. Then at some of the heavier moments when they both broke down, I was crying.

You were feeling the emotional and physical toll of a road trip.

I knew there would be some highs and lows but where they came completely surprised me. I’m just thinking of when we have a silly dinner where Will’s going to try to eat a 72-ounce steak [and it was a low]. Then there were times when we went into a bar that I thought was for sure going to be a low. I thought, Oh, I scouted this bar that Harper said she wanted to go in by herself—and I am certain this is not going to go well. Every time I had a preconceived notion—which is certainly a lesson for me and for anyone involved—it [might not always play] out the way you might expect.

There’s a statistic: 70 per cent of people don’t directly know a trans person.... The unknown with Harper became known as soon as she walked into places. She’s so personable and funny that all of a sudden that scary unknown became Oh, okay, she’s cool. She’s funny. She likes shitty beer. And you go, This thing that I was either apprehensive about or afraid of, it’s not so scary all of a sudden. Obviously, it’s a huge burden to put on one person.

Was there a point when you realised that Will and Harper’s conversations could act as a point of entry—and empathy—for people who don’t know much about transgender issues?

That was the intention from the start.... By seeing someone like Will with his friend Harper—and the two of them not so perfectly make their way through these understandably difficult conversations—it does create an easier on-ramp and lowers the bar of entry for people to feel like they can engage. One of the lessons I took was: A lot of us want to engage, be allies, and be there for a friend. But there’s a fear of saying the wrong thing, not knowing what to say, doing the wrong thing, or asking the wrong question. What Will and Harper showed throughout this journey is that a lot of being an ally and a friend is just being there. Listening. You don’t always have to say the perfect thing, provide the best advice, or ask the best question. Just show up.

I feel like a lot of people who watch this documentary will meet Will Ferrell—who is far more even-keeled than his onscreen persona—for the first time.

One of my favourite moments was when I screened Will & Harper for some close friends and family. I screened it for Will’s dad and he was in tears at the end. He hugged me and said, “That’s my boy up onscreen. That’s the man that I raised and know and love.” He said it’s the thing he’s most proud of that Will’s ever done.... Will is an amazing guy and I’m really excited for the world to see the side that I’ve known for seven or eight years now.

Having known Harper for several years, what did you notice in her over the course of the journey?

She has never wanted to be on camera. I dug through archival photos and footage of Saturday Night Live, where she started the same exact day as Will Ferrell. She was there for 13 years. I couldn’t find anything. She’s like, “I would hide. I would dive out of the way.”... Harper grows more and more comfortable throughout the film. By the end, there’s a giant sense of relief and joy. That was just an important part I wanted to convey, which was for so many trans people and queer people, when they come out, the actual feeling is joy. You see that throughout Harper’s journey as she just leans more and more into her joy.

It’s beautiful. You really can see the weight shedding off her back.

Now you should see her. She’s coming out to standing ovations at festivals. I was like, “Harper, keep an eye out. I want your head to get too big!”

I know people keep asking about the steak scene, where Ferrell and Steele are received poorly by the patrons of a Texas steakhouse. But what’s the opposite of that?

There was something about the karaoke scene [that was special]. Harper meets another trans person who has gone through it before. You can see that she’s learning, asking questions, finding a friend and they just bonded.... Will sang—in of course, classic Will Ferrell fashion—“She’s a Lady,” which is very fun and funny. And finally, the three of them settled on a song to sing together, Sonny and Cher’s “I Got You Babe,” which is just euphoric and beautiful.

Will & Harper premieres during an election season. Did you ever see the film as having any sort of political role?

I hope it makes a cultural impact. Everyone on the team consciously did not make what I would call a political film. It’s an incredibly personal film. But that’s where our politics should lie—in the personal. We can talk about all these hypotheticals and you can hear politicians spewing lies about this and that, about kids going to school and then two days later coming home a different gender. Utter bullshit. But the way to combat that is through storytelling—personal stories, levity, comedy and joy. Some people just don’t know a lot yet. What they’re doing is they’re listening to the wrong people. They’re listening to politicians.

We went through this, by the way, with gay marriages. A lot of the same arguments were being made. There was a lot of Oh, what if we let gay people get married? What will they do next?!?... There’s this subtle line that Harper says that I always go back to. It’s when she’s outside her house toward the end of the film, where she’s explaining that she’s just feeling such relief that she doesn’t have to lie and hide anymore. She says that she just wants to be in the world. That’s all she wants to do. She just wants to live.

On a lighter note—and this is a true story—I watched Spaceballs as a kid, but I didn’t see Star Wars until I was in college.

You’re like, “This is a lot like Spaceballs! George Lucas copied Mel Brooks.”

That’s exactly it. I can’t let you go without asking about Spaceballs 2.

Well, there’s not much I can share, other than I’m excited to make it. It’s a still a little ways out. Like you, I was obsessed with the movie. I’m older than you so I had VHS. Back in the day, we didn’t have Netflix. You just went to your seven VHS tapes that you had in your house—and that was one that was on repeat. So I started speaking with Josh Gad and then, of course, Mel Brooks to work on this. I’ve been working with him. He’s 98 and he’s still the funniest and sharpest person. It’s a total joy. I’m still in the doc world. I’ve got another documentary coming out that I can’t really speak to yet, but it’s the distant cousin of Too Funny to Fail, which was a doc about The Dana Carvey Show. That’s coming out earlier next year, before Spaceballs.

There have obviously been so many Stars Wars films and shows since Spaceballs. What’s new to satirise in the current state of Star Wars?

I think you could answer that, right? It’s fairly easy. There’s been a ton of Star Wars content. It’s just exploded beyond the fact that there have been not three but six Star Wars films made—and that’s just in the Star Wars universe. So there’s a lot of new [material to satirise], but we also certainly focus on continuing the old so it is a true sequel.

What hasn’t anyone asked you about Will & Harper yet?

I’m really proud of the music in the film. What’s a road trip without great music? This is the first film I’ve ever worked on that every song was cleared [by their respective artists to appear in the film]. I was told by so many people, “Don’t even try for Bon Iver’s ‘Holocene,’ because [Justin Vernon] never gives it.” I sent a note to Justin Vernon and he watched the scene—and loved the movie—and he granted us permission. Of course, it all comes to an end with the wonderful Kristen Wiig. She wrote a beautiful song to end the whole film.

Is the Academy Award for Best Original Song limited to narrative films?

No, it is not. We’re doing it. Let’s get Kristen Wiig an Oscar.

Originally published on Esquire US

About three years ago, the sketch group Please Don't Destroy—which consists of Martin Herlihy, Ben Marshall, and John Higgins—was backstage at a claustrophobic New York City comedy venue, ready to perform. Covid-19 precautions just lifted, and people were finally going outside to see comedy again. At some point, the trio learns some thrilling, if anxiety-rattling info: Lorne Michaels is in the crowd. Back then, the guys were just NYU comedy graduates and popular TikTok creators. Not only was Lorne Michaels in the audience, but he was about to see them open with a batshit idea they’d never even tried before.

“We had these three 70-year-old men walking out who kind of looked like us, and they were our future selves,” Ben Marshall tells me over Zoom, sitting in the same little room where they write and film their sketches. John Higgins adds, "The guy who played future Ben was maybe 91 years old." After the show, the Saturday Night Live! producer came backstage. “He was wearing an N-95 mask, and he spoke so quietly that I could barely hear him,” Marshall recalls. “You would just laugh after whatever he said because you weren’t sure if it was a joke. Then he said, ‘I’m sure we’ll be seeing you guys soon.’” Michaels then turned around and walked out of the room. “It was scary.”

Of course, "seeing you guys soon" meant "you're hired." Now, Please Don't Destroy is entering its third season working under Michaels, populating Saturday Night Live! with increasingly surreal sketches. But yeah—that night was pretty weird. “If you ask him about it, I’m sure that he wasn’t trying to be weird,” Higgins says. “He was just trying to be nice, like, ‘See you guys soon!’ But for us, it was such a big deal that we were like, ‘What do you mean?!’” The comedians are also releasing their debut film, Please Don’t Destroy: The Treasure of Foggy Mountain, exclusively on Peacock. With the SAG-AFTRA strike finally over, they’re thrilled to talk about it. “I feel like the article should just be called, ‘Download Peacock,’” Higgins jokes.

Below, Higgins, Marshall, and Herlihy open up about about making of Foggy Mountain, casting Conan O’Brien as Marshall's dad, and their earliest comedy shows (one of which may or may not have involved a cow costume).

ESQUIRE: Has reaching a certain level of fame set in yet, or do you still leave the stage after talking to Seth Meyers and go, "Boys, this is insane?"

JOHN HIGGINS: It never gets more normal. We were just on Seth Meyers and we’re told, "Oh, Jimmy [Fallon] has an idea for you guys to rush the monologue. So, while we’re doing Seth Myers, in the back of my head I’m like, "We have to go back downstairs to go do Jimmy?!"

MARTIN HERLIHY: What kinda helps is that we’re working all the time. So, there’s very little time to feel insane.

Have you gained any wisdom since you were college freshmen?

HIGGINS: It would be really sad if we hadn’t.

BEN MARSHALL: When you start doing comedy, you have all these weird rules in your head where you decide you can or can’t do certain things because they’re not cool or smart, or funny. But as you become more comfortable with yourself over time, those things just fade away. Like, our first show was just 10-15 minutes of medieval music playing with John on stage in a cow costume and Martin milking him.

HERLIHY: We look back on some of the earlier shows and just think, What the hell were we thinking? We were like, That’s genius. Just make sure right off the top that they get a bad taste in their mouth.

I’ve heard a lot about this show: Please Don’t Destroy My Farm. It’s your origin story as a comedy trio. Martin plays a farmer, Ben is an angry businessman and John is a cow who doesn’t talk. I heard that John once asked you both if he could talk next time.

HIGGINS: Finally, somebody’s asking! I wouldn’t think that it was going to be awkward, but when they were like, ‘I don’t know, man,’ then it got awkward. I was like, "Fuck, what?"

HERLIHY: I barely knew John at the time, and I really liked the bit of John not talking. It was working, but it was so insane. I was like, "I feel like the best thing we got going for us is that John doesn’t talk."

MARSHALL: We all have very different memories of this event. I thought we were at John’s parents’ apartment, and we were also talking about whether or not we wanted to keep doing shows with the title of "Please Don’t Destroy My X," or just do sketches. So, we were talking around it, in my memory, like, "Well, it’s nice that it’s eventised in that way." I will say, we talk about those first shows all the time as if they’re the worst shit in the world, but I do think—for our first shows ever—they’re pretty funny.

How did it come to be that many of your SNL digital shorts see the host coming to your writing room to do a sketch with you?

MARSHALL: When we were brought on as writers, we were told that we might be doing videos, but after a bit, we thought that we just had to do it. Once they see that it works, maybe they would start letting us do it. Let’s just not tell anybody, get a couple of cameras, and just do a short thing. So, we made that "Hard Seltzer" video as our first.

HERLIHY: It was also production constraints. It was easy to just shoot in our office and we knew when people weren’t going to be here. But we had done so many apartment Tik-Toks that we weren’t going in blind. We knew what to do.

MARSHALL: It’s like a little sitcom we do. Every sitcom has a living room, and ours is the office. Sometimes it’ll even start here and then we’ll go somewhere crazy.

HIGGINS: Rami [Malek] was the first host to do it with us. We just pitch them an idea and if they say yes, we’re like "Great." But in the beginning, we didn’t know if anyone would do it. Rami doing it really set it all off.

Who surprised you the most out of the hosts you’ve worked with so far?

HIGGINS: It happens a lot with dramatic actors. So, whenever they’re even slightly funny it’s like, What the hell? Rami was super funny.

MARSHALL: Brendan Gleeson. Hilarious, amazing guy. Loved him so much. Bad Bunny was so funny.

"Our first show was just 10-15 minutes of John on stage in a cow costume and Martin milking him."

You guys make a lot of jokes about each other’s appearances. Are there ever any when you’ve thought, Guys, that one hurt a little bit?

MARSHALL: I remember one time when we were about to start pitching a joke where someone would be making fun of me, and then like 10 people chimed in all at once and I was like "OK, whoa! Maybe I’ll just write it myself."

HERLIHY: Usually, it’s not our mode of writing. When we know that we need something like that and someone else comes up with it instead of us, we’re like, Oh, thank God.

What was the hardest part about making your first film?

MARSHALL: Editing was probably the hardest. We’re so used to having total say in all our edits and being extremely involved. It was hard to relinquish a little control. We were working here in New York, and it was being edited in Los Angeles. We were still involved. It was just logistically pretty crazy. Also, improv was very difficult to edit. So much of the process is just endless piles of unusable improv. Just hours and days.

HERLIHY: So much of the funniest shit was like a minute and a half of improvising that wasn’t usable. Even if there was one killer thing, we would still have to cut it. We were just so obsessed with making every scene as funny as possible.

Did any bits of improv make it into the film?

MARSHALL: X Mayo is one of the funniest improvers I’ve ever seen in my life. So many of her jokes were pitched on set or just done in the moment. The songs in the tent—where John and Meg are earnestly singing at each other—were both improvised.

When the Internet became obsessed with the nepo baby stuff, did you guys ever think, Look, no one even brings this up unless we’re on Jimmy Fallon? [Editor's note: Higgins's father is Steve Higgins, The Tonight Show's announcer, and Herlihy is the son of former SNL writer Tim Herlihy.]

HIGGINS: Yeah. it was weird but we understood it.

HERLIHY: We’re also three white guys who went to NYU, so we’re not out here pretending like we had the hardest time getting our foot in the door. But I think the work speaks for itself.

Was getting Conan O’Brien to play Ben’s father an inside joke just to get Ben a famous SNL dad as well?

HIGGINS: What’s really funny is that I didn’t think about that at all. It wasn’t until I was watching the movie that I thought, Oh yeah, in this one Ben has a dad who is famous.

MARSHALL: Yeah, it’s funny that it wasn’t a larger conversation.

HIGGINS: We were just like, "Who should play Ben’s red-haired father? Conan O’Brien."

MARSHALL: We also think it’s really funny when guys are obsessed with their dad. Just always vying for their approval. That’s where that came from. Not us, though. We all have great relationships with our dads. [Laughs.]

I feel like a lot of people don’t know that this is Conan’s first substantial role, playing a character in a film that isn’t himself.

MARSHALL: His character’s name is Farley, for some reason.

HIGGINS: I don’t think anyone in the movie even says it.

HERLIHY: I was just calling him “Sir,” which worked for both the character and how intimidated I was.

What would it take to become the fourth member of Please Don’t Destroy? Is there some sort of blood oath, or do I need to find a secret treasure?

HIGGINS: Just show up with two and a half million dollars and you’re good.