The Inside Story of Derrick Comedy, the College Dudes Who Changed the Web Forever

In the late 2000s, Donald Glover’s now-legendary video team were the best thing on YouTube. They were just the last to realize it

For many of us, the founding of Derrick Comedy’s YouTube channel in 2006 was the beginning of the internet. The template is practically biblical at this point: Three college dudes filming no-budget short-form sketches in messy dorm rooms and commandeered lecture halls, for an audience of either everyone or no one. If they couldn’t win fortune, fame and creative autonomy, they’d at least settle for something fun to do on a Saturday afternoon. 

The principal members — D.C. Pierson, Dominic Dierkes, director Dan Eckman, producer Meggie McFadden and an impossibly fresh-faced Donald Glover — have all charted their own paths in the entertainment industry in the decade since Derrick folded in 2010. But for their millennial fans — the generation that served as social media’s first test case in the mid-2000s — their oeuvre pierced through each of our digital coming-of-age stories. 

For a brief period of time, the group was the best thing on the internet. Derrick was just the last to realize it. “We were completely unaware that there was even a YouTube community. We thought of it more of a place to post things, to drum up interest in our stuff,” says Eckman, 36, who still works as a director. “Like, maybe that would get someone to write about us on CollegeHumor. We never saw YouTube for what it really was. We didn’t realize that being a YouTuber was a thing.”

You’ve probably seen most of Derrick’s greatest hits, even if you don’t realize it. They were embedded into countless Myspace pages and ancient Facebook walls. In fact, if you’re in your late 20s or early 30s, there is a good chance a Derrick Comedy sketch was the first video you ever shared on the internet. There’s “Opposite Day,” an improv game turned into a skit, performed with a precision of language that rivaled any writer’s room in the country. There’s “New Bike,” which injected a surprising amount of heart into a joke about patricide. Go back and watch “Hip Hop,” which could be read as the beginning of the Childish Gambino persona, or the whirlwind, Radiohead-centric “Girls Are Not to Be Trusted,” and the heavy dose of Mr. Show DNA in its veins. 

Today, the comments on those videos reverberate with a wistful, web-addled sentimentality, each of us remembering the overcrowded computer labs and candy-coated iMacs where we laughed and screamed at each month’s new video: “Shout out to 240p!” “I come back to this at least once a year. I was 12 when it came out. It’s still amazing.” “If Derrick Comedy was still active until now, it would probably be the biggest channel on YouTube.” What a joy it was, to believe that anything was possible with a video camera and the internet.

But the Derrick crew themselves are far more level-headed about their legacy. They can’t find it within themselves to be reverent. In fact, for most of Derrick’s run, they never understood how they were changing the world. Instead, the group looks back on those videos in the same way you and I recall our college years: a lot of sanguine, naive memories, with a few embarrassments in the margins. 

Derrick Comedy came together in the same way that comedy kids always join forces. Pierson, Glover and Dierkes worked together in another New York University sketch group called Hammerkatz, and quickly found themselves in each other’s orbit both creatively and socially. They splintered off into their own sect along with Eckman and McFadden, who weren’t performers, but were heavily invested in their own dreams: directing and producing, respectively. If there was a secret sauce to Derrick’s success, McFadden attributes it to the sheer amount of time they spent with one another. Everyone in the group took sketch comedy seriously — perhaps too seriously, as Pierson notes — but the rare, impeccably stupid ideas that fuel the art form’s classics tend to surface during bleary nights with those you trust most. If Derrick Comedy weren’t best friends, there probably wouldn’t have been a Derrick Comedy.

“We literally hung out all the time. When we weren’t making sketches, we were playing Street Fighter or Mario Kart. I have nostalgia for the way we were creating those sketches. Us just hanging out at 3 a.m. and having a weird idea,” says McFadden. “You can’t maintain that at a certain point in your life. It’s fun to think about how we were in the car, goofing around, making fun of shock-jock DJs and then we made a really weird sketch about shock-jock DJs.”

2006 was a time before influencer workshops, FitTea brand deals and Twitch streamers signing lucrative CAA deals. There were some sketch groups, like Smosh, that were beginning to become famous on YouTube, but Derrick was completely disconnected from any careerist goals. There was never any real hope that the internet could serve as a ground-zero starting point for the group, mostly because that sort of infrastructure didn’t yet exist in their era. The only reason they started a YouTube channel, says Dierkes, was that it seemed like an effective home for the sketches they were already writing and performing on stage. Nothing more, nothing less. A means to an end. If someone saw “Keyboard Kid” and decided to buy a ticket to one of their UCB dates, that alone would be the experiment fulfilled.

“We never thought of ourselves as a YouTube sketch group. I don’t know if anyone did at the time. For most of the life of Derrick we would joke around about when we were going to get paid our ‘YouTube dollars’ not knowing that was where things were headed,” he says. “At the time, most sketch groups we knew weren’t putting videos online. We felt a little ahead of the curve there, but we never invested much in trying to figure out how to maximize our reach on YouTube. Many groups that started after us completely surpassed us in that regard.”

Pierson, in particular, recalls the ingenue way he claimed the YouTube domain. The group had already settled on a name: Derrick was a play on how the other players, Donald, D.C. and Dominic, all had first names that started with the letter D. (And no, he doesn’t know why it’s spelled “Derrick,” like an oil rig, instead of just “Derek.”) But the “Comedy” part, he says, was added to make sure that would-be viewers knew what to expect on the channel — like a prehistoric bit of SEO optimization, the sort of logic your mom might use for her bread-centric Instagram feed today. It is strange to imagine a group of college kids being so un-attuned to the shrewdness of digital self-promotion, but those are the pitfalls of getting famous on the internet, before the internet was the internet. 

“I wanted to let people know that this was ‘comedy’ just as a designation,” laughs Pierson. “It was just a way to understand what this is. YouTube was so new, so I felt like I needed to say, ‘This is comedy!’”

The group uploaded its first video, a hallucinogenic send-up of the theme song from Fraggle Rock, on April 16, 2006. A young Glover adopts a wild-eyed Woodstock growl, and squeezes out a wrenching heartbreak anthem directed at Jim Henson’s finest creation. (Why don’t you return my phone calls, Fraggle Rock!”) That too was completely inauspicious. The group had a date in Atlanta — booked by Glover’s former drama teacher — and they wanted to play a few shorts in the breaks between their sketches. (In addition to Fraggle Rock, Derrick produced parodies of G.I. Joe, Bananas in Pajamas and the Care Bears.) YouTube was simply the best place to host the clips. After all, it was free. 

“It was extremely Donald, for the lack of a better term,” says Pierson. “We were joking around about that alternative theme song bit, and I turned around and overnight, he’s already recorded and produced like, six of them.”

But Derrick Comedy didn’t hit the internet mainstream until a few months later, with the release of the eight-minute opus, “Bro Rape,” a faux-Dateline investigation into fratty dudes sexually exploiting other dudes. It was textbook Derrick — lo-fi and crude, but written with a diligent perfectionism and graciously acted. Glover commits all the way to his role as a ruthless sexual predator, sitting in witness protection in front of a peeling Family Guy poster. Dierkes is sublime as a buttoned-up Chris Hansen stand-in, and halfway through the runtime, a young, curly-headed Bobby Moynihan splashes through the frame, and predicts the decade’s worth of psychotic breakdowns he’d have on SNL. “Bro Rape” has accumulated over 11 million views, more than any other video on the channel. Fair or not, Derrick’s marquee sketch will always be a rape joke. 

Eckman, of course, admits that in 2020, and within a much more responsible comedy environment, the idea of directing an extended sexual assault parody — no matter how preposterous the context might be — wouldn’t even occur to him. “You look back on yourself, and how can you not cringe? We’ve all grown a lot as people and artists,” he tells me. “A lot of that stuff we wouldn’t do today. Not out of fear of backlash, it’s just not where our heads are at.”

“Bro Rape,” for what it’s worth, wasn’t as cruel as some of the other comedy instincts of the mid-2000s. Derrick Comedy wasn’t edgy. They often prioritized a certain nerdy earnestness in their comedy sensibilities, and many of their characters were surprisingly sympathetic figures. That said, there are plenty of other items in the catalogue that are, well, of their time. In “Spelling Bee,” we watch a series of petrified middle school students struggle through the exact same word — a highly offensive portmanteau of the N-word and F-word. “Foreigner” flies way too close to the sun with a bad, uncomfortable domestic violence conceit, and most infamous of all is probably “Blowjob Girl,” about a sadistic girlfriend who insists on using her teeth during fellatio. 

That actress was Ellie Kemper, most well-known for her time on The Office and Bridesmaids, and who disavowed the sketch later in her career. “I wish that I hadn’t done it, even though I know that it’s a joke,” she told the A.V. Club in 2010. “I hate that it got sort of big, because I don’t think that it’s that funny and I don’t want that to be the epitome of my work.”

Pierson, who co-starred with Kemper in “Blowjob Girl,” says the two have since spoken about her regrets, and tells me he completely understands where she’s coming from. After all, nobody in Derrick ever expected the videos to remain in the public eye for decades. They all have some insensitive moments locked up in the YouTube vault. That’s just another of the weird fallouts from blowing up during senior year of college.

“She wasn’t thrilled that she would get recognized from that. That’s always made sense to me,” he says. “You don’t think that when you’re in the local improv scene, and you’re going to be in your friends’ internet video and getting paid $100 for it, that that’s the thing that will follow you around. I’m very sympathetic to that.”

Truthfully, Pierson says that throughout his time on YouTube, he never felt authentically famous. The internet zeitgeist and his day-to-day life never intersected, and the potential resume implications of, say, an overworked blowjob sketch didn’t materialize in his world. The one exception he remembers happened when he and his family were on vacation together. He was walking out of a restaurant and a teenager was coming the other way. “He said like, ‘Are you from Derrick?’” says Pierson. “I remember my dad being really stoked about that, that someone would recognize me from the videos we were making.”

Each of the members in the group recall a similar experience. YouTube fame, at its absolute apex in 2006, typically manifested with little more than some extended eye contact on campus. There was no special treatment, no endorsements and not much money. Influencership is big business now, but Derrick hit its apogee long before institutions like VidCon established itself in L.A. In fact, nobody in the group remembers doing much, if any, of the parasocial groundwork of relatability. They didn’t reply to comments, conduct fan Q-and-As or celebrate subscriber milestones. In fact, throughout their legendary run on the platform, Derrick was always in character. We never got to see the real D.C., Dominic or Donald. Those three may have created internet sketch comedy as we understand it, but some of the hustle that comes with those responsibilities was picked up by a future generation.

“We knew the YouTube channel had a lot of views, but it’s not like those people were mobbing us in the street,” says Dierkes. “We didn’t have the type of YouTube following that you see today where these YouTube stars announce their location and then thousands of teens show up. Our ‘fame’ was more on the level of small pockets of comedy nerds across the country.”

But if there was one ambition at the center of Derrick’s success, it was to make a movie. Everyone I spoke to made that clear. If Derrick could transmute their heat to a feature film, the YouTube channel served its purpose. McFadden remembers that in 2007, the group linked up with a few managers and talent agencies, and she booked an itinerary for the boys to pitch a script to a series of studio bigwigs in L.A. Pierson remembers that trip being alternatively stressful and surreal. This was a time before Waze, which meant that a gang of college kids were doing their best to navigate Burbank with nothing but city maps and guile. 

More importantly, they didn’t technically have a script ready yet. Derrick had an idea — a movie called Picked On, described as a mashup between The Warriors and Revenge of the Nerds — but the group was still polishing and rewriting the pitch in their musty hotel rooms between meetings. They were operating off of momentum rather than substance, remembers Pierson. Nobody can be fully prepared for their first sit-down with a powerbroker, but three dudes with a lo-fi web series weren’t the typical pitchmen in the mid-2000s. They tried to wing it, which is respectable as hell, but also fundamentally doomed.

“I remember this one guy got up and started watching our videos, while expecting us to continue the meeting and keep talking about our idea, which I remember being pretty mortified by,” says Pierson, adding that it quickly became clear to the group that they needed to think things through a little bit more.

Derrick Comedy did eventually get their movie — in the most Derrick Comedy way possible. Mystery Team had a much different origin story than the failed Picked On tour. Pierson, Glover and Dierkes spent ages perfecting every gag in the screenplay, in the same way they used to bleed over the jokes in their YouTube videos, and the group eschewed the Hollywood model entirely. Instead, Derrick went super-indie, with a sub-million budget and a countrywide expedition promoting the film. Mystery Team released at Sundance on January 17, 2009, and netted about $90,000 in total. 

A self-made film credit is nothing to sneeze at, but some of the Derrick coterie feel like the movie didn’t get a fair shake. In many ways, 2009 was a terrible juncture to release a tiny comedy. The country was in the throes of the Great Recession, and there was no Netflix, Hulu or Amazon to sop up the loose ends and weird ideas that tend to be ignored by major studios. Mystery Team was a film without a nation. The deck was stacked against it. “As much as we were in the right place and the right time with YouTube, we were in the wrong place at the wrong time with the distribution of Mystery Team,” says Eckman. “It fell short of our hopes for it. But I’m really proud that people are still out there finding it and watching it.”

Eckman is right. Mystery Team has become something of a demi-cult classic in the years since. If nothing else, it’s a remarkable archaeological exhibition of that generation of New York comedy. Obviously it features Donald Glover right before his career went white-hot, but it’s also Aubrey Plaza’s first feature film role. Jon Daly shows up for a while, as does Kemper, John Lutz and the immortal Moynihan. Pierson jokes that, in some ways, this is the Derrick Comedy legacy: serving as the Rick Dalton meme for early UCB royalty. 

But Mystery Team also served as the swan song for the group. Derrick uploaded one more sketch — a typically bizarre Thomas Jefferson character bit on May 26, 2010 — and the three principle members disappeared into the ether as quickly and as ambiguously as they arrived. They continued to perform in a weekly improv show in L.A. for years afterwards, but as Dierkes puts it, the dynamic was never going to be the same. 

No one can remember a formal, throw-in-the-towel conversation; instead, the end of Derrick was just a symptom of their own diverse careers. Glover had just been recruited by Tina Fey to work on 30 Rock. A few years later, he was one of the most famous people in the world. Pierson published his first book, The Boy Who Couldn’t Sleep and Never Had To, in early 2010. And Dierkes was about to embark on a tour of L.A. writers’ rooms, contributing to everything from Workaholics to The Mick. Derrick Comedy was always intended to be a small piece of their individual careers. They weren’t going to stick around YouTube forever. After all, they were never YouTubers to begin with.

There is perhaps an alternative timeline where Mystery Team blows up, and Derrick Comedy sticks together for a little while longer. Maybe there’s another movie, or a TV show, bringing Derrick’s dynamite chemistry to the global mainstream. But Pierson doesn’t feel like he missed an opportunity. He finds nothing unconsummated about Derrick’s moment in the spotlight. In fact, he thinks there’s something kinda satisfying about the accidental symmetry of the group’s run; arriving fully formed out of the early internet’s primordial soup, climbing an unlikely ladder until they were allowed to put their names on a film. And then they flamed out. They dropped the mic and slipped out the back door, never to be seen again. That’s how they got famous, and that’s how they broke up.

And yet, despite the flippancy of the cast, it’s impossible to fully quantify the influence Derrick had on all the kids mesmerized by the first wave of YouTube. Personally, I recall being stupefied by the newfound implications of their success. If the funniest thing on the internet was being made by the kids next door, then gatekeepers like NBC and Comedy Central were firmly sundered. I could be famous by tomorrow afternoon. That is a powerful gift to offer any young person. 

“[Those videos] are definitely some stupid stuff we did in college, but I’m extremely proud of what Derrick accomplished as a group,” Dierkes concludes. “I’m most gratified when someone tells me that Derrick inspired them to find their way into comedy or to pick up a camera and make some sketches. If that’s the main legacy of Derrick, that we demystified the process of shooting sketches and putting them online, then I’m totally happy with that.”