Meet the Filmmaker Behind Alt Comedy's Funniest Videos

I’ve been a fan of Whit Conway for years, though I didn’t know it until last spring, when I noticed his name in the credits of two beautiful short films released around the same time: Relaxing Old Footage with Joe Pera and Matt Barats' Here We Have Idaho, both of which he edited. As I wrote then, I loved the grand scope of these pieces, the way they paired their narrators’ whimsical monologues with a deeply serious, expansive visual language.

I quickly discovered these qualities are characteristic of Conway’s work. As a director, DP, and editor, he collaborates frequently with comedians like Joe Pera, Conner O’Malley, Carmen Christopher, John Reynolds, and others who operate in that same heightened-with-heart style. Conway came to New York by way of Chicago, where he studied at Second City and iO while working in commercial video production. Since moving east, he’s had a hand in some of the funniest indie web comedy of the last few years, like this month’s magical Conner O’Malley short “Endorphin Port.” He’s also worked on shows like SNL, Jimmy Kimmel Live!, The Late Show with Stephen Colbert, and Joe Pera Talks with You.

A few days ago I had the pleasure of speaking with Conway about his work. Below are some highlights from our conversation, edited and condensed for clarity. Whether you’re a comedy fan or a comedy worker, I think you’ll find plenty in here to chew on.

How would you describe the sort of work you're drawn to?

I am attracted to great partnerships and really good, unique ideas. I think I try and work open-mindedly with as many people as I can, if I have the time. In the past couple of years, I've started to get a little busier so I've had to be a little choosier with my collaborations. But my door is always open.

I definitely gravitate towards things that I feel take themselves seriously and can operate in multiple ways. I like to think that anything I try and make, I try and make it as seriously as possible, even if it's a very very silly idea.

What's exciting to me about a lot of the stuff you've made is that it's rooted in these very heightened performances, from people like Carmen or Conner or John Reynolds, that still feel very grounded and human.

To speak specifically about those guys, they are very aware of how they come across, and I think they also believe that the best thing they can do is take their performances really seriously. That's something that I feel like—I don't want to say it takes some time to learn, but I do think some earlier comedians might feel like, "Oh, I know I'm being a little bit funny now." They get that wink in their eye and it breaks the reality of the piece.

People like Carmen and John and Conner and so many other performers that I regularly collaborate with, I do feel like they just take it so seriously. It's in the seriousness of their emotion and the groundedness that the comedy really comes forward. Especially with the extremity of someone like Conner. And John, even—when we were doing Mayo Bubble, a lot of the stuff he's saying is insane. I mean, it's so out there, if you were to look at it on the page. But just to hear him do it, it works perfectly. And I believe that that is driven from him as just a really fantastic actor. He can put a little emotionality in a tone of voice, on a sad phone call, and you can believe pretty much anything coming out of his mouth.

There's also a slowness or a patience to the work that I don't see in a lot of other comedy these days, at least short-form comedy.

I started to not care about attention spans, I don't know, maybe five years ago. I just felt like everyone's chasing the shorter the better, and if you can get people to sit on a long zoom, there's something intriguing about it. I do think that you've gotta do that with intention. I hope that that comes across—there’s some reasoning to putting some of those slower moments in there. I would argue that it's about trying to build some tension so you can release it in some other way with some comedy or some laughter. It's setup and payoff—tension and release and emotionality. I think those are the three core things that I look at when I'm doing a project. The elements of those three core things have to be there, otherwise it feels like there's gonna be something missing.

Did you know early on in your career that they're what you're interested in? How did you come to develop them as your guideposts?

I think working with Joe Pera, and on his show, really helped hone my idea of what I really liked to see. And then just having some shorts work, and feeling like, "Oh, I finally found that thing after making 150 shorts." It is something that did evolve and I can't really put a pin on when, because I still do tons of work that I feel like, "Well, this isn't exactly my tone or style, but I'm happy to do it." I think that's sort of the necessary part of any career in this industry, the ability to flex. I mean, obviously everyone doesn't have to do that, but I think for me, I'm a dad, I have two kids, I have a mortgage, I gotta keep working. So I end up doing work that I'm like, "Oh you know, this might not be my exact tone or style, but I can see a value in it and/or it's a good paycheck." Which feels a little shilly to say, but I think it's true and somewhat necessary.

Yeah, I think it was just sort of what I started to react to. And then also learning how to direct by doing it, I think that was where that happened as well. And then just doing a ton of research in terms of watching comedy. Maybe about four or five years ago, I started to become more analytical about my own work, but also about watching work. And I did start to put those pieces together, that the stuff I reacted to more was the stuff that took itself seriously without winking. It was the stuff that felt believable and the stuff that pulled you in, in a more dramatic way. I think that helps the audience. By pulling them in, you get to lead them somewhere. If comedy is a part of that, if more dramatic moments are a part of that, that's okay. I think there's a lot of comedy to be had within that level of trying to play something more dramatically.

You mentioned learning the job by doing the job. Are there any pieces in particular you've worked on where you came out thinking, Yes, now I know how to do this thing?

Everything I did in Chicago was, “I’m gonna say yes to a project and try and figure out something to do, that I don't know how to do, and learn how to do it.” Even if that was lighting a room, which, don't watch my earlier work.

I do try—and this is something that I tell young filmmakers that reach out to me for advice—I sort of look at shorts as opportunities to experiment. Usually for me that's a production challenge. “Okay, I'm gonna shoot this one all locked down.” “I'm gonna shoot this one all handheld.” “I'm gonna move the camera and I'm gonna do deliberate camera moves or deliberate camera zooms here.” “Here is gonna be an Edgar Wright-style sort of speedy montage to get through this little moment of 10 shots. It'll be two seconds, it'll move really fast. How can I do that with no budget and no time?” That's really been very helpful in trying to learn how to put more tricks in your bag of tricks. Keep filling that bag up, because otherwise it just gets boring if you're doing the same thing over and over.

I think if you do a couple of failed projects, you start to see where things are failing too. That's the other thing. I definitely have at least 20, 25 shorts I've shot that I have never shown the world. And some of those will absolutely come out and some won’t. Some will never see the light of day. While that's a frustrating feeling, I always tell people that are sort of behind me that that's a better experiment than trying a feature before you're ready. I'm happy to do a day of filming, even spend some money, and if it never comes out, it's just a little bit of time.

How have you seen the landscape change for DIY web comedy?

It's sort of miraculous how many outlets there are right now. It feels like more content created than ever. It’s also harder to get people to watch stuff than ever, and also more ephemeral than ever. It's much harder to make something that feels like it lasts for a little while, because so much of what we consume these days feels like it's based around a very short-lived cycle. Even great work, even great films and TV feel like they just blow right by, and hopefully there's a couple of fans that get to glom onto them.

It's also just becoming so much more niche. I was thinking about this the other day—there's so many sects of everything. I think that's really good in that it feels like it's splintering and branching so much that there's truly gonna be, 100 years from now, just very individualized content that's for your eyes only, almost. If we keep going in this direction. It does feel like it's—from when I started, which was right at the beginning years of YouTube and right at the beginning of Funny or Die—in the 15 years or so that I've been an active content creator or filmmaker, that's already burst in a way. When I was at Second City and iO, in Chicago, everyone's going, "Oh, we got to the front page of Funny or Die." And I feel like kids now have no idea what that was like at that point, which was just—that initial buzz of, "Oh, people are watching my stuff."

It's changed so much. I think my attitude shifted a little while ago from that idea of, "I've gotta get people to watch my stuff" to "I just want to feel good about what I'm making." I've gotta entertain myself first and really be pulled into what I'm making. And if I feel good about it, then I'm gonna show other people, and hopefully they can get some enjoyment out of it.

That decision helped me focus towards why you said you called me, which was that emotional aspect. That was the stuff that I found really fun. Also I was finding performers that were doing that, and finding collaborations where that was more the goal. Going out with Carmen—we made some videos a bunch of years ago, one of our first collabs that we did, where he was like, "I'm housesitting in Connecticut. Just come on up, we'll make some videos." Then we just did that. We were up late one night making a video called "Up In Da Club," which is a really crazy insane video. And then the next morning we woke up and we were like, "Let's just make another one. This is a giant house. What if this is called Big Booty House?" He had this little song idea in mind. And that was one of the most fun things to shoot, because we were just having a great time in this house, thinking about the beats of the piece and how we could make them fun and insane.

The publications and the outlets, I think they'll always change. The way that I try and think about it is, well, they're always gonna change, but if I can keep entertaining myself, hopefully that will be a good north star for making stuff that hopefully people can connect with and enjoy.