In the Comedy Central series Drunk History, a drunk comedian — gently guided by series co-creator and drinking buddy Derek Waters — tells a historical story, which in turn gets acted out with characters lip-syncing every one of the narrator’s sloshed words.
The whole thing started out in 2007 as a low–budget YouTube sketch, with Mark Gagliardi telling the story of Alexander Hamilton and Aaron Burr’s deadly duel after he had downed a bottle of Scotch. Fast-forward nine years, and Waters is shepherding an Emmy-nominated show that’s about to premiere its fourth season of booze-soaked storytelling.
I recently caught up with Waters by phone to talk about how Drunk History is made, what makes a good drunken storyteller, and returning to a Hamilton story with Tony-winning musical creator Lin-Manuel Miranda in a way that brought something new to a story he’s now told a thousand times over.
This interview has been lightly edited and condensed for clarity.
Caroline Framke: You’re four seasons into Drunk History now, so you’ve clearly found ways to keep it interesting for yourself.
Derek Waters: Somehow!
CF: Was there anything you knew you definitely didn’t or did want to do going into this season?
DW: There were so many stories in the past three seasons that I kind of felt were forced in because we needed a third story for a city-themed episode. So I didn’t want that to happen at all this season. The purpose and goal [of Drunk History] is that every story is in because it’s an amazing story, and we’ll figure out a way to tie it in.
CF: Did the themes come first, or did you figure out the themes as the stories came up?
DW: This season, the stories came first and then we figured it out. “Oh, those were all escape stories, let’s do one called ‘Escapes.’ Those people were all legends, let’s do one called ‘Legends.’”
It was fun, and if we do it again, I’d definitely go with themes first and then find the stories, because, uh, this was pretty hard. But I’m so proud of the stories we found this season.
CF: What’s the process of choosing the stories? Is it collaborative, or do the participants come to you with the stories they want to tell?
DW: Sometimes I know they’ve always loved a story or a certain historical figure that I have researchers look into. Sometimes I just pitch them types of stories. Most of the narrators I know pretty well, so I know the types of stories they like, and then I present them with three or four stories that we’re definitely going to do this season and let them pick which one of those that they really attach to.
This year, we have a story about Ella Fitzgerald and Marilyn Monroe’s friendship. It’s really great, and when I pitched it to potential narrator Tymberlee Hill, she was like, “Oh, I know this story! I have a picture of Marilyn and Ella in my room!” Those are cool moments. I love that.
That’s the goal. Narrators have to be people who are passionate about the story and are dying for more people to hear it.
CF: So what makes someone a particularly good storyteller, outside of passion?
DW: It’s a mixture of a couple different things … a strong voice of their own, a confident demeanor, and likability. If you don’t like the narrator, you’re not gonna give a shit about the story.
They have to be comfortable on camera. [It shouldn’t be] their first time drinking, and they should be smart. Intelligent. It sounds simple, but telling the beginning, middle, and end of a story is hard for certain people, and then you multiply that by alcohol and it’s very difficult.
They deserve all the credit in the world. There’d be no show without them.
CF: Being a likable drunk is also so much harder than it sounds.
DW: It’s very hard! Hard to like someone who can’t make sense. But that’s what I like — you’re kind of rooting for these people. “Oh, they’re struggling, but they’re gonna get through this!” And they always do.
CF: You’re basically the moderator, too.
DW: Yeah! I guess I’m a drunk whisperer, in a way. Drinking with them and knowing what to say and what not to say. I’ve learned a lot of patience. A lot of patience.
CF: When do you know that someone is at the right level of drunk to tell a story? Are there any tells?
DW: There are a couple. The first one is repeating something that you heard, like, 10 minutes ago. I’ll say, “You told me that already,” and they’ll go, “No, I didn’t.” And then you go, “Okay, here we go.”
Also, the brain won’t allow, like … like a VCR, you have the fast-forward, rewind, stop, and rewind functions. When I say, “All right, what happened before that?” and they say, “Well, he was born in. …” The drunk brain has a very hard time going backward one chapter. It likes to go back to the beginning.
What’s another one I’ve never said? It’s weird, I can kind of just tell! [laughs] Usually it’s just their demeanor, the way they’re talking to me. At first it’s really nice, like, “It’s so great being on this show!” Then it becomes, “FUCK YOU, DEREK!”
And then when they stop caring about the camera, too. Every human being in front of a camera is going to be playing to it for a little bit, but once that stops happening, it’s good.
I don’t want anyone trying to be funny. I want the premise of the comedy to be how they’re telling this story.
CF: It’s always kind of interesting to watch the people who try to make jokes still, but it’s almost always funnier when they’re just telling the story and ridiculous things come out.
DW: Yeah. But if they’re bad jokes and I can make fun of them, I usually keep those in. [laughs]
CF: Can you tell me a little bit more about how the Hamilton episode came together? I know Lin-Manuel Miranda was really excited about it.
DW: It was really a gift. I had heard that he wanted to do it and was a fan. I reached out about the possibility of doing Hamilton, and it was hard because he knew we had already done one; it was the very first one we did online.
I also just didn’t want him to feel like, “Oh, it’s the drunk musical.” I wanted to reiterate that this would be a completely different thing, and that I would want him to tell stuff he didn’t get to tell in the musical, and that it would be a whole episode. One story for a half-hour is bold, so I wanted to make sure we did it in a delicate and smart way.
Because that’s what I want to find: great stories told by people who are passionate about them. There’s no one more passionate about Hamilton than that young man.
CF: Was it difficult to make sure you got weirder and more obscure details from him? He’s told that story so many times, so to fill a half-hour, how did you both try to tell a story that we hadn’t heard before?
DW: Well, I don’t think he’s ever told it publicly and while drinking. I guess I just tried to treat it similarly to the other stories, humanizing these people and conveying why we need to know about this story, what was important about it, what we can learn from it.
I just let it happen. My goal all the time is to make people feel as comfortable as possible. We shot it at his parents’ house, so, you know, there’s nothing more comfortable than getting drunk at your parents’ house while they’re upstairs listening to you drunkenly yell about Hamilton.
CF: Did you know already that Aubrey Plaza and Alia Shawkat were going to play Hamilton and Burr? How did that casting come about?
DW: That took a little time, because we wanted to do something as an homage to the musical but not doing it exactly, with mixed races for everybody. Bokeem Woodbine (Fargo) does play George Washington, which is cool.
We just thought, “Why can’t they be women?” And Alia and Aubrey are just two of my favorites. They’re the best.
I just wanted it to be heartfelt and have you believe these two are Hamilton and Burr. They did an amazing job. Their performances are unbelievable.
CF: What makes someone good at reenacting the stories?
DW: I learned this recently with Busy Philipps, who was just so good it was mind-blowing. I asked her, “How are you so good at this?” and she was just like, “It’s ADR” [voiceover work actors sometimes do to fill in sound gaps].
Being able to lip-sync along with the narrator’s persona and how they speak, too. It’s a real specific skill that possibly they didn’t even know they had until they did it.
Basically, someone who’s taking every word as if it were Shakespeare when it comes out as drunk rambling. The more dramatic, the better. Ridiculousness taken seriously.
There are so many things that go into this show that it could fail real quickly if we didn’t get the best of the best — behind the camera, in front of the camera, everywhere.
CF: Was there anyone this season that you wished you could get to play a character and then it actually happened?
DW: I always wanted Tony Hale to play Buster Keaton. He looks like him, and obviously he plays Buster in Arrested Development. But what he did with that was just unbelievable.
And then there’s a Charlie Chaplin in the Buster Keaton story, and I was like, “Man, it would be really cool to see Billie Joe Armstrong of Green Day play that part.” It turns out that he said yes, and revealed to me that he’s been researching Chaplin for the past year. He’s obsessed with him.
That’s the kind of thing where it’s like, I’m just part of this ride. It’s above and beyond where it’s gone, when I thought it was going to be some one-time thing.
Season four of Drunk History premieres September 27 at 10:30 pm on Comedy Central. Previous episodes are currently available to stream on Hulu.