The Big Picture

Collider’s Steve Weintraub speaks with actor, producer, writer, and director Ben Stiller about projects past, present, and future.
In particular, the two discuss Stiller’s miniseries,
Escape at Dannemora
, now streaming on Netflix.
In addition to the show, Stiller discusses winning his first DGA Award, working on
Severance
Season 2, reuniting with Adam Sandler for
Happy Gilmore 2
, the documentary for his parents he’s wrapping up, and much more.

In 2018, writer, producer, actor, and director Ben Stiller won the DGA Award for Outstanding Directorial Achievement for his limited drama Escape at Dannemora. The seven-episode series features a stacked cast, starring Patricia Arquette, Paul Dano, and Benicio Del Toro, and is based on the true story of a female prison guard who became romantically involved with two inmates.

In the show, Arquette portrays Joyce “Tilly” Mitchell, the woman who would aid in the escape of two violent men, Richard Matt (Del Toro) and David Sweat (Dano). For the miniseries, which has since found a new life on Netflix after its initial Showtime release, Stiller says, “We had real people playing themselves, we had access to the actual prison, we were able to shoot in the actual locations.” In addition to working off the compelling scripts from Brett Johnson and Michael Tolkin, Stiller’s dedication to authenticity earned him his first DGA Award.

Now, Stiller is hard at work on Season 2 of the hit Apple TV+ series Severance, with a handful of other directorial projects in the works. In this interview with Collider’s Steve Weintraub, the multi-hyphenate, best known for his comedic turns in countless films, revisits past roles like the “incredibly dicey” Tropic Thunder and shares his enthusiasm for reprising Hal L in Adam Sandler’s upcoming sequel Happy Gilmore 2. He discusses the hard work that went into Escape at Dannemora, the deeply meaningful accolades the series received, and his future plans, like the documentary for his parents, Anne Meara and Jerry Stiller, he’s been working on for “almost four years.”

Ben Stiller Wouldn’t Venture to Do a Movie Like ‘Tropic Thunder’ “In This Environment”
“Edgier comedy is just harder to do.”
Image via DreamWorks Pictures/Paramount Pictures

COLLIDER: I was just looking on Reddit, and the #2 story in Movies is a 10-minute unedited scene of you and Robert Downey Jr. doing Tropic Thunder stuff. It made me think, I don’t know if Tropic Thunder could get made today. Do you think it could?

BEN STILLER: I doubt it. Obviously, in this environment, edgier comedy is just harder to do. Definitely not at the scale we made it at, too, in terms of the economics of the business. I think even at the time we were fortunate to get it made, and I credit that, actually, to Steven Spielberg and DreamWorks. He read it and was like, “Alright, let’s make this thing.” It’s a very inside movie when you think about it. But yeah, the idea of Robert playing that character who’s playing an African American character, I mean, incredibly dicey. Even at the time, of course, it was dicey too. The only reason we attempted it was I felt like the joke was very clear in terms of who that joke was on — actors trying to do anything to win awards. But now, in this environment, I don’t even know if I would have ventured to do it, to tell you the truth. I’m being honest.

It’s a completely different world.

Related Ben Stiller Came Up With the Idea for ‘Tropic Thunder’ on the Set of This Steven Spielberg War Movie The idea for ‘Tropic Thunder’ emerged while Stiller was working with method actors on this Spielberg project.

You were eight years old, I believe, the last time the Knicks won the championship. Is this their year?

STILLER: Tough question. I don’t know. I am hopeful that they’re gonna make a really great run. I think the jury is out in terms of the chemistry coming together in time. I have no doubt that the chemistry is going to come together. It’s just that they’re missing a lot of pieces right now. So, I think it’s a better question to ask at the All-Star Break. But I couldn’t be more behind this team. I believe that this team has the chance to go there, and it’s just a question of whether luck will allow for all the pieces to be there and then for them to have the time to get that chemistry rolling, which is starting to happen.

You are a very vocal and hardcore fan. How much would you pay to have the Knicks win in the next five years?

STILLER: [Laughs] Well, the thing about a championship for your team is you can’t pay for it because you can’t buy that. Like what would I give up?

Pretty much.

STILLER: I’m willing to sacrifice a lot. The thing is, I’ve always loved the Knicks. Actually, I did one of those Proust Questionnaires for Vanity Fair, and they said, “What is your idea of despair,” or something, and I was like, “The 2014/2015 Knicks.” The thing is, this Knicks team, you just love this team. I am so all in on this team. So, I’m rooting for them. I believe it’s gonna happen. But more than anything, these guys have so much heart and they’re so human, and they’re so connected to their fan base that no matter what, I’m with the team.

“There’s a Good Reveal” for Ben Stiller’s ‘Happy Gilmore 2’ Character
“He has no redeeming characteristics.”
Image via Universal Pictures

I couldn’t believe when Adam Sandler decided to do Happy Gilmore 2 . I love the first one so much. For me, he’s playing with the third rail because this is such a beloved movie. What was it like getting the call to come back as Hal L?

STILLER: I’m always ready to play Hal L. You don’t get the opportunity to play Hal L that often. Weirdly, I got to do Hal L in Hubie Halloween a few years ago. He had him at the beginning of that movie working at this insane asylum. So, Hal L — I’m saying this now in retrospect because I just did it — was so much fun. As we were doing and I was there with Adam, I was flashing back to whatever it was, however many years ago, and just being so grateful that we’re both still here and able to connect. I love Adam. He’s a dear friend. And the opportunity to do that guy is just so much fun because he has no redeeming characteristics. I think he’s a good person inside. I think he’s misunderstood. It bothers him that everybody loves Happy. You don’t have to worry about making him likable, so it’s really fun to just go for it. We had the best time.

Your photo of Hal is the photo on IMDb for Happy Gilmore 2 . The photo of you on set literally went everywhere. It just exploded on the internet. I am curious how much your phone blew up once that photo got out there because everyone was talking about it.

STILLER: Yeah, everybody. All of a sudden, I was like, “Oh, I guess somebody took a picture,” because I saw it everywhere. It was great. I was like, “Oh, this will be fun when it comes out,” but it’s nice to know that people actually care about Hal L — even that they remember his last initial, L. There is a good reveal in the movie having to do with Hal’s name that I won’t say. There’s a good surprise there.

Related ‘Happy Gilmore 2’ Adds Yet Another Musician to Its Cast The film stars Adam Sandler and Bad Bunny.

I really enjoy when you’re behind the camera directing. Which of your projects changed the most in the editing room in ways you didn’t expect going in?

STILLER: Oh, wow. Well, I have to say, honestly, every project evolves in the editing room because it becomes the last draft of the movie. I’d say even on Severance, we do a lot of work in the editing room in terms of how to tell the story and sometimes, learning things when we edit that, we go back and rearrange. It’s such a weird reality, we’re always learning about it as we make it. So, there’s a lot of reordering and things that happen on that show But it’s always a process, and I think you have an idea of how something is gonna play, but until you actually see it, I always find there’s so much you can take away, so much you could allow the audience to fill in when you actually see something, especially with good actors.

Ben Stiller Is Working on a Documentary for His Parents
Image via CBS

Obviously, you’re working on Severance Season 2 right now, but do you know what you’re gonna direct after?

STILLER: Good question. I don’t. I’ve got a couple of things that I’ve been wanting to do. One of them that I’ve been sort of nurturing and nursing along for a while is Slaying the Badger, which is about the 1986 Tour de France and Greg LeMond, the first American to win the Tour de France. That’s a story I really wanna tell, and that could be the next thing. But honestly, it’s been full-on working on Severance.

Then the other thing that I’ve been working on is this documentary about my parents. This is something I’ve been working on for the last almost four years, and I think we’re getting to the point now where I think I’m gonna finish it up in the first part of next year. That’s been taking up my time.

I can’t wait to see this. I loved your parents, and your dad made me laugh countless times.

STILLER: A lot of people know my dad from Seinfeld and King of Queens, and some people know my mom, and then some people of a certain generation know my parents together as a comedy team. It’s so much about their relationship and how they worked together and how they evolved as creative people while also having a marriage, and then also my own life and growing up in that, and how that’s sort of affected my own relationships. It’s really been an interesting process. I guess for me, now having lost both my parents, so many people don’t have all of this incredible archival footage of their parents that exist, so I feel very lucky to have that, but also, it’s kind of daunting to dig into all of it and get in there. It’s fascinating, too. It’s been a really interesting process.

Do you think it’s like a two-hour movie? Because it could be a lot longer. There’s so much footage.

STILLER: I think it’s gonna be a movie. I like movies, too. [Laughs] It’s been great doing television because I think you’re allowed the tools and the facility to work on a certain scale in television that’s harder to do in certain genres in movies these days, but I love making movies and so I feel like this one’s a movie.

Do you envision a Toronto or a film festival-type environment to premiere?

STILLER: Yeah, I think so. At the end of the day it’s really a movie about families, parents, children, marriage, work/life balance.

‘Severance’ Season 2 Is Going to Explore the “World for the Innies and Outies”
Image via Apple TV+

There are a lot of fans of Severance who cannot wait for the show to come back. What do you want to tease them about Season 2?

STILLER: Knowing how Season 1 ended, there were so many obviously big questions. We now have sort of opened up the world for the innies who have been on the outside world, so we felt like there was a responsibility to open up the story in that way and ratchet up the stakes and really dig into these relationships in terms of what Mark is dealing with in this very unique situation of the innie and the outie. The first season was so much about Mark trying to navigate this world, and then now realizing, having had his innie be on the outside world and learn this incredibly impactful thing about his wife, to follow up on that and that journey, to me it’s always been about Mark’s journey towards figuring out who he is.

Now that the show has won awards and Apple and everyone knows how good it is, when you guys were making Season 2, how much were you thinking about, “Oh, we might do Season 3 or even Season 4. We need to know where we’re going and make sure that we have a path that will work if we get to do more seasons?”

STILLER: Yeah, I think it’s very important. You have a responsibility to the audience that you’re going somewhere with it. That’s always been a part of it for us, really understanding where it’s heading to, and Apple’s been really supportive of that and been sensitive to what the story is and not saying, “Okay, this is something that has to keep going as long as it’s successful.” It should go as long as the story goes, and that’s something we have an idea of and we’re working towards as we’re starting up our Season 3 work.

Netflix Changed the Trajectory of ‘Escape at Dannemora’

Let’s get into why I’m talking to you today. What is it like for something that you made six years ago to suddenly get a new life on Netflix where I’ll bet you more people watched it on Netflix in the first week than originally saw it?

STILLER: That’s the amazing thing about Netflix. It’s changed the business, and in this incredible way where I think one of the things that we’re seeing is that these shows that didn’t necessarily get a lot of viewership or attention for whatever reason are now all of a sudden given a platform. It’s incredible, honestly, because that never existed before in our world, to have the opportunity. Maybe a movie would get a re-release on an anniversary or would be on cable or something like that, but for it to be discovered like this?

The situation on that show was it was made on Showtime, and in the last few years, with Showtime and Paramount+, all the things have been changing in the streaming world and have made it difficult for people to really find it. So, to have it up there, and then to see in the first week, it was getting in the Top 10, it was, for me, so gratifying. I’m so proud of the work that everybody did on it, and it was such a really great experience to dig into that world and to work with Michael Tokin and Brett Johnson, the writers, and how we were able to get access to these people’s stories and to try to really tell the story in a very truthful way and also make it, hopefully, dramatic and intriguing too.

It’s called a seven-episode series, but part seven is two parts, so isn’t it like an eight-part series? I don’t understand why it’s listed as seven episodes.

STILLER: It’s interesting, it was originally eight parts, but then when we did it on Showtime we did Episodes 7 and 8 together as one piece. Then on Netflix, we did a version where we broke it up that they wanted to have, but I always preferred it as seven and have the last one be a full episode. But I saw on Netflix that they broke it up into two episodes. I watched it, I see where it stops, and it kind of just keeps going, and it has actually an interesting stopping point. But for me, Episode 7 was always just that two-parter together. It should have been together, but I have no complaints. It’s on Netflix.

Ben Stiller Says ‘Severance’ Season 2 Is the “Toughest” Thing He’s Directed
Image via Apple TV+

A lot of people don’t realize you directed all parts. I’ve spoken with 1,000 directors, and they all talk about it being a marathon. Was this the hardest thing you’ve directed just because of the sheer volume of shooting days?

STILLER: It was, up until Season 2 of Severance, which was 186 days, and I directed half of the episodes, but as a producer, was there every day. It was challenging because of the strike and all that stuff and just what we were doing. So, up until then, the Dannemora shoot was the toughest, but it was also a really positive experience, that shoot. Working with those actors and the crew, everybody was so engaged, and having our technical advisors who are from Plattsburgh and Dannemora were part of it, some who had been prisoners at the prison, some who had worked as corrections officers, or in the state police. We had real people playing themselves, we had access to the actual prison, we were able to shoot in the actual locations. The scenes at the end, where Matt meets his end, and the trailer that he spends the last night in, are the actual trailer, the actual spot. It was pretty incredible to have all that.

For me, it was the first time I had been really directing and not acting in a very long time, probably since Cable Guy, and I really enjoyed that part of it, to be able to just focus on that and to work with Jessica Lee Gagné, our cinematographer who went on to shoot Severance with me, and Geoffrey Richman, the editor who edited, and Malcolm Jamieson, the other editor, two great editors, but Jeff also edits Severance. So, it’s like that team stayed together for Severance.

Related The 9 Things You Need To Know About ‘Severance’ Season 2 “Hey, kids! What’s for dinner?”

All the performances on the series are fantastic, but Patricia [Arquette] is operating on another level. When did you realize she’s shooting three-pointers on every take?

STILLER: Early on. I love Patricia. We’d worked together on Flirting with Disaster back in the ‘90s as actors. David O Russell directed it, and I’d never directed her, and we hadn’t really stayed in touch. On and off a little bit. We had the same manager who’s a good friend of ours. But then when we got together on Dannemora and we started talking, I just felt so comfortable with her. She’s such a good person, and she’s so without ego. The willingness to transform her body to just find the core of that character who is doing things that could be interpreted as not good, but she found the goodness in that character and the humanness in that character. She’s just brilliant. She’s subtle, and she’s real, and she’s fearless.

When her and Paul Dano had to do those sex scenes in the back room, which were incredibly challenging for actors to have to do something like that, and the way that they brought such professionalism to it and willingness to be so real, when I saw them do that work, I was like, “I’m working with people who are just true artists.” And Benicio [Del Toro], every scene, I’d never worked with him before. His approach to really finding the moment and what was gonna be interesting in every scene for this character, and again, to give him humanity, too, and a mystery and all of it, for me as a director, I was learning so much. Honestly, I was learning so much as an actor watching these actors. I’m there directing and watching, but I’m learning more about the approach to the work that I really took with me, too.

Image via Showtime

Putting Benicio in anything is like putting a cheat code in a video game.

STILLER: For sure. Because he makes it his business to figure out how he’s going to inhabit this character and give you something that’s fascinating.

What do you think might surprise fans to learn about the making of the series?

STILLER: Well, we shot it backwards. We were starting in the summer and going into the winter, so we had to start with all the escape stuff first. We shot at the actual prison, at Dannemora Clinton Correctional. We shot there for, I think, three days. We shot outside for a couple of days, and then we shot inside on that yard. That yard is just an incredible place that’s been there for almost 70 or 80 years. It’s almost like a Roman amphitheater or something. Like I said, there were real people playing themselves. Chuck Guess, who was the New York state trooper, was the one who led up the manhunt, was playing himself. We had, as I said, the real locations. We had a lot of fun doing it, weirdly. It was just a great experience.

You have acted in and directed so many things. What shot or sequence of your acting-directing career was the hardest to pull off and why, and what was the hardest shot or sequence in Escape ?

STILLER: Career-wise, I immediately go to the last act of Tropic Thunder — all the action stuff at the end of Tropic Thunder — because we had that whole sequence where the guys escape, and that was the point in the shoot where there’s meta moment of real life that started to fold in on the movie where we were starting to go over budget, and the studio was calling up and saying, “You gotta figure this out.” Obviously, the movie was sort of about the same thing. I remember there was this truck that had to go down the road, and then the truck gets shot and blows up, and then we had to run across the bridge and then the helicopter, and we were doing it in sequence. I remember thinking, “I have three weeks to get down that road. We gotta figure out how to do it.” Somehow, we figured it out, but I remember that being super challenging.

Image via Paramount Pictures

Then, on Dannemora, probably, it was the two days that we were shooting in the prison there in the real yard there. The deal with the prison was that we could use the yard, but we couldn’t use any of the inmates who were there. I wanted to use all people who had prison experience, people who had been inmates, so we found actors who had been inmates in a prison, we rehearsed in a field that we sort of mapped out to look like the yard inside, creating all their little areas where they would be assigned to, where they’d make fires and things like that. Then we rehearsed it all in a field, like an athletic field, near the prison for a day. Then we had to bring everybody in, we all had to go in and get searched and everything and brought out there, and recreate all that for the whole day and then leave with fake guards and fake prisoners and all that, and then go back in and do it again. That I remember being incredibly challenging logistically, but at the end of the day, it’s also one of the things that I’m really happiest with in the show, too.

For Episode 6, you shot on 16-millimeter. How did you come up with the decision for 16mm, and do you think if you were shooting it now, you would do something different with the technology that’s available, or do you think 16-millimeter just works no matter when you’re shooting something?

STILLER: We did that in Episode 6 just for the Tilly flashback because we wanted to have a different feel for it. To me, I’m all for film. I would shoot everything on film all the time if I could. Dannemora was too expensive to shoot because we were shooting so many cameras and so much footage, but it gave it a feel. It was a flashback, and it gave it, I think, much more of a visceral feel. I’m one of those people, like if it’s something where you’re like, “Hey, it’s supposed to be Super 8 footage,” and the VFX guy says, “Yeah, we can make it look like that,” I’m like, “But why don’t we just shoot it on Super 8?”

This is just me, and probably because I’m old, but everything I do when I shoot on digital is always to try to make it look filmic. And Jessica, when we met, who’s much younger than I am, what I loved about her work — she had done a movie called Sweet Virginia that I thought was really beautiful, and that’s how I saw her work — her sensibility is that’s how she approaches working digitally. So, for me, that’s always how I like to approach it, too.

I wish more people would spend more time with the aesthetic of how something is gonna look because it really diminishes something that could be really great when it just looks like shit.

STILLER: I agree. Film is a visual medium, and there’s so much you can say with an image. You don’t even have to have any dialogue. That’s what I constantly find, even when we’re working on scripts is, “How much can you take away?” Because in film and cinema, shows, movies, that’s what you’re taking in — you’re taking in these images, and they tell you so much. So, I’m the same way.

I don’t know if you know this, but Danny Boyle just shot 28 Years Later using the new iPhone and really big lenses on the iPhone. Have you heard about this?

STILLER: No.

Related Ralph Fiennes Confirms Danny Boyle Shot ’28 Years Later’ on an iPhone [Exclusive] Boyle’s post-apocalyptic follow-up will star Fiennes opposite Aaron Taylor-Johnson and Jodie Comer.

He did, and I’m very curious what it’s gonna look like. The iPhone obviously has an incredible camera, but using a real lens on top of the iPhone, I’m just so curious about what the image is gonna be.

STILLER: Yeah, and also, so much of what your image looks like, no matter what you’re shooting on, is what your lenses are that really forms it. For us on Dannemora and also on Severance , we go for the vintage lens packages that we could get from Panavision, from the ‘80s and sometimes the ‘70s, both shot anamorphic. I always love it when you get a lens from Panavision, and then they’ll give you the history of what movies were shot on that lens. That’s the coolest thing ever to me. It’s like, “Hey, this is a Tootsie lens!”

So Episode 6 you shot at the end so Patricia and Eric [Lange] could lose weight. I believe you allocated a month, and then Eric had a birth, and then you had a little bit more time. How concerned were you, honestly, with Patricia and Eric losing the weight because it’s a lot of weight that they need to take off and not that much time?

STILLER: Look, that stuff is not easy for actors. Eric gained weight to play Lyle in the beginning, so I felt like he understood how to take it off, and Patricia the same thing. They both are so committed as actors that I knew that they were gonna do what they needed to do. I felt lucky that we had the time to do that. It ended up making a really big difference. Sometimes you’re not afforded that in the schedule. Also, at a certain point, there was even discussion when we were over budget about cutting the flashback episodes from the studio, and I was like, “No, that’s kind of the whole point of the show.” So, you take your stand on things like that.

You can’t say enough about Paul Dano, too, in terms of his commitment level and playing a character where he buffed up and started lifting because that is not a typical Paul Dano role and he really inhabited David Sweat. We went to see David Sweat, Benicio, Paul, and I, and sat with him for about five hours, which I remember, after that meeting, I saw how much Paul just soaked that in and came away with a character from that.

Image via Showtime

I love Paul’s work. It all works because of the performances. If you don’t buy into the three of them, you don’t buy into any of this.

STILLER: As a director, you want to just be able to put the camera in a close-up on an actor, and when you have a great actor, they’re gonna fill that frame, and you don’t have to get in the way of that.

Winning the DGA Award Was More Than Just Recognition for Good Work
“You can get in your head about all this stuff.”
Image via Showtime

What was it like winning the DGA Award for Outstanding Directing — Miniseries or TV Film for this project?

STILLER: Probably one of the best things ever for me, as a kid who wanted to be a director since I was eight or nine years old. A lot of that stuff is in the documentary about my folks, like shooting Super 8 as a kid. To have that acceptance by your peers, it’s kind of the cliche, but it’s really just the best feeling because I always wanted to be a director. So, it was a great feeling.

I have to know, so you’re going to the event that night, did you have a good feeling? How much had you prepared a speech? How much are you in your head, or were you just like, “I’m just happy to be here?”

STILLER: I did not think I was gonna win. I secretly hoped I would win, but these awards things are so crazy. I mean, look, Tropic Thunder is all about that. You can get in your head about all this stuff. It was very exciting. Just to be invited to it was so great because I had not been before, and I’ve been doing this for a long time, and then all of these amazing directors are there that you get to talk to and say hi to. It’s funny, Carl Weathers happened to be there that night, and that was the only time I ever got to meet Carl Weathers, so I felt really lucky that I got to talk to him. It was weird. [Laughs]

When you’ve been doing it for so long, and you’re kind of used to all this stuff, and it doesn’t really ever necessarily happen that way, it’s like, “Oh, okay, well, this is great. This is fun. I’ll take it.” It is exciting, and there’s a rush to it, but this kind of stuff, it’s so hard because you see all the people who do such great work and don’t get recognized for it necessarily. So, whenever it happens, it actually comes together, you’re just appreciative, especially after being in the business this long. When it’s coming from other directors, that’s the best feeling.

Related ‘Escape at Dannemora’ Review: Showtime’s Tense, Finely-Crafted Drama Chronicles a Bizarre True Tale The miniseries is a showcase both for its lead actors and Ben Stiller, who directed all 7 episodes.

You know this because you’ve worked on 1,000 things, you can have a great script, great everything, and it just doesn’t come together. There’s something missing. What was it like for this project to have it come out, have such positive reviews, and have so many people saying, “That’s great?”

STILLER: Again, it’s the same thing. You do it for so long, and every time you go out with something, you’re putting out your best work, or you’re trying to put out your best work, your best effort. Depending on what it is, sometimes you go, “Okay, I get it why that didn’t work, or people didn’t see that,” but it just feels kind of like, “Well, this is just what I’ve been doing.” It’s nice to have that approval. It’s nice that everybody is gathering around it and that it is getting that recognition.

But then there’s also the other side of it, too, where it’s like, when you do something that everybody doesn’t love or like, and you’re like, “Well, I don’t know. I don’t think it was that bad.” You always feel like you’re putting out something you feel connected with if you’re doing work that’s honest and coming from you. So, you take the good stuff, and then you let the other stuff kind of roll off of you. But that’s not easy. [Laughs] My whole life, I’ve been trying to navigate all that stuff. At the end of the day, I guess having done it as long as I’ve done it, you have to step back and go, “Okay…” The bottom line is what you said at the beginning of our conversation, I really am getting to do what I love to do, and whenever something doesn’t go well, my sort of lizard brain part of me is always like, “Oh, I just want it to go well enough that I can keep doing what I love doing.” I don’t want the repercussions to be like, “I can’t keep working.” And I know that’s a very sort of out-of-work actor kind of thing, but that is the way a lot of creative people feel because you just wanna be able to keep having the opportunities to do it, and luckily, I’ve been able to have that.

As I’ve said a few times, I really enjoy when you’re behind the camera directing. When did you realize, “Oh, I’m gonna be able to keep directing. They like my work. I’m gonna get the financing to keep doing this. I made it?”

STILLER: Well, I have to say, when the movies that I was making were doing good at the box office, obviously, that kept things going. But really, for me, Dannemora was the first thing that I directed that I felt like, “Oh, people will want me to direct still because they’re appreciating this thing that is not connected to something that I directed that I acted in also.” And I think, for me, that was a feeling of, like, “This is great,” because I love making these kinds of things that aren’t necessarily comedies, and that people are accepting that and I can do more of that. So, honestly, that’s something I felt on Dannemora.

Ben Stiller Wants You to Check Out This 1998 R-Rated Romantic Drama
Image via Prime Video

You’ve directed and acted, again, on countless things. What is something that you really wish more people had seen that you worked on?

STILLER: I’ve always liked that little movie Permanent Midnight that I did back in ‘97, ‘98 about Jerry Stahl, the comedy writer. It’s a true story. He was a heroin addict, and figured it out. I just always felt that was a good little movie. Every once in a while, someone will shout out, “Hey, Permanent Midnight!” It’s great.

I can’t imagine what it’s like for you in an airport because everyone who comes up to you is gonna want to talk to you about something different.

STILLER: Yeah, you never know what it’s gonna be, which is great. Again, as time goes on, I’ve come to appreciate it more, honestly. I’m getting older, fans are getting older who have been with me over the years. It’s a nice feeling of continuity, and I appreciate it.

You can watch Escape at Dannemora on Netflix now.

Escape At Dannemora A female prison employee in upstate New York becomes romantically involved with a pair of inmates and helps them escape.Cast Benicio Del Toro , Paul Dano , Patricia Arquette , David Morse , Eric Lange , Bonnie Hunt , Gregory Dann , Daniel Johnson , Dominic Colon , Jeremy Bobb , Skipp Sudduth , Amber Gray , Micah Stock , Michael Imperioli , Leo James Davis , Charlie Hofheimer , Jim Parrack , Richie Allan , Carolyn Mignini , Charles Prendergast , David Neal Levin Creator(s) Brett Johnson , Michael Tolkin Expand

Watch on Netflix