Ten years ago this year, Derek Waters became one of the Founding Fathers of DIY internet comedy. All he had to do was invite a shitfaced narrator to recount Aarron Burr and Alexander Hamilton’s famous rivalry. Michael Cera (as Hamilton) and Jake Johnson (as Burr) perfectly choreographed a reenactment to every word, burp, and drunken malapropism while wearing anachronistic costumes and props. Waters threw the sketch up on a nascent Funny or Die and an unregulated YouTube, and Drunk History was born. The rest was, well, history.
Four seasons on Comedy Central and an Emmy win later, Waters is now a household name, and Drunk History’s blossomed from niche sketch comedy web series to hilarious historical document. The series has pivoted towards highlighting the absurdity of historical erasure, with Waters confronting whitewashing head on. In a way, it’s become a subversive version of Schoolhouse Rock, finding that sweet spot where entertainment and learning collide while slyly calling out the ahistorical bullshit we were taught in school.
On November 28, Waters is gifting the world the very first Drunk History Christmas special. Washington crossing the Delaware, Charles Dickens fabricating the holiday spirit and Teddy Roosevelt’s complicated relationship with Christmas trees all get deconstructed through the comedic cloud of inebriation.
Waters sat down with VICE to talk about the special, what to expect from season five next year, and why inclusive storytelling is the only way to get history right.
VICE: Why did you decide to do a Christmas special after four seasons?
Derek Waters: I just wanted to do a fun episode. I approached it the same way I do our regular season stories, where we take the more serious stories from history—the ones that
make you wonder why we never learned them in school in the first place—and find that hook in the premise that could be retold in a funny way. There’s an episode in the upcoming season called “Civil Rights” which we didn’t take lightly. So for this Christmas special, we could be a bit looser with things like Washington crossing the Delaware. I never even knew that happened on Christmas [ Laughs].
What’s your process for matching your narrator and guest actors with a particular historical event?
I have a better grasp of which story would be great for a certain narrator more than which story would fit for a particular re-enactor. Phil Hendrie, who narrated the Charles Dickens’ segment for Colin Hanks, was the first person I thought of since it would require all those unique voices. I just kept picturing it being like a play where Phil Hendrie was voicing each character on stage. He was an easy thought.
Then there’s Rich Fulcher, who narrated the Teddy Roosevelt Christmas tree tale. I think that story is cute and when something’s too cute, I’m like, “Let’s get someone that can make it funny and insane. It’s a simple story and in Rich’s hands it gets crazier and crazier. Then I had Craig Ansette tell the George Washington story. I thought that story might not be as funny but I knew he would commit to getting drunk and making such an important moment in history so messed up.
Did you approach the material any differently this time around?
I directed all three parts of the Christmas special. My ultimate dream is that the show has a Waiting for Guffman quality, where people are trying really hard but for some reason, it’s just not going that well. In Guffman, it was due to talent, but with our show it’s because the narrator’s drunk. But the commitment is what punches through. That’s what I strive for: taking ridiculousness seriously and seeing how passionate these storytellers are. I always try to make sure it stays within that same tone without it trying to be too funny.
Did you challenge yourself in any new ways as a director from a technical standpoint?
With the “Christmas Carol” segment especially, I wanted it to feel like a play. I’ve never done that before, with all those different backdrops and shifting set pieces and trying to do the interstitial it was all in one stage. So that was a creative challenge for me. I never want to be complacent. But I still want the show to feel spontaneous and fun. A show that takes itself too seriously is something I am just not into.
A perfect example of that was the “Washington Crossing the Delaware” segment. That was all a real projection. At times I was like, “Man, is this starting to look a little too good?” [ Laughs] So I decided to make the rafts on ice cubes and have cheap-looking models. Some of the intentionally cheap production value should remind you that this is a comedy show. It’s important to me that it still has that homemade feeling.
When the narrator is shitfaced and telling the story, are you visualizing how each beat will play out in your head? How much do you nudge them to get a better narrative out of them?
I never say, “Hey, try saying it like this.” I don’t coach them at all. Rather, I will ask, “So what else is on the boat? What is that person doing in the background?” I just have them picture it for me. It’s more of me getting the details out of them. I’m like a drunken lion tamer.
Do you have any horror stories from when a narrator might have gotten too hammered?
A lot of people like to pick fights with me and get very aggressive. Luckily, most of them are my friends and so I know it’s the poison that I fed them that is yelling at me, not them. Being drunk and having someone tell you to repeat a story again and again is frustrating. It comes with the territory but it’s not that bad. That’s why I wouldn’t do it with random people. I don’t mind my friends yelling at me. But random drunk people? I don’t want to deal with that. I would go to sports bars if I wanted to do that.
Both Hollywood and our history books have a long, ugly tradition of whitewashing, which makes your dedication to inclusive storytelling and diverse casting feel even more urgent.
I have two responsibilities: to make you laugh and to make you learn something. Then, behind that, it’s how you do it. You have to do it the right way. No one wants to learn if they feel like they’re being told they have to learn something. But if you’re laughing, you’re secretly learning.
Now the show is at a point where I can get away with telling stories that you’re just blown away by, and legitimately frustrated that you didn’t learn in school. Last year we did the Stonewall riots with transgendered actresses Alexandra Grey and Trace Lysette playing Marsha P. Johnson and Slyvia Rivera. We did a story this upcoming season on the Section 504 sit-ins on the Rehabilitation Act, which paved the way for the Americans with Disabilities Act. So it was important that we had all actors with disabilities in the reenactments. That’s the only way you’re gonna be able to tell that story with full justice. It’s all about telling stories that have been silenced and swept under the rug by history and telling them in a new way. I just want to give every story the heart that it deserves.
What can we expect from the fifth season of Drunk History when it returns in January?
There’s so much. One episode called “Drunk Mystery,” I’m very excited about. Then there’s “Game Changers,” that has Questlove telling the history of how scratching was invented. Also the story of Nichelle Nichols from Star Trek, how she was going to leave Star Trek until a Trekkie told her that she can’t leave because she’s too important. That Trekkie turned out to be Martin Luther King, and he convinced her to stay on the show because she was the only black woman on TV that wasn’t playing a servant. So she stayed. She had TV’s first interracial kiss with William Shatner. It’s a really cool story. I play Shatner, not to brag. It’s a big season. I think the show’s still funny but the stories are the strongest they’ve ever been by far.