Paul F. Tompkins is, undeniably, a man’s man. With a Ron Swansonian mustache, a sartorial style that would make Don Draper jealous, and a boundless charisma, Paul F. Tompkins is exactly the kind of guy with whom you’d want to sit down and have drink. Fortunately for us, the folks over at Made Man agree and have given the comedian his own show called Speakeasy, in which Tompkins and “Hollywood’s most iconic men” sit down to have a conversation over a nice, refreshing cocktail.

[youtube http://www.youtube.com/watch?v=7bEYzQ4IyVU?rel=0]

In today’s debut episode, Modern Family‘s Ty Burrell pulls up a chair to Tompkins’ table, but you can expect everyone from Zach Galifanakis to Nathan Fillion and even our own Chris Hardwick to swing by the mahogany-laden lair for a tête-à-tête with Tompkins. All of this comes fresh off the heels of his most recent hour-long special on Comedy Central, Laboring Under Delusions. I had the chance to catch up with the mustachioed man himself to find out what’s in his glass, what’s on the horizon, and who is definitely banned from pulling up a chair at the bar.

[youtube http://www.youtube.com/watch?v=YdbRPIDCQLw?rel=0]

Nerdist: First and foremost, congratulations on Speakeasy. I just watched the trailer and it seems awesome, definitely right up your alley.

Paul F. Tompkins: Oh, yeah, I was really pleased. The trailer looks really nice and it’s such a fun and easy gig that kind of dropped into my lap. I’m really pleased with how it’s all unfolding

N: How did you get involved with the project?

PFT: One of the producers, Rebekka Johnson, is a friend of mine — she’s one of the Apple Sisters, the comedy trio — and I’ve worked with those guys a bunch of times. A show came up and she thought I would be a good host, so I came in to meet with them about it and it turned out to be a lot more fun than I thought it was going to be.

N: Speakeasy seems almost like a natural progression for you. What is it about the show and the format that excites you?

PFT: Well, it’s really casual. There’s no audience which makes everything much more relaxed for me and the guest. I like that it’s really just an interesting conversation with an interesting person.

N: We’ve got to know what was in your glass. What’s your poison?

PFT: Oh, I’m a whiskey man. If I drink spirits, I like Irish whiskey. I don’t really have a taste for scotch; that’s kind of intense stuff that you really have to develop a taste for. You know, let’s say I have a more of a plebian palate. I also like wine. I got into red wine not that long ago. I never really liked wine before; it’s only in the last handful of years that I’ve really come to enjoy it and I realized that anytime I had wine before it was wine at a comedy club. [laughs] Like bar wine, which is just disgusting. It’s nice to realize, oh yeah, if you actually go to grown-up places, you can actually find a decent wine.

N: Not a jug of Carlo Rossi?

PFT: Yeah, exactly. Value is what clubs are all about.

N: Are you one of those guys who can pick out the hint of sandalwood and all that other stuff from a glass of wine?

PFT: Not quite. Although I am surprised that my palate for wine has developed even slightly to where I can tell the difference between one wine and another wine, which did not used to be the case. [laughs]

N: As your comedy career has progressed, you seem to have transitioned rather seamlessly from more of a conventional stand-up to more of a storyteller. How has your approach to comedy changed over time?

PFT: Yeah, it has been sort of a gradual thing. It wasn’t a conscious decision; it just started happening. I started experimenting with telling stories from my life onstage a little bit at a time and I really liked the response, so I started doing it more and more. Then, I started thinking in those terms, seeing stuff as grist for stage material that I probably wouldn’t have before when I was more of a joke-oriented comedian. It’s been really rewarding and a really wonderful thing because there’s an intimacy established with the audience that I didn’t really quite have before. I can really feel it. When people are laughing at something that’s relatable in that way and it’s not just a “hey, did you ever notice?” situation, I find that I don’t have to ask the audience if they can relate to this. If I get to the emotional core of the story, especially like the last hour I did, which is all about various jobs I’ve held, and I’m talking about being on a movie set, that’s not necessarily going to be relatable to a large part of the population. When I get to the emotional turmoil — or whatever I was going through — everyone can relate to that and apply it to a situation in their own life. It feels really good.

N: When you’re doing an hour-long set like Laboring Under Delusions that has more of a thematic tie throughout, is the writing process different than it would be for a more conventional hour? What’s the process of creating that for you?

PFT: It’s the same in a lot of ways because the joke-writing approach for more conceptual stuff is asking, “How do I get the most out of this concept?” You know, really thinking about it and examining it and asking, “Where will it lead?” A lot of comedians certainly go through this — I did when I was younger — you’re so excited to get a laugh that you sort of set up the premise, you get one joke out, then you move on to the next thing, because you get nervous that if you wait too long, people aren’t going to laugh, they’re going to get mad at me; you feel that if you have a variety of things to talk about — I remember seeing Chris Rock’s first special Bring the Pain, the material that he did, he really examined all the different facets of a given topic. Sure, he had longer stuff that he trimmed down, got it down to the best stuff, but he was using every part of the buffalo, if you know what I mean. It’s a similar thing with these stories where 90% is done because it happened to me. There’s your premise. Then I have to fill in, get to the bottom of “what was I feeling when I went through this? What feels unusual or amusing to me?” or whatever, and then begin the translation process from my brain to a group of total strangers in order to have it all make sense.

N: Going through the overall arc of Laboring Under Delusions, do you think that the payoff would have been as sweet if you had been a wildly successful stand-up right out of the gate or do people need to go through that awful employment crucible so that they have something worth talking about?

PFT: Well, most comedians are comedians because they have had a bunch of unpleasant experiences that they’ve had to turn into something enjoyable in one way or another. [laughs] If I’d been successful when I was younger, that probably would have brought a whole host of issues and calamities because a lot of people are not equipped to deal with wild success at a young age. I certainly was not able to — what little success I had, I was not able to. Who knows? Some people have a great head on their shoulders and can weather these sorts of things. I was a person who thought I was wise beyond my years, and it’s only decades later that I finally realize I wasn’t at all.

N: You’re something of a staple amongst comedy podcasts, your work on our Thrilling Adventure Hour included. How important is a podcast for a working comedian or is it something more for fun that has the pleasant side effect of increasing your web presence? 

PFT: I think it’s a thing that has been great for me to keep creating and keep my mind limber and to be able to do a lot of different things. On my podcast, [The Pod F. Tompkast], I’ve done a lot of voices, sketches and conversational stuff — all of that has been really helpful for me for keeping in shape, as it were, for the audiences. The impact that it’s had on my ability to reach people, I cannot underestimate it. It’s been very real and very apparent and great. It’s definitely brought people to me and what I do, whether it’s on my podcast or Thrilling Adventure Hour or Comedy Bang Bang. It really does make a difference; it’s a bit of a joke that I appear on a lot of podcasts, but it’s an easy and fun thing to do that’s going to help me reach people, so I don’t see too much of a downside to it.

N: With what some might call a glut of podcasts out there, many of which feature the same people, do you think it ever could impact DVD and album sales in a negative way?

PFT: Ah, it might, but you know, I think it’s a very small segment of people that will say, “Why buy the cow, when you can get the milk for free?” You know? I think people that are comedy fans are going to say, yeah, here’s the stuff on the podcast that you can have any time, but the stuff being offered on CD or DVD is totally different. It’s worth paying for. I think a lot of people see it as sort of a quid pro quo kind of thing, like, “Hey, this guy has given me a lot of stuff for free, so the least I can do is buy this album one time.”

N: Along similar lines, given the recent trend of comedians like Louis C.K., Jim Gaffigan and Aziz Ansari adopting a digital self-release model for their most recent specials, is that something you would consider in the future?

PFT: I think it’s great. I wish I were able to do that. Chris Hardwick and I had a discussion with a guy about this at a recent Thrilling Adventure Hour who was saying, “Hey, how come you guys don’t do that?” and we had to explain to him that it costs money to produce the special. You know? You have to have that money first in order to shoot the thing to make it look good and professional and you hope that you’ll make your money back on that. With the Louis situation, I believe he didn’t self-produce that special; I think it was actually produced by somebody else and they weren’t going to do something with it, but he had the rights, he owned it, so he decided to release it on his website. I could be entirely wrong, but I remember hearing that. It might not have been the plan from the beginning, but it became the shrewd, smart thing to do. Until the ability to shoot a professional-grade comedy special all by yourself becomes an easy thing to do, I don’t think it’s going to be the model for everybody. People ask me why I don’t do it all the time. Comedy Central had hundreds of thousands of dollars to spend on a comedy special and I did not, so… [laughs] Also, I’ve been part of a record label, the last few releases I’ve put out have been on a very small label. We split the profits 50-50 and nobody was praising that, but we’ve been doing that for a while. The DVDs that I put out — it was not five dollars, but we put it out on a small label. Five dollars seems to be that magic number where people are like, “Yeah, okay, how bad could it be?” [laughs] To do something like that would be great, but not everyone can afford to charge five dollars.

N: Who are some of your favorite working comics today?

PFT: Oh, Jen Kirkman, she’s always my number one. She’s a dear friend of mine, and you know she writes on Chelsea Lately, is frequently on the roundtable and After Lately. She’s someone who I think has really come into her own as a standup and has been touring around a lot. I think she’s really a unique voice and I really like what she does. She really makes me laugh. Maria Bamford, I think, is absolutely amazing because what she does, on the face of it, this very silly stuff — character voices and everything — but there’s a real lyrical edge to what she does that has a lot of bite to it. I’m very much in awe of what she does. Kristen Schaal, who is, you know, on Flight of the Conchords, The Daily Show, I just think she’s brilliant. The absurd, silly stuff she does really tickles me to no end.

N: Any other projects that you have coming up about which you’re excited that you can share with us?

PFT: Kind of, I’m developing something for Comedy Central right now that will probably be shooting pretty soon. I don’t know if I can say too much about it or if I’m just worried about jinxing things. [laughs] But it’s in the early stages — the pilot — and I’m very excited about that.

N: Was this the pilot you and Tom Scharpling were working on?

PFT: No, no, the network passed on that, so now I’m doing this thing.

N: Who would be your dream guest to get on Speakeasy?

PFT: Oh, I think Stephen Colbert. I am a huge admirer of his, I think that show is the funniest show on television, hands down. Counting scripted sitcoms, it makes me laugh like no other, night after night, and I kind of marvel at it every time, like how is this still this funny? It’s so densely packed and layered and his performance is amazing. Everything happened the way it’s supposed to happen and it’s so rare to have every element firing on all cylinders. And I love the fact that he does so much charity stuff with his show. If you have a forum like that, why not do that? He puts his money where his mouth is in terms of being a decent moral person and that’s the other side of the satire sword, not just standing back. It’s fine to make fun of someone and that’s enjoyable, but to not only point out that the emperor has no clothes, but to say, “You know what else? There are other people who need clothes and I’m going to try to take care of them because people take care of each other,” is a really amazing thing.

N: On the other side of the coin, who would be your nightmare guest?

PFT: Probably Joseph Kony.

N: Well, good luck getting that guy on the show.

PFT: Oh, he’d better not show his face at Speakeasy.

N: Let it be known! Kony is not welcome on your set.

PFT: No softballs, Kony. I’m going to ask you the hard stuff.

N: Well, at least make sure he has a drink.

PFT: [laughs] Exactly.

Speakeasy, hosted by Paul F. Tompkins premieres today on Made Man with new episodes every Monday. His most recent special, Laboring Under Delusions, is available now. You can keep up with Paul on Twitter and let him know what kind of cocktail to serve Kony if and when he does the show.