Comedians Reveal the Hardest Joke to Write for Their Comedy Central Specials

Ryan O’Flanagan, Langston Kerman, and Emmy Blotnick. Photo: Courtesy of Comedy Central

Comedy Central Stand-Up Presents (previously known as Comedy Central Presents and The Half Hour) aired its first episode on December 1, 1998 and brought Wanda Sykes into the homes of America for the first time. The series has been in some way responsible for the rise of comedians including Mitch Hedberg, Chelsea Peretti, Greg Proops, Dave Attell, Jim Gaffigan, Patton Oswalt, Zach Galifianakis, and Mike Birbiglia, helping to break rising comics to a larger audience and showcasing a collection of unique voices and approaches season after season.

With the new batch of specials set to debut tonight, we gathered the nine stand-ups set to break big this season and asked them one question: What was the hardest joke to write for the taping?

Langston Kerman

There are two sections that took a lot of time. The closer probably took a huge amount of time because … I like the roll it goes on in terms of, like, talking about not doing drugs, and being this dweeb of a kid. Then I derail it by bringing race back into the conversation. It becomes this thing of, like, “Oh, we were all having a good time at the party, and then this motherfucker brought up current political issues.” So, I found myself in this space where it took a lot of care, and sort of thoughtful rebuilding on multiple occasions, to make sure that that joke could match the weight of what was building right before it. Then I’d say the material about white people not being able to write history certainly took a lot of care — it’s certainly the most righteous or militant position that I took in the special, and I wanted to make sure it wasn’t pushing people in a direction that made them feel alienated.

I rewrite a lot, but for me, the rewriting process is about identifying where the joke isn’t working, and making sure it does work where it should without compromising what I believe the most important part of what that material is. There are moments — and I find them all the time — but there are easier jokes to be made within the bits that I’m structuring. I could be writing this bit and easily go on a tangent or in a different direction that allows me not to make someone feel uncomfortable, or scared, or whatever that is.

I would like people to feel uncomfortable and scared, but I don’t want them to be overwhelmed by that discomfort. It’s figuring out a way to be like, “Okay, y’all aren’t laughing at that, but is it because you just are uncomfortable, or is it because the joke isn’t strong enough to help you through that discomfort?” I think that’s where a lot of the rewriting happens. I don’t want you to feel safe; I just want you to know that you don’t feel safe, but I don’t feel safe, so let’s not feel safe together.

Megan Gailey

My joke that I do about my grandmother’s Alzheimer’s took me years. I had a version of the joke you see now probably five years ago, and it just sort of never really took a shape that I liked. Too many people were sad when I was saying she had Alzheimer’s, and I was going, “Oh, well I don’t ever want to make anybody feel sad.” It kind of took a long time to figure out the pieces of how to make the joke funny, and work, and get people to like it.

Also, I told that joke in front of my mom now so many times, and it’s about her mother, and her mother having a very, very terrible disease. It’s also about her father not being a great husband to her mother. I was very worried about hurting my mom’s feelings, or feeling like I was putting her on blast. I mean, I called my dad an alcoholic on national television already, so I was like, “Jesus, am I just going to keep trashing everybody?” So, I think that joke was probably the hardest for me as a comic to put together, but is probably one of my favorite jokes I’ve ever written, because it feels so honest and true to what my experience with my grandmother was like.

I think the hardest thing was — and this is why it’s my longest joke — is because there were pieces of it that I kept adding. I kept going, “Oh, I really think this part of it is important for understanding the context of it.” I guess in some ways it was very precious to me, which is probably what made it hard. I really cared about it, and also don’t think Alzheimer’s is a joke. I do think that some people who have Alzheimer’s are very funny. So it was about striking a balance between talking about something really, really shitty, but also about something that means more to me than probably anyone in the audience, so I need to make sure I do it in a way that’s funny, and makes sense, and is true to people that I really, really love.

Devin Field

There’s some material I did that discusses race, and that was really hard to get exactly right, considering I’m a straight white guy up there talking about race. You want to get it right. So, that was material I took seriously in terms of trying to figure out how to make this fun for as many people as possible, and how to hit the right target. You’ll forgive me that I haven’t seen the specific cut, so I’m going off of what I did in the set. I close with a bit about going to the Anne Frank Museum in the Netherlands and a weird couple I saw there. That’s one that was a longer story about something weird I saw once, and that took a while to iron out to keep it interesting for the crowd the entire way. Stuff that’s just a story of an event that happened to you can often get boring for an audience, I think. You might think it’s fascinating, but they might not love the minutiae of it.

So I worked pretty hard on the pacing and timing of the lines in that story to make sure it was interesting, and not just like, “Hey, you want to hear about what happened on my vacation once?” I think that any of the material that touched on special issues or was adjacent to that stuff was something I worked pretty hard on to get right, because audience reactions can vary a lot when you’re playing with topics like that. I don’t think I’m an edgy comedian by any stretch, but you just want to do it right when you bring up a subject as big as that when you’re a straight white guy in a J. Crew shirt.

Emmy Blotnick

I’ve got a chunk in the middle there about the record producer, Max Martin, and it’s a little bit of a walk. Like, it’s a bit where if the audience doesn’t like it at the beginning, we’re in it for a little while. The bit is kind of like this weird freakout I had alone after learning how much influence he’s had over all the music I like. It’s a bit that I retired after the special, because not every audience has had the interest or attention span for that, and I’m glad the crowd in New Orleans did. It always feels safer to play around with shorter jokes than things like this, which require a bit of a “come with me on this journey.”

I actually wrote the bit originally for a show at UCB called Homeschooled. It’s like a PowerPoint-based show, and comics choose a topic they’re particularly interested in, and they flesh it out across slides and things. I had always been fascinated by him, because anybody who ends up being the mastermind of a universe like that and who has such a gigantic audience for what they do and makes such a widely consumed, inescapable thing is fascinating. So I sort of became obsessed with this dude who is, you know, in his 40s, and is basically deciding what music we all like. I just fell down a Google rabbit hole into the night. I mean, I feel like everybody does this from time to time, where all of a sudden it’s like 5 a.m. and you’re like, “How am I reading about subspecies of mountain beaver?” or whatever.

I learned too much, and I realized this guy was responsible for all the radio pop since I was a wee tot, and it just felt like it would be cool to unpack this, and how I discovered it at the same time. The PowerPoint … a lot of comics, I don’t think, like doing extra work, like where you have to do some homework to be able to participate in a show, and in this case, it was super useful, and having a PowerPoint when the bit wasn’t totally set — you could skip slides that don’t work, you could race through things, or hang out on slides that do work really well — it sort of came together from there. I found from running the bit around town that it didn’t need a PowerPoint or flowchart to work, which felt a little more pure, to be able to communicate the idea without having to go “… and if we’ll all just be patient for five minutes while the projection screen unrolls …” It got to a point where it was able to stand on its own.

Ryan O’Flanagan

I have this opening bit about Dave & Buster’s, and how I love Dave & Buster’s. It’s so hard for me to write a good opening joke, especially for a special, but really for any set, wherever I go. When I’m on the road, I usually try and talk a bit about the town and my experience so far. For the special though, you kind of want to open with something about yourself that lets the audience know who you are. I’m just kind of like a straight white guy, and I’m not super interesting, so it was hard to find a joke that would get the crowd on my side. I didn’t know if I was a little weird. I just tried to be relatable and disarming. I think it went fine. It was a crazy time though, because literally the night before the special, I went out to do karaoke at a nearby bar, and I lost my voice really bad. I don’t know if you can tell in the special, but I was just dying. I was told it sounded fine. I thought it sounded terrible. My voice cracked a bunch of times, and I had to go back and record a bunch of jokes over, because my voice kept cracking and giving out. The audience was super understanding and supportive though.

I was doing the bit separate from other jokes for so long. I mean, I talk about having just moved into my apartment, and having this crush on my neighbor, but really I moved in three years ago and wrote the joke then. The Dave & Buster’s bit is kind of new, and in the last few months I’ve been opening with that and then going into the bit about my deaf neighbor or the thousand dollars thing. In the moment, I realized, “Oh man, it would be funny if I kind of could bring back the Dave & Buster’s thing.” So, they were all just written at different times, and then you throw them into a set together, and you just gotta click in and realize it would be funny if you could bring this thing back.

The thing I like about it is it’s a little off, but I think the kind of persona I want to give is that I’m just a man, and an idiot. I’m kind of just a kid in a man’s body. So, right, everybody knows Dave & Buster’s, but also, it’s one of those things you never really think about, where you go, “Oh man, I haven’t really thought about Dave & Buster’s in like a year!” It’s never going to really blow the roof off the place, but it’s a silly, fun way for the audience to go, “Oh, he’s just a goofy idiot.”

Chris Garcia

By the time you get to be able to make one of these specials, you’re probably headlining and stuff, and you know what your closer is. I think the toughest part is putting the opener together, maybe. It’s your first crack at making people laugh and having them get to know you. Obviously, I end with a five-minute Magic Mike bit that’s very physical and crass, so I save that for the end, but, you know, I also didn’t want to be up there going, “Hey, I’m the Cuban guy!” So I was like, “I should be relatable and self-deprecating.”

So I thought, “Well, what’s a funny thing about me?” I didn’t really know, and so I was trying to figure that out for a while. Then, I was like, “Oh, I was a fat kid.” That is something that is very true to me still to this day. It still affects me, where I can’t help myself opening a box of cereal like a raccoon, because that little fat kid is still inside me. Aside from being left-handed, that might be one of the defining characteristics of me, this impulsivity to have to eat like that. I thought it would be like, “Okay, it’s very true to me. I think people will be able to relate. It’s kind of endearing. Let’s start with that.” A lot of those jokes were a lot newer than some of the other jokes. I was trying to fine-tune it for the special, but the intro is the toughest part. I was like, “Okay, I’m going to start with fat kid.” I feel like half of us were fat, so it made sense to start with that and take it from there.

Tim Dillon

I have a bit about ice cream, which is kind of funny. It’s a crowd-work bit where I ask the audience what brands of ice cream they like, and they yell those brands out, and I respond in a funny way. When you do a crowd work bit in a special, there’s always a certain amount of risk, because you don’t really know what’s going to happen. I think that I want to do it because it’s one of my favorite bits and something people kind of love. It’s just heightens the thing I do onstage. All of these things are integrated into this bit, but it is a bit that relies on the audience and what people in the audience are going to say. You have to take risks and have fun up there. I also think it’s a great representation of who I am as a comedian.

[The bit] originated with my grandmother. We’d always argue about ice cream, because I’d want her to buy Haagen-Dazs, and she’d always buy Breyers. I quickly realized Breyers was for the elderly. They quickly cornered that market with, like, Breyers’ peach. So, we’d argue about it, and she’d say to me, “You have no money. Just eat the ice cream I buy.” So it started there, and then it became really funny, this idea of ice cream as class. The idea of, like, the type of ice cream you eat explaining what type of person you were, and that idea I just started doing it onstage. It became funny, because you start to realize people have really strong opinions about ice cream. I’ve had people walk out of the show. I insulted Breyers, and a woman looked at her boyfriend and said, “That’s enough.” It’s really funny to me … that is the essence of comedy right there, what people care deeply care about, and what could be funny about that? So my getting up there and talking about ice cream kind of gets a rise out of people.

Sarah Tiana

The club bit took a long time. But the club bit itself, it started off with me just saying that I knew I wanted to talk about how all I wanted to do at a club was sit down, but that cost $1,000. That joke just started off as that, and I just started adding to the beginning and end of it. I worked that out mostly onstage. I wrote down a list of things I wanted to discuss, like the bouncer. I thought calling the bouncer “the guy on the stool” was funnier to me, the stool guy. We taped the special in December of last year, and I’ve actually added a few more things to that joke. I’m kind of bummed about not doing it as much. I mean, I still will, but every time you do a joke, it’s different. So, that joke took the longest to build because it is so long.

It takes hours and hours onstage and changing the order of the jokes and verbiage around until it clicks. You know, that’s why so many people think they can do comedy — they think it looks easy. That’s my job. My job is to make it look effortless and easy, but everything is thought out and placed. I’ll also add, just as a human being and performer, I have to put myself back in that moment so I feel like I’m in the club when telling that bit. I think it comes from the fact that I never wanted to do stand-up. I didn’t really know what it was. Even when I first started doing it, I had studied theater in Paris, and so being onstage in that moment was second nature to me, so when I’m performing and doing a bit, it takes a while to hone it down, because I’m re-performing it in different ways.

For the taping, the hardest part of doing that bit was the fact that I was wearing high heels. Normally, I’m not dressed up, so the line I had to change the most was about, I think I said, “I was wearing sweatpants.” Normally, I just say, “I was dressed like this,” and point to what I’m wearing. That usually is plenty. For the taping, I was like, “Man, I’m dressed up, and I can’t do that bit.” Honestly, that tiny switch weighed on me so much where I thought, “I don’t know if I can do this.” I was worried it was going to feel different. I wanted to get dressed up because it was a big deal, but the only thing it didn’t work for was the club bit. It was a real torturous part in my mind, and I had to practice that bit in the weeks before wearing high heels and dressed differently so it wasn’t as awkward.

Mike Lawrence

I would say the toughest was the political stuff. It’s tough in a lot of ways because we taped in December of 2017, and now it’s airing almost a year later, and we didn’t know when it was going to air. So you got to figure out a way to keep it somewhat fresh, and with this current regime, you don’t know what’s going to change and how crazy things are going to get, so all of the unpredictability of that is insane. Also, you want to try and go after both sides while also having a strong opinion. I have Hillary bits, but I definitely wanted to add Trump stuff too. I think it was important for me to say that I voted for Hillary. I think it’s important for comedians to take an actual stance — at least that’s my belief; obviously, anyone can do what they want. I think that was the hardest stuff. Everyone’s doing it too, so how do you say something different from what’s on Twitter?

I think the most important thing was touring it and seeing if it worked in different cities and different places, and making sure it wasn’t just pandering to one side was a big thing — the evergreen part of it you can’t control. I think Bill Burr is a great example of that. I remember a special where he was talking about Paula Deen, and it was a year after it happened. It was a great bit, but it was like … it already happened — we didn’t have his take on it, though. Time-wise, everyone is immediately commenting on things online, so you kind of have to hope that the quality makes up for the immediacy.

You definitely try and avoid having the same take, but you can’t be the first one to it a lot of the time. I think what most comedians choose to dwell on within a set is what makes their take unique. You watch Nanette, and she’s talking about all this art history stuff, and Picasso, she’s talking about stuff that happened years and years ago, but she’s making it relevant now and personal to herself — she’s making it relevant and important and vital. If something is important to a comedian, they can let the audience know that and hope that their bit is strong enough and that people understand. I always feel like you should trust the audience and assume the best of them.

Comedians on the Hardest Jokes to Write for Their Specials