Jake and Amir’s Decade of Perfect Timing

Add it all up, and Jake and Amir’s videos have around one billion views. That’s a big number—a scary one. The amount of time people have spent watching two best friends fuck around in their office is, combined, longer than human civilisation has even existed. Why? Because they are very, very funny people.

The Jake and Amir story is interesting because it’s also the story of internet humour itself—their success runs parallel to the rise of outsider comedy online. They grew up with the web, but always stayed one step ahead of internet trends: CollegeHumor poster boys in the site’s infancy, Youtube class clowns before it became the behemoth it is today, then podcasters before every man and his dog were peddling Squarespace discounts. Today, Jake and Amir also own the podcast network Headgum, and have an LLC in their names.

The duo painted a picture of what comedic success could look like without TV, laying out a path that we’re going to see a whole bunch of their teenage fans follow in the years to come. So, before thousands of comedy clones emerge, we’re retracing the surprisingly influential footsteps of the internet’s original best friends that could.

Not Like Other Bros

In 2004, this is what Google looked like. This is what then one-year-old Myspace looked like. VICE wasn’t online. People used Lycos, and the most searched thing on Lycos was Janet Jackson’s Superbowl nip slip. When young people wanted to read something funny, a lot of them would go to CollegeHumor, where, in June 2004, the front page pushed a story called Dear Yahoo, I’m changing my homepage to Google.

Working on the internet at that time was still fairly radical, and it’s what both Jake and Amir did—it’s how they met. “I wrote freelance [for CollegeHumor] for free throughout college,” Amir tells us in a nice restaurant in Melbourne’s north. “The first article I wrote, I think, was things to do at a boring party to make it more lively. It was always lists and things like that.” A 2004 Amir joint called Countdown of Countdowns is a purported list of hot new VH1 countdowns. “Unless you’ve been living under a rock (or living under Iraq—Kuwait) you are very familiar with the myriad of countdowns VH1 has aired this year,” he wrote.

Jake joined the company as intern. “That was just me being proactive at 20. Actually the last time I ever was proactive. My first email to CollegeHumor was from my college paper. It was about cheap dating ideas you could do in New Haven, Connecticut. And [former CollegeHumor editor] Streeter wrote back like, ‘It’s a little specific for CollegeHumor, but if you make it more general we might be able to run it.’ So my first article was called The Lost Art of the First Date. I don’t recall how funny it was.”

Early Jake Hurwitz stories were about romance, in the broadest sense. Like this one from 2005: Assessing Risk: When and When Not to Beat It.

“We used to hide some stuff [by writing] under ‘CollegeHumor Staff’,” Jake remembers. Amir does too. “Oh! Wasn’t there a fake lady we used to write under? I remember she was really attractive, and whenever we wrote something that might be offensive we would be like, ‘Hey look, a lady wrote it, you can’t get that mad.’”

Jake admits now, “There’s plenty of stuff I’m ashamed of writing for CollegeHumor.” Still, they considered themselves outliers in a frat-bro world. “For a long time at CollegeHumor we were working to subvert bro culture by making extra bro-y jokes. I don’t think that made it any funnier. But in 2006, that was slightly forward thinking.”

That’s Not Terrible… It’ll Go Online Forever Now

While we can thank CollegeHumor for introducing Amir to Jake, the credit for the eponymous series that launched their careers (and a world of in-jokes, subreddits, fan clubs, and world tours) goes to Vimeo. “Vimeo and CollegeHumor and Busted Tees were all started by the same people,” Jake explains, “We shared an office with Vimeo, and there was a tonne of encouragement from them to create more user-generated content.” In 2004, Vimeo was just where founder Jakob Lodwick would dump videos of his friends, but the next year, it became a proto-YouTube—a place where anyone could upload something weird. Which is what Jake and Amir did.

Amir edited the first episode of Jake and Amir on iMovie. Jake was the CollegeHumor employee perpetually disgruntled by the never-ending verbal assaults of his petulant desk-mate, Amir. “We thought it was about as funny as you might think a Snapchat is these days,” Jake recalls. “Like, ‘Ha, that’s not terrible… it’ll go online forever now.’”

It didn’t feel like the start of something special at the time—”More of a business partnership,” according to Amir—but the Vimeo community was receptive enough for them to keep at it. “When we posted something on CollegeHumor, the first comment would be like ‘gay, fuck yourself.’ It was fine because we were paid to write and we enjoyed it, but we didn’t get the same thoughtful, positive feedback we got on Vimeo,” Jake says. “I think that’s testament to them: they had cultivated a really thoughtful audience.” (He cites Workshop and Monopoly as some of their best early, early videos).

As they continued shooting, the wordplay grew denser and more bizarre, and the library of Jake and Amir-isms became highly quotable. Fans still appear in the comments of actor Thomas Middleditch’s Instagram to shout “DOOBS,” (the name of a character he played years ago in Jake and Amir). A diehard fanbase coalesced around them, that phrasebook binding them especially tight. The pair never considered slowing the pace of the episodes, or making the jokes easier. “I truly believe the audience has always risen and elevated themselves to getting the jokes that we thought they might not,” Jake says. “You just have to trust people, and if they don’t get it, that’s fine.”

For the little thought they say went into Jake and Amir, it preempted some major digital trends. In a pre-Snapchat and pre-Vine world, the length of their first videos—just 60 seconds or so—was still unique. The pair would push to cram maximum narrative into the shortest clips, which ended up being the way the entire internet went. Eventually, CollegeHumor started paying them to do nothing but produce Jake and Amir.

In 2013, the duo started the podcast If I Were You, establishing a level of creative independence from CollegeHumor. Jake was the first to fantasise about leaving the site entirely. Amir says he liked the idea in theory, but he also liked having health insurance. So they stuck around as If I Were You started to take off, simultaneously producing some Jake and Amir fan favourites like Compost, Tinder, and Real Estate Agent.

In 2015, the big moment came: they announced the CollegeHumor series was over. In a real testament to the show, thousands of commenters grieved, all over YouTube. Considering how brutally the internet churns through content, and how quickly comedy trends get metabolised, it’s remarkable Jake and Amir avoided being a fad or a meme—let alone something people sincerely mourned.

From the beginning, CollegeHumor owned the Jake and Amir series, and by extension, the characters. Jake says they always knew CollegeHumor would keep the rights to show if they left, and that deal felt fair. “We weren’t in a position to be like ‘Hey, it’s ours!’ and go to court with [CollegeHumor’s parent company] IAC. They had been generous with the Jake and Amir contracts all along. We saw an opportunity to grow with the company that we wanted to take—or that Amir wanted to take, and convinced me to. But I was easy to convince.” So no, there’s no secret bad blood, but they don’t regret leaving when they did.

“I rush into most things,” Jake says. “I’ve moved in with a girlfriend too early, I’ve said ‘I love you’ before I meant it. With Amir, it felt like all the milestones were happening at the right moment… It always felt like we were really ready for the next step when we took it.”

Nerds Will Inherit the Earth

The next step was focusing their energies on If I Were You, an advice podcast which sees the pair answer fans’ personal quandaries with brutal honesty. A couple months into their post-CollegeHumor lives, they also started their own podcast network, Headgum. Again, their timing was perfect: the first season of Serial had wrapped earlier that the year, and the world was fast approaching peak podcast. Headgum now averages 100 million plays per month, and If I Were You alone averages one millions plays each month. “For whatever reason,” Jake says, “we’ve been really fortunate to say yes to the right things at the right time.”

Questions on If I Were You tend to come from teenage boys navigating relationships and sex for the first time. “We try to keep it balanced, but even when we answer more guy’s questions, at least we expose enough of those male patterns for female listeners to think about and comment on,” Jake explains.

The pair are well aware that most of their fans are at least a decade younger than them. “I always say that we’re like, the oldest millennials,” Amir explains. “15 to 34 is the area we play around in, and I’m 34, so I’m pretty comfortable with that.” Jake adds, “It’s way easier to answer questions for those kids because we were there, and we came out the other side. And I don’t think people tune into our show for thoughtful sombre advice anyway.”

That’s true. People tune in to feel like they’re part of Jake and Amir’s symbiotic, idiosyncratic friendship: with If I Were You, you’re always in on the inside jokes, and you don’t even have to contribute. Kids are also listening to hear from adults who genuinely seem to be having fun being, well, adults. For all the grown-ups that talk about how teenagers have it easy, or bemoan the jobs and mortgages and bills weighing down on them; there’s Jake and Amir, who talk about getting drunk on whiskey with their friends and travelling the world.

For the pair’s younger fans, who are probably a lot like Jake and Amir once were, it’s comforting to hear things will get better. Beyond the in-jokes—the Surge Dudes, the Gameboys—that’s the promise at the heart of If I Were You. “I think when you’re a nerd in high school you have to survive by believing your best years are ahead of you, you know, that nerds will inherit the earth,” Jake says. “It’s nice that we can be nerds that sort of embody that truth. We’re like a little beacon of hope for losers that are told they’re gonna be cool in ten years.”

“It’s hard to reconnect to that feeling, but I know that’s what brought me to CollegeHumor,” Jake tells us. “Twelve years ago I was depressed and lonely and sad in college, and that’s how I found CollegeHumor. Now I’m so far removed from that. I haven’t felt that way in so long, but I could be speaking to somebody who is feeling those things right now.”

A New Universe

At this point, it sounds like Jake and Amir have had a perfect career run. Every small thing they’re started has snowballed into a bigger, more successful thing. Except the TV show.

Deadline had once reported TBS were interested in an Ed Helms-produced Jake and Amir TV show, but it hadn’t progressed beyond a script. When Jake and Amir announced their CollegeHumor departure, distraught fans petitioned the network to get the wheels in motion on the project again with the Twitter-trending #GreenlightJakeandAmir campaign.

Ultimately, TBS said no, but their younger subsidiary truTV noticed the social media groundswell and commissioned the pilot. Through the podcast, Jake and Amir kept fans updated with breathless and elated accounts of what it was like to work with a real network. In the end, truTV didn’t order a full series either. So, in a nice twist of fate, they returned to Vimeo—who were again interested in original content—and made another web series, Lonely and Horny.

To Amir it felt better, or at least a little more fun, to go back online. “We had to make [the pilot] broad and silly and PG rated for TV, and when that didn’t work we were like, ‘Well let’s just do whatever we want for the internet, where we get no notes and can do scenes that would never work on television.’ Like the one where I have sex in a jacuzzi by myself.”

Jake and Amir have described Lonely and Horny as “a completely new universe,” but that doesn’t feel quite right. Amir’s Lonely and Horny character, Ruby Jade, was written to be flawed in almost all the same ways as Jake and Amir’s Amir. Watching Ruby interact with people outside of the exaggerated, hammy CollegeHumor universe, in Lonely and Horny’s fairly realistic imagining of LA, makes his absurdity register as more incongruous than hilarious. At the same time, Jake’s character Josh (another long-suffering straightman) is the most multifaceted role they’ve ever written—so Ruby Jade feels like he’s wound up in the wrong show. While Jake and Amir could have turned anyone into a fan, Lonely and Horny was better suited to people who were fans already.

Hardly a Consolation Prize

The internet is a young person’s medium, and you get the sense Jake and Amir, now in their thirties, are beginning to think long term. While television has proven to be the one beast the pair can’t tame, they’re still trying. “We’re pushing the ball forward as much as we can on things like TV and movies,” Jake says. “Writing for TV and movies was what I’ve always wanted to do, but those things are so slow, so it’s nice to have podcasting and digital stuff to stay in production.” Amir is eager for Headgum to create more original video content, growing into a fully-fledged production company.

The pair aren’t interested in getting into the writer’s room of an existing show—their whole career, they’ve had near-total creative control over what they’re producing. “The best example [of us doing TV] would be Streeter writing for SNL, and I don’t think I’d be good at that,” Amir says. “I could do some acting. We have very narrow wheelhouses though. I just can’t be serious or sincere.” Jake adds, “Nobody can play annoying like Amir, and nobody can play annoyed like me. Except for real actors.”

One of the more interesting things about Jake and Amir is how successfully they’ve leveraged their fame to work for them in real ways, like paying a mortgage. All these things that people never thought you could make serious money from—Ads on Youtube, Podcasts—those are the only ways Jake and Amir have ever made their money. The pair have created a whole new template for outsider success. Maybe TV will catch up one day too, and an original series will get off the ground. Maybe it won’t. Either way, a massive, dedicated online audience—Jake and Amir on CollegeHumor would, back in the day, draw the same amount of viewers as Keeping Up With the Kardashians does today—that’s hardly a consolation prize.

Yes Dude

Perhaps the most attractive part of Jake and Amir’s story is their friendship. By branding themselves as a two-for-one package, the duo are basically tied together forever—a daunting prospect for comedians less perfectly in sync. “We’ve gotten along for such a long time because we have the same comedy head,” Jake says. “We basically make the same jokes at the exact same time now.”

It’s hard not to envy a dynamic like that. “I don’t think we’ve ever had a fight where it felt like we were going to end the duo,” Jake says. “There was never a time where I was like, ‘we’ve got to figure this out or we’re going to lose everything we’ve worked for.’”

While they aren’t roommates anymore, they still hang out almost all the time. There’s been no seven year itch. “If I’m in LA and I’m not out with Amir, then I’m probably not out,” Jake says. “90% of the time Amir is more responsible than me and will check out early—”
“—but that magical 10%” Amir hints.
“There have been a couple of those and those are my fuckin’ favourite. I live for it every single time.”

Does this mean they’re… soulmates? Jake’s sure. “Yeah, he’s my soulmate. But he won’t say it.” Amir? “Definitely yes—if I believed in soulmates.”

Photography Tasha Tylee
Styling Issy Beech
Grooming Rob Povey using MAC