Bestcasts asks podcasters to discuss the three most memorable episodes of their podcast. Ties are allowed/encouraged. For more podcast coverage, see Podmass, The A.V. Club’s weekly roundup of the best ’casts out there.

The podcaster: Paul F. Tompkins is a familiar name, face, and wardrobe in the realms of stand-up and TV comedy, with a number of specials (the latest, Laboring Under Delusions, was released in 2012) and credits (including Mr. Show, Best Week Ever With Paul F. Tompkins, and No, You Shut Up!) under his belt. But the recent podcast boom took the nattily dressed comedian to a new level of prominence, where he’s hosted ’casts like The Pod F. Tompkast and The Dead Authors Podcast and served on the casts of Superego and The Thrilling Adventure Hour. The stable of celebrity impressions and characters Tompkins developed on the Tompkast and Comedy Bang! Bang! have made him a frequent and sought-after guest in podcasting circles, leading to several episodes of Doug Loves Movies in which he’s served as one-man panels that include bizarro versions of Werner Herzog, Garry Marshall, Ice-T, and Buddy “Cake Boss” Valastro. With more Earwolf podcast appearances than any other guest—more than 100 episodes of Comedy Bang! Bang! alone—Tompkins launches his own Earwolf show, Spontaneanation, on Wednesday, April 1.

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The Dead Authors Podcast #43: Iceberg Slim: Ron Funches

Paul F. Tompkins: It was really hard to pick a favorite episode of this podcast. There have been ones where people are super prepared—those are great. The one that we did with Thomas Lennon in San Francisco for Sketchfest was amazing, because he had studied William Faulkner in college and he took it so seriously. Lennon Parham was somebody who didn’t know a ton about Flannery O’Connor, but that was a real favorite of mine as well. There was something about her performance where it felt like I was talking to a real person, like it stopped being a silly character type of thing. Jason Mantzoukas did not know anything about Plato and it was a blast.

I learned early on not to take it too seriously. It’s a comedy show, it’s not a college course. It’s supposed to be silly. We’re not trying to create an experience for the audience like, “What if this person were here?”

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Ron’s episode is the podcast at its best. When the improviser knows a good amount about the subject—doesn’t know everything—and gets around the fact that they don’t know everything by just rolling with whatever I throw out. The questions that I ask are not dependent on the guest knowing anything about the author at all. They can respond emotionally, because I’ll never ask, “How old were you when you did this? When did you put this book out?” They don’t have to look back, they are free to just say whatever they want to say.

A lot of these authors that we talk about are unpleasant people. There was a famous incident on our podcast where Ben Schwartz was playing Roald Dahl—who was a childhood hero of his—and he found out, as he’s playing this guy, that he was an anti-Semite. [Laughs.] He was crushed, but had to keep going and still play this guy that he just found out had, in a way, betrayed him. Ron was able to address and handle and embody the unpleasant things about Iceberg Slim, who was a pimp who beat women before he became a writer. Ron was able to not shy away from that and make it funny in a way that wasn’t all about, “Isn’t it hilarious to beat women?” He handled it as well as anybody ever could have handled it. It was always funny, but it never delighted in the unpleasantness.

The A.V. Club: Was that aspect of Iceberg Slim’s persona something you were worried before the episode?

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PFT: Oh, absolutely. Because it’s not funny. [Laughs.] This guy who is making money off of sex workers and beating them—it’s not hilarious. But it doesn’t mean that you can’t find humor around there. If you embrace the idea that this was an unpleasant person, there’s an opportunity for you to provide commentary on that. And that’s another thing that I think Ron skillfully did.

AVC: Was the discrepancy between the Slim’s vileness and Ron’s friendliness part of what made the episode fun?

PFT: Absolutely. I always let the guests pick the authors, and Ron narrowed it down to a couple. For him it came down to Iceberg Slim and Langston Hughes, and I said, “Whichever one you want to do.” I was so excited that that’s what he chose. Because the idea of Ron Funches—the sweetest soul in the world—playing this character was going to be hilarious.

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And Ron also blew me away on this because, like myself, he does not have any formal improv training, but he never faltered for a moment. He rolled with absolutely everything, and everything that came out of his mouth sounded like it was planned. He responded as if he was this person or this version of this person. You never caught him hemming and hawing on anything. He’s really pretty special.

AVC: There are some spectacular callbacks in this episode—specifically involving a UNIVAC. Do those come from being present in the moment?

PFT: It is about being present. And for me, the more relaxed the guest is, the more present I can be. Some people are really nervous about doing this show. They feel as if they have to honor the author—because this was an actual person who lived—or they feel like they don’t know enough about it and they’re going to get caught looking foolish or something. Ron was totally relaxed, was there to have a good time, so we were absolutely on the same page for that whole hour, and it just makes it easy. Those callbacks will come faster when I feel like I don’t have to be there to reassure the guests or make it easier for them or phrase questions in a certain way so that they will know they don’t have to have any fear about it.

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It was a perfect blending of attitudes. There’s pictures of us from that episode where we’re both laughing at the same time. Ron is famous for being a big giggler, and I’m no slouch in that department myself, [Laughs.] so that was also the most that both host and guest laughed through an episode. The role-play exchange of Iceberg Slim and the customer about the computer with the dress on it is absolutely one of the most satisfying exchanges I’ve ever had in any kind of improvisation.

AVC: Do you feel like your first job as a host is to make the guests comfortable?

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PFT: Yeah, absolutely. The title is host—there’s a reason. It’s not just, “Hey, the show is all about me.” [Laughs.] It’s your job to make the guests look as good as possible because that makes the show as good as possible. So much of it is about making sure they feel like they’re having a good time. It’s like a little party. They really have to feel like it’s fun because it’s supposed to be fun. It’s not supposed to be work for the guest. It’s supposed to be, “Please come onto this thing, I want to make you shine, I think you’re an interesting, fun, funny, smart person, and I want everyone to see that.”

Comedy Bang! Bang! #265: LIVE From RIOT LA: Paul F. Tompkins, Lauren Lapkus, Harris Wittels

AVC: This episode marks your debut as J.W. Stillwater, “the vigilante hero of Cumberbatch County, Florida.” He arose from a desire to create a character completely from scratch, right?

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PFT: Yes: that was not based on an actual person, that was something that I would be making out of whole cloth and I could control in a way that I can’t control other characters that are based on actual people. I was completely inventing the history: where he came from, where he was going, what he says, how he thinks. All of that was up to me. Because I so admire other character comedians—Andy Daly, James Adomian, Lauren Lapkus—who make up these people out of nothing. I saw how open it was. That really appealed to me—that it could be anything. You could do anything you wanted with it.

AVC: Though it’s not like your celebrity impressions are beholden to these people’s biographies.

PFT: They’re not, but there’s still a basis in some fact. That was my intent with doing those impressions: To make them characters in their own right. But it wasn’t so much about what their actual lives were. That stuff is there if I want to reference it, if I want to use it for fodder, but the idea was to attach these weird eccentricities or aspirations to these real people so I could make them my own.

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Eventually I realized, “Well, why don’t I just make up my own guy?” Then there’s a layer that I don’t even have to think about. Part of the idea with those characters was here’s this person that exists in real life—what if they felt this way about this thing? What if they wanted to accomplish this goal, and what if they had a secret addiction to cake decorations? That was fun for a while, but the challenge of having to come up with a new thing for these people over and over again got to be a little frustrating. And I just wanted to expand my own universe.

AVC: You picked a high-stakes scenario in which to expand that universe: a live episode of Comedy Bang! Bang! Were you nervous about presenting a new invention to a room full of people who were presumably familiar with your stable of Comedy Bang! Bang! impressions?

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PFT: At first I was really nervous about it, because I thought, “If people know that I’m going to be on the show, they’re going to be expecting a familiar thing.” For an audience, it is satisfying to see something live that you have heard previously. The idea of, “Oh, now I’m going to see this in three dimensions. That’s exciting.” But at a certain point it was easy to talk myself into it. “Wait a minute, you’ve been doing this for a long time. You have to take chances, and you have to trust that the audience will come along with you. I had to admit, “Hey, you know what you’re doing. There’s no way it’s going to be a complete disaster. The people might be unsure about it at first, but hey, you’re funny. You’re good in the moment, people will come along.”

That’s pretty much how it played out. People were very unsure about it at first. I think the laughs really build as it goes along. And in subsequent appearances as that character, people really like it. There’s a lot of stuff on Twitter that people were sending to me. I eventually [Laughs.] created a Twitter account for that character. It’s been a lot of fun to open something up like that.

I’m really glad I did it in that way, too, because it was a surprise. It was something that the audience was not expecting from me at all. Sometimes I’ll see people saying online, “I wonder if he’s going to do this one or this one.” And I felt like, “I’ve got to do something different. I’ve got to shake it up for myself and for the audience, and trust that that’s going to be a good move.” And I feel like it was.

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AVC: Do you feel like you surprised the other people on that episode—host Scott Aukerman and guest Lauren Lapkus—as well?

PFT: A little bit. Lauren and I had not performed so much together at that point. I don’t know if she had any expectation at all. Scott, I told him beforehand that I was going to do it, and he was completely onboard. And it’s his show. He never for a moment suggested, “You should do somebody that people already know.” Scott’s really supportive in stuff like this, and is always willing to shake things up. He likes taking chances. That level of trust goes a long way. If it’s his show and if he says, “Go for it,” then I’m going to go for it.

AVC: And you all really went for it at the end of the episode, introducing the Closing Sentiment-Off, which you and Lauren revived via Twitter on New Year’s Day 2015. Do you think that’ll become an annual tradition?

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PFT: I would love to do that. Lauren and I talked about that a little bit. I think if we can make it happen, that’s great. I don’t know if we’re willing to schedule [Laughs.] our vacations around it. But you never know.

AVC: Was there anything about the character Lauren plays in this episode, CB!B! intern Traci Reardon, that gave a boost to J.W. Stillwater’s debut?

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PFT: They’re characters that don’t complement each other in any way. They have nothing to do with each other and come from completely different worlds. The idea of, “What do they make of each other?” added to the fun. I think that was a good marriage of sensibility.

And that began my love affair of performing with Lauren. I love when people are mischievous—people like Lauren who get a look in their eye, and the fact that she is clearly surprising herself when she says things. She’ll say something and then she’ll try to stifle a laugh and I completely understand that. She responds, and then she’s processing it at the same time as everybody else. She’s become, so quickly, one of my favorite people to play with.

And that episode is obviously also special because of Harris Wittels appearance, even though we didn’t get to interact in the episode. He was always so much fun, and at least I got to hang out with him backstage before that episode. I was always so happy to see Harris. He always delighted me. He brought that out in people. I would just get a big smile on my face if I walked into a room and saw him there. It was always easy with Harris. You could joke around and have a real conversation. I will really miss those times.

The Pod F. Tompkast #1: Andrew Lloyd Webber, Ice-T, Tim Meadows, Jen Kirkman

AVC: How long did it take to put this first episode together?

PFT: It took a while. In a way we worked on it nonstop. We didn’t know what we were doing. We had all this stuff, all these different elements, and we hadn’t really worked out a regular schedule. We knew it was going to be an ongoing thing, and we knew there was going to be a lot of production involved, but what we should have done was recorded a bunch of them first, and then put them out. To this day, I don’t know why we didn’t do that. Everything would’ve been different if we had done that.

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It took days to get everything together. I had to write up the “Great Undiscovered Project” sketch. We had to record that—both sides of that conversation. Layer on the sound effects and all the production. The “nighttime on the Internet” sound bed was not an existing sound effect, that was something that we made ourselves. We collaborated on what the noises would be—that was a lot of trial and error, and finally Eban Schletter assembled it all. We had to book Daamen Krall to come into the studio to do the announcements. I had to write up the Theme Time Radio Hour intro—that cold open thing—and get my wife Janie to record that in the studio. I had to record the phone call with Jen Kirkman. I had to edit that down. I listened back to that episode for the first time in years, and I can’t believe how long that phone call was. And that’s the edited version. Now I would edit it even further. But it was all new.

The recording from the Paul F. Tompkins Show—that’s a really long bit. To me that was a real lesson in creativity versus assumption. What podcasting is, and what it can be, versus what people think it should be. The model of radio, of television, of anything is cut things down, cut things down, cut things down. As much as editing makes sense—you can only inflict so much on the audience—I always bristle at the idea that there’s a set length for things, and that the audience will only tolerate so much.

In that episode there are two great examples: Google Voice Theater is really funny. When I listen back to it, I’m like, “Wow, there’s so many ones that I read before Tim Meadows even comes out and does the ‘I Have A Dream’ speech.” But you cannot deny: People are laughing the whole time. I cannot say it should be shorter because people are enjoying it all the way through. I enjoyed it all the way through. There’s a push and pull with an artist where you have to say, “Okay, as much as I am enjoying this, I have to be aware of when it is indulgent.” When it is, “Okay, I like this a lot, but an audience might not like it that much.” Being in front of a live audience and having them respond to it right in front of your face, it’s very hard to make the argument that, “Oh, people aren’t going to like this for this long.” Because they did! The proof is right there!

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Then it gets into a thing of, “But: Will the audience after the fact enjoy it as much as the audience did there?” And then you get into other factors: If it’s just existing in a vacuum, maybe not, and maybe they’re not going to like it as much. But if they’re hearing the laughter—which is a real, live laugh track of actual people laughing, is that going to carry it through? And even thought that’s a really long bit, I stand by the unedited version of it.

That first call with Jen—absolutely I should’ve trimmed down. It’s very relaxed and the energy is a totally different thing. I was surprised at my energy on that call. It’s the quietest thing on the whole episode. I do feel that it accomplishes its task, which is to establish my friendship with Jen and how we interact with each other. That said, it should be way shorter.

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AVC: And that was only for the first episode. You wound up making 23 more of these.

PFT: Because we were building the template for what would be an episode of the Pod F. Tompkast, we pulled an all-nighter, which Eban is very accustomed to when he’s doing scores and stuff like that. I had not pulled an all-nighter in decades. I even crashed out on the couch in his studio for an hour. But I left that studio at dawn, and then we put it out. It never got to that point again, but it did not get easier to do that show, especially in the second season when we started adding in-studio guests and Daamen and I would interact with each other. It got more complex as it went on.

That was a hard show to do, but when I listen back to that episode, it all makes sense to me. I forgot that I laid it out in the introduction: This is all the things that I like to do. There’s going to be sketch, there’s going to be improv, there’s going to be stuff from the variety show, there’s going to be this phone call with Jen. Mission accomplished, in terms of what my mission statement was.

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There are some people that like the whole thing. There’s a lot of people that like this element, but they don’t like that element. There’s people who fast-forward through those rambling monologues—which to me, that really is the soul of the show. Me stream-of-consciousness talking while Eban plays the piano and you hear that hum and the beeps and boops in the background—that is the show to me.

AVC: When listening back to those monologues, were you ever surprised by what you said?

PFT: I would be surprised by the things that I said, and I would be surprised by the things that Eban was playing in the background, because I wasn’t always aware of them while they were happening. He really does amazing stuff on that show. He’s listening, he’s inspired by the things that I’m saying. He picks up on so much stuff and takes it to another place that I would have not expected. Eban Schletter is pretty amazing, and I’ll never stop saying it.

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AVC: Could you conceive of doing your new podcast, Spontanenation, without Eban?

PFT: No. It was the same thing with The Pod F. Tompkast. It was a long process of figuring out what to do. It’s also why there are so many different elements to that show. Who says I can’t do everything? I want it to be different than the usual, “sitting around, talking” podcast—which I enjoy listening to and I enjoy guesting on, but I don’t want to just jump into that very crowded pool. I want to do something that’s different.

And then with Spontaneanation it was like [Laughs.] I know I don’t want to do a super produced and involved thing again, so what show can I do that’s totally in-the-moment, that requires no preparation? And I had to go back to, “What are the things that I like to do?” I love doing those monologues. I love talking over Eban’s piano. There’s something about that that’s very enjoyable to me. It’s satisfying and it’s calming and it’s soothing—him playing opens up my brain.

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And I thought, “I do enjoy talking to people.” From the Tompkast, I enjoyed those free-form conversations where there were no notes, no bullet points, no pre-interview of, “Bring a funny story to tell.” Stuff like that episode with Gillian Jacobs in the second season, when she tells me about her grandfather, who was this little guy who had to lie to get himself in the army, because he wanted to fight in World War II, and he had these very brittle bones so he had to be [Laughs.] really careful. That is amazing to me, and I don’t think that would’ve come out if I had some pre-interview where I said, “What do you want to talk about?”

The way we’re doing it with Spontaneantion is I get a question to kick things off that comes from the previous guest. The person submitting the question doesn’t know who’s going to be answering it, and the person answering the question doesn’t know who is submitting it. The questions so far really run that gamut. Some of them are really deep questions, and some of them are just absurd questions. It’s been such a fun way to start that conversation. It straddles the line between an earnest interview—because I can’t help but to want to know more about the people that I’m talking to—and an opportunity to make jokes.

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And then that will inform the improv. And that, to me, is the newest thing: It’s a narrative improv. So as opposed to Improv For Humans or something like that—it’s not short scenes, it’s one story that’s told over the course of a couple segments. That’s the thing that’s most exciting, because it’s the biggest challenge for me. I’m getting people that are very seasoned improvisers, and I’m the new guy, and I am throwing myself into this thing, and it’s a crash course in improv for me. It’s drawing on all of this stuff that I’ve learned from doing improv on podcasts: From working with Superego, from working with the people that I work with on The Thrilling Adventure Hour. I’m finally getting to do this, putting all of that knowledge to work, and learning new things every time.

AVC: In your Reddit AMA, you said that the Tompkast will, “never truly be over.” Can you see yourself ever assembling another episode of that show?

PFT: In a perfect world, I would love to do like a “special” every year to keep that idea alive. It requires so much time, so that sounds about right to me: Once a year. I don’t think that’s crazy to think that we could do that.

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It’s funny to me how people don’t [Laughs.] seem to get that it’s very involved. When I listened to the first episode, I was like, “It was crazy to think we could do this every month.” And when I think about what we were doing at that time: Eban and I were doing that podcast and we were doing the live variety show at Largo—which was another thing I had to stop doing because it was just too much work to do every month. And we were both doing the things that actually paid us to live. So it’s insane to me how involved it is, and that we were able to do it for two years.

But still, people are like, “Why aren’t you doing it?” To me the answer is in the episodes. You can hear [Laughs.] exactly why we aren’t doing it. People are the same with poor Matt Gourley about Superego. “What’s the hold up?” And it’s like, “Well, listen to the show!” [Laughs.] Really listen to the show, and listen to other podcasts—and do you see what the difference is?

AVC: Hopefully Spontaneanation turns out to be the less-arduous task you’re hoping it is.

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PFT: So far so good. It’s been a treat to do it at Earwolf—they’re hugely supportive. And I’ve gotten a lot of really good people on the show, and it’s been a lot of fun. It’s great to be working with Eban on a regular basis again.

I really hope that the shock of the new will not prevent people from enjoying it. I would remind people: It’s a new thing. Give it a chance, and give us the chance to find our way with it, because chances are it will evolve as time goes on, and it’ll get better and smoother and sillier.