By 2007 streaming technology was beginning to captivate investors and audiences. While several sites vied for attention, the big player was YouTube. It had launched in 2005 with help from Silicon Valley VC firm Sequoia Capital and—thanks to early viral hits like Saturday Night Live’s digital short “Lazy ­Sunday”—would soon be getting 100 million streams a day.

MARK KVAMME (partner, Sequoia Capital, 1990–2012)

My son was a fledgling comic at the time, and he said to me, “I can’t find anything funny on YouTube. They should have a thing like Hot or Not, where there’s a voting system.” It was a good idea, but it would have to be something separate from YouTube. And it just so happened that about a week later, I had a meeting with Michael Yanover down at CAA.

MICHAEL YANOVER (head of business development, CAA)

YouTube’s growth had been staggering. I said to Mark, “It’s entertaining but in an amateurish kind of way, like America’s Funniest Home Videos. Isn’t there room in the marketplace for more professional video?”

MARK KVAMME

The idea was to get the best and brightest from Silicon Valley together with the best and brightest from Hollywood and see what they could do. But it was a very confrontational time between Hollywood and Silicon Valley, because of the copyright problems with YouTube and other sites.

DICK GLOVER (CEO of Funny or Die, 2008–2015)

This was pre-social-media, and YouTube was doing to the world what Google and Facebook are doing now—just sucking everything into a vortex, taking everything in. There were plenty of cautionary tales about building something outside that ecosystem.

MICHAEL YANOVER

As we were thinking on it, Will Ferrell—who was a client of CAA—was putting together a company called Gary Sanchez, with Adam McKay and Chris Henchy. Their original premise was to make movies, but they were also contemplating making TV shows. We met with them in a trailer on the Blades of Glory set to pitch this idea of a comedy-video site. We told them, “The consumer doesn’t want to see something too slick, too Hollywood. They like to see professional, and with recognizable people in it, but let’s not drive up a big budget. Let’s keep it guerrilla-style.”

ADAM McKAY (cofounder)

We were just like, “Whatever.” We remembered the first dotcom crash from the early 2000s, and we were superdubious.

WILL FERRELL (cofounder)

We’d seen a number of comedy websites that had failed, and we really weren’t convinced that the internet could be a destination for short-form comedy.

MICHAEL YANOVER

It was stalled out until one seminal meeting when Will and Adam were barricaded in a room, writing the script for Step Brothers.

MARK KVAMME

When the writers are writing a movie, they go off and hole themselves up in some crazy place for weeks on end, so they can finish the script. And they were in the middle of writing, so we all piled into their room in this old, junky hotel.

WILL FERRELL

Eventually, the financiers needed an answer, and we ultimately felt like we had nothing to lose. In hindsight, I guess we didn’t give ourselves enough credit for being able to create interesting and lasting material.

ADAM McKAY

I did kind of miss doing sketches the way we used to do at SNL. Our manager Jimmy Miller was the guy who pushed us: “If you treat it as pure fun, this could be really cool for you guys.” And we liked the idea that anyone could put sketches up, that it was just an open door. If there’s a funny sketch, we’ll put it on the front page.

MARK KVAMME

Initially the idea was to bring on other comics too. So we went to see a couple of other guys’ managers, and everyone said, “No, this is stupid. We’re not going to do it.” Or they wanted some exorbitant amount of money.

MICHAEL YANOVER

We knew we were going to start it really quietly—no promotion, no press. Initially we were just going to put a few videos out there, see how everyone reacts, and then let it spread from there.

ADAM McKAY

My daughter Pearl was going through the stage that some kids do go through, where they’ll repeat anything you say. So my wife, Shira, and I had been doing this game: Shira would say something to her in French, and I would give her, like, a Nietzsche quote or a hip hop lyric, and Pearl would repeat it remarkably well. I had a buddy, Drew Antzis, who liked film stuff, so I called him up and said, “Can you come by Will’s guesthouse? I’m going to be there with Shira and Pearl and Will, and we’re going to do this little idea.” He just showed up with his camera, and we shot it in like 40 minutes, no exaggeration.

DREW ANTZIS (writer-director-producer)

There were a few times where we had to really kind of egg her on and say, “No, don’t walk away. Please come back.” I think it was after Will’s son’s birthday party, and I think there was a little bit of sugar involved, so it was pretty energetic.

ADAM McKAY

The first 10 minutes of filming were a train wreck. She was just too distracted by the room. At one point I thought, “Oh, this was a mistake.” And then Will started jumping in and giving her the lines, and once she was able to look at Will—and Will’s obviously great with kids, he has three kids—we started to get on track.

DREW ANTZIS

What you see on the site, with the exception of the title card, was the cut that I brought to them. I showed it to my wife’s friends as a little focus group, and it was getting huge laughs. I felt like, “Wow, this is really cool and funny. I want my name on this.” And then everyone was like, “Nah, let’s not put our names on this yet, just in case it totally backfires.”

WILL FERRELL

I just tried to have an honest conversation with her—as honest as one can have with a belligerent 2-year-old landlord.

ADAM McKAY

My wife said, “Don’t you dare make our daughter a child star.” And I was like, “Honey, it’s a goof-around video. Because of Ferrell, it’ll get like a million hits. Don’t worry about it.”

MICHAEL YANOVER

We said, we should email 10 friends with a link to this website. And that’s it. That’s the marketing plan.

CHRIS HENCHY (cofounder)

I was here in New York when we put “The Landlord” up, and I remember it had about 100 views when I went to lunch—and when I came back, it already had 60,000 views. We were like “Oh my God. This is working.” I was like, “Let’s shut it down, it’s too big!” But it kept going.

ADAM McKAY

Within a week, The Ellen DeGeneres Show wanted Pearl on the show, and People magazine wanted to do a spread. Jackie Chan was doing some movie, and they needed a little kid, and they wanted Pearl to do it. My wife was so pissed at me: “What have you done?” [Laughs.] We said no to all of it.

LAUREN PALMIGIANO (writer-director-producer)

It was the perfect storm of cursing baby and celebrity and the internet. One million views … 2 million … 3 million. We were calling each other saying, “What’s going on?” I remember McKay yelling, “We’re going to be rich!”

KRISTEN BELL (The Good Place, early Funny or Die star)

“The Landlord” was dropped in my email box by 10 different friends who all knew I’d enjoy it. There was something so inspiring about it. In this business, you have to have so many ducks in a row to actually create something. It’s such a unique idea to say, “Fuck all that. Let’s just grab a camera and do it. Let’s give opportunity to people who have ideas, not necessarily people with extensive résumés and overseas value.”

JON HAMM (Mad Men, early Funny or Die star)

There was so much weird shit out there, and you felt like you had to know somebody or have a cool in somewhere to know what videos were worth your time. The idea that something would survive on its own merit was kind of interesting.

CHRIS HENCHY

Our agents and everybody else started coming at us: “What do you have next?” And we’re like, “Is Will going to have to do a 70-million-view hit video every month to keep it alive?”

MARK KVAMME

For the launch, my son Michael put up a video that got something like 300,000 views—him doing stand-up as a teenager, telling a dolphin joke. By Monday or Tuesday the following week, when the media picked it up, we were serving about 20,000 video plays a second. It’s a miracle the site didn’t crash, except for a few hours later in the week. We soon went from one server to 100 servers.

JAKE SZYMANSKI (writer-director-producer)

Before Funny or Die, I had been trying to upload my comedy shorts to all these random sites. It was actually a crowded field back then. HBO had a site [This Just In], NBC had Dot Comedy, and there was Super Deluxe and College Humor. Most of them spent money, and you couldn’t really make money on the internet yet. So we just treated it like, “We can’t spend anything, so let’s try to make cool stuff.”

ADAM McKAY

In those first months, our job was just not to let the site shrivel and die. People were uploading stuff, and a lot of it was just junk—someone in their bedroom, doing a voice that wasn’t that funny. But some of it would actually be kind of surprisingly good. And we were shooting videos ourselves. Sometimes we’d just go, “I have an idea: Let’s just do a bit where I’m a grown-up who wants to, like, be a child again. And then I’m stuck in the tree and I’m afraid.” And we went out the front door of our office, shot this video, and put it up. There was such a hunger for this stuff—even a video like that, which is admittedly not the best video, would get, I dunno, 400,000 hits or something. We would start putting this stuff up, and then, because of “The Landlord,” people started calling us.

Though hardly a rough-and-tumble operation—not many startups get backers as big as CAA and Sequoia—Funny or Die did spend its early years in of a series of glamour-free bungalows in Hollywood, with a small full-time staff and an ever-growing team of work-for-hire comedians, many of whom had gotten their start performing at the Upright Citizens Brigade theaters in New York and Los Angeles. Thanks to the success of “The Landlord,” which today has 85 million views, Funny or Die was able to lure in stars like Eva Longoria, Don Cheadle, and Justin Bieber to appear in videos.

OWEN BURKE (writer-director-producer)

We would just yell across the windows to each other and throw stuff at each other, to the dismay of all of the other production companies. And we were always shooting something. There weren’t any real rules—nothing was established about what to make or how. It was, “Just make it.”

LAUREN PALMIGIANO

We had one camera and a boom mic, and we bought our own props and held the boom mic for our own shoots. At one point, the COO called me in and was like, “Can you send me some budgets for those videos you’re shooting?” We were just like, “Budgets? I went to Hollywood Toy and Costume and spent 11 bucks on a hat—is that what you want?”

JAKE SZYMANSKI

We had so few people working on this thing that I would get up at 4 every morning—after being up late editing—and manually change what videos were on the homepage.

JENNIE PIERSON (writer-performer)

At the beginning it was like, “Come do this video and you’ll get a free meal.” That was exciting, because anything that’s free, especially food, was very exciting at the time. Stuff had to get pulled together really fast—people would pick an idea, and then it would be shot in the next day or two. And at the beginning there was a lot more weirder and more abstract stuff: “OK, what do we all find funny?”

SCOTT GAIRDNER

Katie Couric was doing a story about Funny or Die. She interviewed me and asked, “What are you doing here?” And my reply was, “I’m PhotoShopping Tron helmets onto these Fraggles,” which is what I was literally doing at that moment. She didn’t seem to understand what that meant.

LAUREN PALMIGIANO

One of the company’s favorite videos is called “Stairs,” which is just Funny or Die’s Ryan Perez falling down steps. The world didn’t care about that video, but we were all like, “Yeah!” Usually everyone else helped you pitch your idea and helped you write jokes. That’s how bare-bones it was at first—just some goofballs shooting sketches. And then, over time, we had to get a little more organized. When Mike Farah came on, he gave us some Hollywood know-how.

MIKE FARAH (current CEO; producer and president of production, 2008–2015)

I’d been working at a production company, and my job ended during the 2007–2008 writer’s strike. I’d met a lot of comedians at UCB, and I started producing short-form comedy videos because there were no other jobs available. You had the strike, you had digital filmmaking being cheaper and easier to access, and you had YouTube.

Within a year, with comedy videos bringing in eight-figure view counts, the company launched noncomedy sites, hoping that the Funny or Die formula—big names + good videos + crowdsourced meritocracy = gold—could work in other arenas. But not everything stuck.

DICK GLOVER (CEO of Funny or Die, 2008–2012)

At the time, the mission wasn’t just Funny or Die, it was a model: User-generated content plus a voting mechanism plus celebrity shareholders who were vested in its growth. We were going to try to put that chemistry together with other topics. We got Tony Hawk to do an action sports thing called Shred or Die. We did a deal with Tom Colicchio, one of the top chefs on TV, to do a thing called Eat, Drink, or Die. We had Pwn or Die. Others were being developed—we were looking at weddings and pets and negotiating deals with people.

ADAM McKAY

We weren’t wild about all the other sites. They were saying, “No, no, this can work.” And when they put them in place I was like, “No. There’s no appetite for this.” I think everyone kind of realized that we’d extended the company too far.

DICK GLOVER

Then the fall of 2008 hit. Sequoia Capital called a mandatory meeting—all the CEOs of everyone in their portfolio companies had to be there. They begin a presentation, and the first slide was a tombstone that said, “RIP: Good Times.” Then they proceeded to have a presentation about how horrible the economy was. I literally had to keep myself from throwing up. I went, “Holy fuck.”

MARK KVAMME

Dick said, “We’ve got to live.” I mean, that company would not exist now if he hadn’t reduced expenses.

DICK GLOVER

We cut 30 or 40 percent of the cost out of the company and decided to focus on the one thing we were really good at: comedy.

In August 2008, just as the economy was cratering, FoD produced a last-minute sketch that would land headlines around the world—and solidify the company’s rep as the place for celebs willing to make a statement.

OWEN BURKE

The Paris Hilton video is the one that changed everything for Funny or Die. We moved from making small videos for ourselves to realizing, “We can have a huge platform.”

JAKE SZYMANSKI

John McCain had used an image of Paris Hilton in one of his campaign ads, implying Obama only cares about celebrity. And McKay had a great idea: “We need Paris Hilton to respond with her own campaign ad.”

ADAM McKAY

I was in my car—I think I was going to see my shrink—and was listening to the news on the radio, and right away I go, “She’s got to respond.” So I called her representatives, and her agent’s like, “I think she’d be interested in this.” I wrote the script really fast, and the next day we had Jake Syzmanski flying to meet her.

JAKE SZYMANSKI

They were like, “Take your camera and go to New York. We’ll send you our script when you get there.”

PARIS HILTON

I thought the writing was hilarious. We filmed it in my parents’ backyard—I remember trying to pick the perfect swimsuit—and did it in two takes. Everyone was very impressed with my memorization skills.

JAKE SZYMANSKI

The whole shoot took less than 45 minutes. I edited it on the plane, got back, stayed up all night to finish, and put it on the website the next morning. Paris, by the way, was very nice. She made me a turkey sandwich during the shoot.

PARIS HILTON

It was all over CNN and every news channel. I was getting calls from friends and family telling me how funny it was. It made me very happy to show that not only was I in on the joke, but that I also didn’t get this far being a dumb blonde.

ANDREW STEELE (creative director)

The Paris Hilton video is a crystallization of a kind of sensibility that I think was very much Funny or Die in the beginning: “Let’s do relevant topical comedy and see if we can find people interested in helping us make that in the Hollywood world.”

CHRIS HENCHY

The Paris video proved we didn’t need Will to have a big hit, and it was newsworthy. It always felt like we were doing the right thing when a comedy piece became a news story—you were at least shaking up the system a little bit.

Other topical sketches would follow, including 2008’s ambitious “Prop 8: The Musical”—starring Jack Black and Neil Patrick Harris, among others—and last year’s “Katy Perry Votes Naked.” The site’s mix of the political and pop-cultural, and its access to big stars, allowed Funny or Die to stake out space in what was suddenly becoming a crowded viral-video battlefield.

JON HAMM

There was no upside to doing it back then—it’s not like your manager was saying, “Oh, you should get on Funny or Die.” I think that actually exists now, where you can see people on there that are trying to boost their cred in some way.

MIKE FARAH

Back then it was a different world—no one else was making these kinds of videos. This was before Jimmy Fallon had “Lip Sync Battle” and before James Corden had “Carpool Karaoke.” Obviously, Lonely Island had started at SNL, but those were very scattered and premiered on TV.

SCOTT GAIRDNER

General meetings were set up with celebrities, and writers would go in there and pitch ideas. Your goal was to try to get Ke$ha or Kate Upton or whoever to make a video, but also you could sort of quietly plug along and make weird little side projects.

MIKE FARAH

I tried to make every video—even ones that took a few hours to produce—feel like a movie. So we had a publicist, we had a marketing team, and we made it really collaborative. We would work with these huge stars, and this thing that they made in half a day could be more impactful for them than a movie they spent a year on.

ANDREW STEELE

The celebrities sit in a room with a bunch of just-out-of-college kids, pitching these ideas. The best people are the ones who say, “I don’t know what this is, but let’s do it.”

LAUREN PALMIGIANO

I was in the meeting where we pitched Marion Cotillard, and there were about 30 ideas, including something called “Forehead Tittaes.” And I remember on her way out, she was like, “I really like ze fart and ze ‘Forehead Tittaes’ idea. I want to do something fun.” She wanted boobs on her head.

DASHIELL DRISCOLL (writer)

The first time Jeff Goldblum came in for a meeting, we all just hung out for what felt like 90 minutes. He talked extensively about his robe collection.

JENNIE PIERSON

We did a video in 2014 called “Sense of Smell” about a war veteran, played by Bryan Cranston, who comes back from the war claiming to have no sense of smell—and nobody believes him, and everybody’s been farting. And he goes on this big monologue about how he has no sense of smell, but now his sense of taste is heightened, so he’s been tasting all our farts. He was doing this monologue with all these euphemisms for farting, and he came up with one called Famous Anus Cookies. He improvised that. Also, he bought everybody ice cream from the ice cream truck that was passing by.

KRISTEN BELL

In 2014 they partnered with the Obama administration to disseminate important information that they didn’t feel young people were getting on the channels they were watching. I made one about minimum wage, where Mary Poppins says, “I cannot work for this. So you kids are on your own.” They take videos that we all made with our friends when we were kids, borrowing our dad’s camcorder, and make those kind of ideas watchable to a broader audience.

OWEN BURKE

A few years ago, Johnny Depp had come in to meet with Adam, so I pitched him The Art of the Deal, saying, “In 1988 Donald Trump wrote, directed, produced, and starred in his own TV movie.” And he was like, “Really?” And I said, “No, what I just told you was a lie. But we’re going to make it true by making this TV movie as if we unearthed it.” Once he said he’d do it, everyone at Funny or Die dove in. All the people that we had relationships with, we asked, “Will you come do this?”
It was shot in four days and cost about $250,000 because there were some logistics with his prosthetics team—and it was released the day after Trump won the New Hampshire primary, which was perfect timing. It’s so hard now to astonish anybody, because there’s such a glut of everyone being loud and crazy. So we let people catch up—Wait, what is this? Johnny Depp’s in this movie about Donald Trump?—and let the internet do the work of spreading the word.

MIKE FARAH

The celeb that got away was Oprah. We were probably 95 percent there to shoot with her the day the iPad came out—a video about the oPad, which was just her face telling you how to live your life. That would have been massive. But they had to cancel while we were on our way to Chicago.

ANDREW STEELE

In the beginning we were just gung ho on any celebrity, to the point where I think we were a parody sometimes. I remember we worked with … what was the name of the show with the woman with eight kids? We worked with the husband. Some of the writers might’ve thought it was fun because it was some sort of, like, cynical thing, but I never enjoyed that.

CHRIS HENCHY

There were moments where we started to dip away from topical stuff, and that’s when I felt the site started to get in a little worrisome area. Adam and Will and I all agree:
Do all the crazy stuff and the more bizarre stuff, but make sure you have a solid voice on the topical.

ADAM McKAY

Sometimes I became the annoying cranky uncle and would call the writers and go, “What are you doing? How do you guys not do something on this?”

Though celebrity- and headline-driven videos kept Funny or Die in the news—and helped usher us into an age of DIY-friendly celebrities—the site had also become a hub for oddball experimental sketches, both from the site’s creative teams and from users worldwide vying for attention from Funny or Die’s now-huge audience. Out of that daily deluge came some surprising successes—and some new comedy stars.

BILLY EICHNER (creator, Billy on the Street)

In the mid-aughts, I was making what are now known as man-on-the-street videos as segments for a live variety show that I was doing in New York. Then YouTube came along—but it was so early at the time, my then-managers and I were all thinking we should not put the videos on YouTube. Why would you give it away for free? And also, I didn’t want people to think that what they saw in the video was my whole act.

A few years later I made a video about all the summer movies that were opening up. Sex in the City 2 came out that Friday, and the critics destroyed it, so I went out and shot a little bit more footage about how angry I was at people who didn’t like Sex in the City 2. It went viral, and about a week later Funny or Die got in touch with me, saying, “Hey, we like these videos. Do you mind if we put them on our homepage?” And of course I thought, “Yeah, that would be amazing.” At that time, if you were someone like me, one of your goals was to get on the Funny or Die homepage—that was big.

Then Mike said, “Next time you’re in LA, we should talk.” And I saw that as an opportunity, so I lied to Mike and said, “Oh yeah, I’m actually going to be in LA at the end of the summer, so we should meet.” I didn’t want to seem desperate, so I bought a plane ticket that I could not afford. Eventually Mike set me up with a small production company to make a 10-minute version of how this game show, Billy on the Street, would work. And we got five pilot offers.

DEREK WATERS (cocreater, Drunk History)

I was doing Drunk History in 2007 on my own YouTube page, just for fun. And then—I don’t know how to politely say what happened—but Funny or Die would just post it as well. And I was like, “Oh, cool, this is awesome—it’s more promotion for Drunk History. I don’t even know these guys, and they’re posting my video.” When I started working with them, the casts and budgets went up a bit—I definitely don’t think I would have gotten Will Ferrell or John C. Reilly on my own—but I still wanted the show to feel homemade, and not all of a sudden so well produced that it took the comedy out of it. So it was great that Funny or Die didn’t have a big budget. [Laughs.]

BILLY EICHNER

I hold screenings at Funny or Die for Mike and other people there—nothing gets on the show if it screens poorly, no matter how much I might have loved it in theory. I trust their taste level and because they’re honest: They know not to laugh just to make me feel better. But I’m also annoyed, because their office is next to Oprah’s, and I’ve never seen her. My assistant has seen her twice. I’m very angry about it.

SCOTT GAIRDNER

In the early years, if something we made at Funny or Die got a million views, we would all stomp around our basement and celebrate to “You Make My Dreams Come True,” by Hall and Oates. We’d all shout, “Million views! Million views!” But we also started realizing all our favorite videos were in the Crypt, so it started to become kind of an honor—it indicated that you went for it and failed so spectacularly.

JENNIE PIERSON

At the very beginning the numbers mattered to me, but I quickly learned that I would lose my mind if I paid any attention to that. Once I had sent out a video and a family member responded with, “You know, I didn’t like it. I voted ‘Die.’” And that’s when I went, “All right, this doesn’t matter.”

One of the most popular Funny or Die series initially wasn’t meant for the web at all.
In 2011, Ferrell and writer-director Steele set off on a Midwestern road trip in order to film a series of Old Milwaukee beer ads that aired only in local markets, in some of the smallest cities in the country. It was among the company’s most visible for-hire branding efforts—a key source of the company’s revenue.

CHRIS BRUSS (president, digital)

We got this really crazy opportunity. Pabst was under new ownership, and they said, “Old Milwaukee’s a brand that we don’t know what to do with. The sales are going down. And if Funny or Die and Will Ferrell want carte blanche, you can do whatever you want.” That resulted in several of us getting in a minivan, staying in motels, and going from Terre Haute, Indiana, to Davenport, Iowa, to Milwaukee, Wisconsin, over the course of three days and shooting dozens of little 30-second commercials. And we ran them only in the towns where we shot them, which turned it into a news story.

ANDREW STEELE

An element of surprise is important to this company; it’s how you break through the clutter. The Old Milwaukee ads was an idea that hit me because the world was no longer dependent on networks, and the distribution mechanism had broken down so much, you could put an ad in Lincoln, Nebraska, and pay $3,000 a spot—as opposed to Super Bowl rates—and get the same airplay for the same commercial. That was a fascinating viral thing to try to do. And with Will, you can see the glint in his eyes when he sees a different approach to something or a surprise. It just excites him.

WILL FERRELL

We didn’t want it to get out on social media, so we were dashing in and out. One of the spots was in an intersection in Terre Haute called the Crossroads of America. I’d step out in traffic and begin talking as people slowly started to gather and wonder what I was doing in their town. We only got a few takes before a news crew showed up, and I hopped in our van and drove off. Sure enough, on their local news, there was a story asking whether I was in town or not and wondering why.

On January 4, 2008, Funny or Die premiered the first installment of Between Two Ferns, a talk-show-slash-awkward-confrontation hosted by Zach Galifianakis. The comedian, who would become a household name the following year with The Hangover, spent much of the next decade prodding and cajoling A-listers like Brad Pitt, Charlize Theron, and even the 44th president of the United States.

ZACH GALIFIANAKIS (host, Between Two Ferns)

I’ve always had this fantasy of subverting the very fake celebrity interview, because I had a very eye-rolly attitude toward Hollywood in the first place. I had a talk show [VH1’s Late World With Zach], but I never quite got to do with it what I wanted—it just wasn’t the right place. I was fantasizing about doing it again, and the context of a cable-access show made sense. So I just told Scott to get two ferns, a poorly lit set, and an actor. And then it’ll be pretty easy to do.

SCOTT AUKERMAN (cowriter-director, Between Two Ferns)

We shot the first episode with Michael Cera for a sketch show I was filming, in the basement of where my office was at the time. It was just us and the camerapeople, and Zach and Michael were improvising while we were watching on a monitor and shouting out ideas. For that one, there were no written jokes—it was just us trying a bunch of stuff.
It never aired on TV, so we reached out to one of our friends who was a producer at Funny or Die—which was pretty small at the time—and said, “Hey, do you mind if we put up this video?” We didn’t even know how it worked.

Funny or Die eventually became the home for Ferns, which has aired more than 20 episodes in the past decade.

DREW ANZTIS

It was filmed out back in the Shed—we’d set it up as a little soundstage. It was disgusting. You could smell the rats. We had celebrities coming into this little shit hole. I remember Jon Hamm being there and just sweating his ass off but being so cool about it.

ZACH GALIFIANAKIS

There’s a part of me that gets giddy inside when I know there’s a question that—even though guests know what they’re in for—it still can be offensive. So you try to strike the balance of not being really offensive but making it offensive. There are a lot of trash edits, because I can’t stop laughing—not because I think that the question is funny, but because the situation itself is so bizarre. It’s just this rude version of myself that I feel like the entertainment business kind of needs.

SCOTT AUKERMAN

When we’re improvising a lot, it’ll last a couple of hours. The longest was Bruce Willis. We had a fire stunt, so that one took a good four or five hours, and he was a great sport about it. We filmed that one back-to-back with Sean Penn. That was a very, very long day. Zach really wanted to do his brother character, Seth Galifianakis, so he had to shave his beard right after Bruce Willis and keep the mustache. I don’t think Sean Penn knew that Zach was going to be playing his brother in it. He thought he was just going to get regular Zach.

“SETH GALIFIANAKIS” (to Sean Penn in a 2010 episode)

This country boy right here is not really intimidated; I’ll follow you home tonight.

SEAN PENN (to “Seth Galifianakis,” on a 2010 episode of Between Two Ferns)

I’ll knock you the fuck out right in your chair.

ZACH GALIFIANAKIS

You don’t always know how much you can get away with. [Laughs.] I thought Sean was really mad. But I think we went and got a snack afterward. And they’ve all been really ecstatically fun. I don’t like to talk about behind-the-scenes stuff, but there are some really odd pieces of history that I have from a couple of shoots. One of them is a piece of underwear. I won’t go into details.

SCOTT AUKERMAN

At a certain point, we were talking about doing Ferns as a television show with a certain network, and we got the most insane offer I’d ever seen—I don’t mean moneywise as much as I mean freedomwise. And Zach, I think, at the time seemed kind of overwhelmed by everything that was happening—he may have been doing Hangover 2 at the time—and it just really seemed like too much to put a television series on his plate as well.
That’s been the MO that we’ve had the entire time: When it starts feeling like there’s too much pressure, we try to take a step back and remind ourselves that doing them is all about having fun. When they become too much like a job, when tensions start to run high on it, it’s because outside forces come into play—like if you have a star who will only do it upon the condition that they have final cut or who wants to see it before it comes out and give their opinion.

In 2014, Ferns landed its first political guest, when President Obama made an appearance to promote the Affordable Care Act. Hillary Clinton would follow two years later.

BRAD JENKINS (executive producer, DC office)

I was at the White House for almost four years in Valerie Jarrett’s office. When the Healthcare.gov website went down in late 2013, it took two months to fix. So while the site was down, our team was trying to figure out: “How are we going to reintroduce this to the public?” And Funny or Die had this very unique history. There was no other company that we could really point to that had those sort of political-impact videos and that also had this massive distribution network. Mike Farah had sent over the demographic breakdown of the people who watch Funny or Die videos and it skewed the exact demographic—male, with 80 percent of the audience between 18 and 34—that we were going after.

ZACH GALIFIANAKIS

I think it’s weird that politicians have to go on Between Two Ferns. It’s a sad state.

BRAD JENKINS

On the day of filming Obama, we had lunch in the West Wing mess, and Zach couldn’t get over the fact that the dessert in the West Wing mess was called Chocolate Freedom.

SCOTT AUKERMAN

Before filming, Zach and I were in the Map Room at the White House, next door to where we shot, which has all these maps with sort of those pushpins and yarn things like detailing troop positions for World War I and stuff. So we’re looking at these and Zach is sitting on a chair, and the guy in charge of the White House rooms comes in and tears into Zach and tells him that he’s sitting on a chair that’s an antique from Abraham Lincoln. Zach is like, “Oh, sorry, sorry.”
So we all get up and stand in the middle of the room, and then we’re talking about the video, and then the guy comes back in—and somehow, naturally, we had all sat back down in these chairs. [Laughs.] And he’s like, “Get out of these chairs!” And I don’t know how this happened, but someone broke this glass teleprompter, and it shattered all over this room of the White House, and the president was 45 minutes away or something, so that was a big hassle. His people were just like, “What have we got ourselves into?”

BRAD JENKINS

We were all very quiet waiting for the president to come in. He just, like, jumped into the room. He’s like, “Ferns! Ferns! Let’s do this.” That video, in many ways, helped save the first year of enrollment for Obamacare. It changed the game in Washington—and also the game in the White House. Before that video launched—I wouldn’t call the White House risk-averse, but I think that they played it safe—the most controversial thing the president was willing to do was maybe go on a late-night talk show.

SCOTT AUKERMAN

Zach always really wanted the mystery to be kept intact. For the Hillary Clinton one, we actually had to sneak him in, because there was tons of press around. I was a little worried that someone was going to find out—someone had actually tweeted that they saw the two of us on an airplane together, going to New York.
We told Mrs. Clinton’s team, “It would be great if we could do this like we normally do them—which is improvised.” And somehow they went along with it. There were a few lines here and there. Out of the hour that we spent shooting it, maybe five minutes of it was scripted; we knocked it all off at the top, and then she and Zach just improvised for 50 minutes.

ZACH GALIFIANAKIS

I was hesitant to do the Hillary one. I was a Bernie guy first, and then when it was she and Trump, the stakes were too high. I think there was an exchange with her representatives like, “You can’t bring up the emails.” And then it was like, “Well, then what’s the point?” You have to be open to making fun of yourself—which, in the long run, can be very endearing.
With the Hillary one, there was one bit we had to edit out because it was too long. I was like, “Oh, we have a faxed question from one of our viewers.” So Hillary Clinton had to wait for this long fax question to come through. And there was just the noise of the fax machine while I was trying to make small talk with her. That was probably the happiest I’ve been performing in a long time. It was just so ridiculous that I’m having small talk with a very high-profile leader, and it gives me joy when those two worlds can kind of dance with each other.
But I did try to get her to say the punch line about Donald Trump’s “white-power tie.” She said, “It would be better if you did it.”