Paul F. Tompkins is a funny, funny man. This isn’t an opinion; Rather, it’s a statement of fact. Whether he’s delighting audiences with his uniquely off-beat stand-up stylings, hosting political debates with a panel of puppets on No, You Shut Up, appearing on every podcast under the sun (especially Thrilling Adventure Hour and his own), or hosting his alternately hilarious and heartfelt interview show Speakeasy, you can bet your bottom dollar that not only will he entertain the pants right off of you, but he’ll also be better dressed than you, to boot. Now, his MadeMan.com series Speakeasy is entering its third season, and I was fortunate enough to catch up with the comic to pick his brain about everything from how the show has evolved over time, the tenuous fate of the critically acclaimed Pod F. Tompkast, what the “H” in H. Jon Benjamin stands for, and other pressing, burning questions. So, sit down, pour yourself a drink and prepare for the unfettered wisdom of Paul F. Tompkins.

Nerdist: Let’s talk about Speakeasy, which is coming back for its third season–very exciting! How’s the response been to the show so far, and how has it evolved since it first started?

Paul F. Tompkins: The response has been terrific. The people that enjoy it really enjoy it a lot. People have said amazingly nice things to me, and complimented my skills as an interviewer, and they loved the guests, and they loved the format of it. And a lot of people remarked about how beautifully it’s shot. I want to reiterate, our director of photography, Martim [Vian], is an amazing talent. It’s just a terrific crew that throws that all together, in a place that’s an actual functioning business, and makes it look like it was a beautiful set built just for us — all these different places we go to.

The way it’s evolved, it started out, we would do these shorter interviews. We would record for about an hour with each person, and then it would be chopped down to about 5 to 8 minutes, and then we expanded it, which I really loved, to make it an average of about a 20 minute episode. I really enjoyed the format of it, of being able to have an in-depth conversation with people, and having it not be all about just the typical talk show anecdotes that are all ready to go. I was lucky in that way, because we don’t have an audience. When you have an audience, the feeling of having to entertain on the spot is much more powerful, so it tends to err on the side of caution, and have stories that are ready to go with their guests. But without them we have a more intimate feel, and so we can have a more intimate conversation.

N: So you get to cut through some of the more superficial, surface-level stuff, and get to the real nitty-gritty of it.

PFT: Yeah, well, you know what it is? You can have a conversation that you don’t have to worry where it can lead. You can follow tangents, and you can come up with questions in the spur of the moment, than if you’re having to worry about an audience of people watching it, where it feels like a live setting. It just becomes a quieter place, it’s a darker place, and you’re at a bar, so for me and the guests, it just naturally becomes a more conversational kind of thing. You feel less like you’re performing and more like you’re talking.

N: What’s been your favorite or most enlightening moment or guest on the show so far?

PFT: Oh, man! I have to say that we’ve been lucky in that we’ve had so many interesting, thoughtful people on the show, who are famed for rolling with what’s happening. I loved talking with — I love talking with people who have a family, because it’s really interesting how people are able to make a normal family life work in a very chaotic business.

It’s hard, sometimes, but in a business where sometimes you don’t know if you’re going to be able to see your kids in person for a month at a time — that is always fascinating to me. People who come from the theater also fascinate me. I loved talking with Kaitlin Olson from It’s Always Sunny in Philadelphia; Michael Rooker from The Walking Dead, who was a fascinating guy; Dominic Monaghan from The Lord of the Rings. And then there’s a lot of people that I know personally that it’s been great to open up with. One of my favorite recently was Key & Peele. We talked for such a long time about comedy, and I love talking about that stuff. I could have talked to them about that forever.

N: Yeah, that’s really cool. Especially when you know someone, or you happen to be in the same business, you can sort of just get into the stuff that an outsider might not be able to ask the same questions, because they don’t have that inside knowledge.

PFT: Yeah, exactly.

N: So when we last spoke, I think it was back when the show was first debuting, I asked you who your dream guest would be, and your nightmare guest. You said Steven Colbert, and Joseph Kony, respectively. Is that still the case?

PFT: [laughter] You know what? I stand by those!

N: Good! [laughter]

PFT: [laughter] I forgot all about that. Although you know what? Kony would be a good get, I’d have to say. Dream guest – Stephen Colbert. Nightmare guest – Freddy Krueger.

N: That would be a real nightmare, although I’d have to wonder what his drink of choice would be.

PFT: Well, probably, like, blood.

N: Depends on what type it is.

PFT:  Yeah, especially if we filmed at a bar on Elm Street, the odds would be against me.

N: Exactly. You’ve got to choose your set wisely that day. In a bit of cross-pollination, have you ever considered bringing a Dead Author onto Speakeasy to see what happens?

PFT: Oh, I would love to do something like that! I love it when worlds collide, and so I would — that would be wild. Although — yeah, I think I could pave the way, either me as myself interviewing a dead author, or H.G. Wells interviewing a live author, would be a lot of fun.

N: Yeah, maybe just like an episode that is “Lost in Time” or unearthed from the archives.

PFT:  [laughter] That would be crazy!

N: So the show is on Mademan.com, and you’re a very dapper fellow yourself. I felt validated in my wardrobe choices recently when I saw you rocking a velvet blazer on @midnight. What is one piece of sartorial advice you would impart to your fellow men out there?

PFT: Dress how you like to dress. Don’t worry so much about rules. I love clothing, and I love fashion, but I think that there is too much pedantry in fashion, and saying, “You have to wear all of these things together; you can’t button this button.” You know, all of that kind of stuff. I think of that stuff as a guideline. If you’re uncomfortable dressing up — if you’re getting married, let’s say, and you’re not a dress-up guy, but you want to look nice for your wedding, and you’re looking for advice to do it right, there’s plenty of places out there to find the general rules of men’s fashion, so you can feel like you’re not worried about it.

But if you just let clothes — I used to hear that stuff so much more, and now I’ve found I don’t care. Like, wear what you like, you know? And wear it the way you want to wear it. If you feel good about it, that’s all that matters, because we live in an age where there are so many different types of fashion and modes of dress. It’s not like the ’50s, where men wore suits, the end. You can wear whatever you want in a variety of situations and locations, so I would say just be confident in what you’re wearing, and enjoy it!

N: I think that is very sound advice. I think a lot of people get intimidated, because as you mentioned, the pedantry inherent to the industry. The rules are guidelines, as opposed to strict finalities.

PFT: They should be. I had a guy — I did a show in London, and it was summertime. I was wearing a seersucker suit, and I was wearing a red polka-dotted bow time, and I had a pocket square that was navy with a light-blue border, and this guy came up to me after the show, and he said “I was appalled at your tie and pocket combination. You can’t wear a black pocket square with a red tie.” I said, “It’s navy.” He said, “No, no! Always complementary, never matching.” And he handed me a bag, and he had gone out right after the show to a store nearby and bought me a pocket square — that’s how much it offended him. I had tapped into his weird fashion OCD, that he couldn’t bear the idea that I was doing this.

N: Oh, my goodness!

PFT: And he was so adamant about it, that that’s when I realized, you know what? I don’t care about this stuff anymore, and if people ask me “Should I button this button?” my answer is going to be, “Do whatever you want!” That made me realize how ludicrous it all was. What we’re talking about is just ridiculous. It’s 2014. Button whatever fucking button you want to button.

N:  Yeah, well, on the opposite end of the spectrum, if you do have people like that, that’s how you get free pocket squares.

PFT: Well, that’s true. I do still have that pocket square. I have yet to wear it!

N: [laughter] You don’t want to seem continental to that touchy London crowd. I understand. So I also solicited some questions from Twitter and from our audience, and there are some pretty delightful ones in here. I also spoke with H. Jon Benjamin this morning, so they wanted me to ask you, “What does the H. in H. Jon Benjamin stand for?”

PFT: Oh — Hompkins.

N: [laughter] Of course, of course it does.

PFT: The H that people try to put in my name–that’s where it belongs.

N: Interesting.  You know, you’ve got to have it somewhere.

PFT: Exactly.

N: Another Twitter question: If you had to eat one French fry per minute for the rest of your life, how long do you think you’d survive?

PFT: One French fry per minute, for the rest of my life.

N: Yeah, like a potato-filled version of Speed.

PFT: Do I get to sleep?

N: I presume so, as long as you’re eating a French fry per minute.

PFT: If I get any while I’m asleep…

N: Yeah, they didn’t specify. I assume an IV drip of potato mush would work.

PFT: I’m going to say, if I get to sleep, without — that’s my only break from the French fry eating, I would last a week.

N: A week.

PFT: If I don’t get to sleep, I’m going to put it at 48 hours.

N: Wow. That’s a grim future in this potato-filled hell.

PFT: I do like French fries, though.

N: Yeah, I’m a big fan myself. Speaking of things I’m a big fan of, can we expect any more Pod F. Tompkast in our lifetime?

PFT:  Yes, this year. Eban Schletter and I will be going in the studio very soon. It’s a very busy time. This year started off with a lot of running around, but there’s a bunch of stuff written already, and we’re going to be getting back in the studio very, very soon.

N: Well, you’re always a delight on your myriad podcast appearances. Particularly, I’m a big fan of when you do celebrity impersonations, like Werner Herzog or Cake Boss. I’m curious — have you ever met any of your real-life counterparts, people you do impressions of?

PFT: The only people I’ve ever met are John C. Reilly and John Lithgow. And when I met John Lithgow, I hadn’t been doing the impression. That was definitely the inspiration for the impression was meeting him. John C. Reilly, of course, I’ve worked with a number of times. The only other one I came close to was Ice-T. He just launched a podcast, and within a week of his podcast launching, I got an e-mail from my agent saying Ice-T would like to have you as a guest on his podcast. And I said, “Oh, of course!” I was very excited and nervous about it, because I knew he was going to make me do the impression. I knew the reason I was being asked was because I had been doing an impression of him, and he had been apprised of that impression. I knew that he would make me do the impression for him.

So I get this call, a couple of days later, so they set it up, and I’m talking to Ice-T, and so we’re talking and I’m very excited, and he says “Do the impression.” I do it, and he says, “Aww, that was terrible!” which really made me laugh. Then I found out the next day, that that was not Ice-T, it was an Ice-T impersonator, this guy Rockwell — a comic in New York, who pranks people as Ice-T — like, he’ll call up the Howard Stern show, and he does a really great Ice-T impression. It’s way more accurate than mine. And so they ran it — it’s up now, they edited it down, it’s like 5 minutes, but we talked for about 25 minutes. So physically I wasn’t talking to the real Ice-T, but I do appreciate the crazy, meta aspect of it, of two guys who do Ice-T impressions talking to each other.

N: [laughter] That’s amazing.

PFT: Ice-T is a great sport about people doing impressions of him, apparently, obviously, and so I have no choice but to be a great sport about being pranked by Ice-T.

N: Exactly. It’s like the weird circle of life, and it all revolves around Ice-T.

PFT: [laughter] Yeah, the circle of life. Definitely what they meant in The Lion King by the circle of life!

N: I just have one last question for you, and it’s a bit of an oddball, so please bear with me, not that the french fry thing wasn’t. What would be inside your ideal burrito?

PFT: Oh, let’s see. I know this is important. We cannot let the Nerdist folks down. Umm… I’m going to say, put some chicken in there. Put some rice in there. Put some cheese in there. Put some sour cream in there. Put some Mike ‘n’ Ike’s in there. Put some Benadryl in there. Top it all off with sauteed onions, and I think we have the perfect burrito.

N: I think so too. You’ve got the textural element, you have the sedative element, you’ve got the protein. You’ve got everything.

PFT: Yeah, it’s really a well-balanced…

N: Yeah, you won’t even need to think about a food coma, because the Benadryl will just slowly ease you into it.

PFT: Exactly! So the burrito by itself would put you on the path to sleepiness. The Benadryl will make sure you arrive safely.

N: Yeah, it pushes you over the cliff.

PFT: Exactly. That’s how I get to sleep.

N: Do people sleep in other ways? This is the first I’m hearing of it.

PFT: If they do, God bless them.

N: Yeah, they’re braver than I. Well, Paul, thank you so much for taking the time to talk to me today. It’s always a pleasure speaking with you, and I’m really looking forward to your billion projects out there, Speakeasy included.

PFT: [chuckles] Thank you! I’m like Chris Hardwick, only I don’t get paid for anything.

N: [laughter] Oh, no! There are worse things to be. You’re like the intern version of Chris — doing it for college credit.

PFT:  Yeah, right! [chuckles] It was a pleasure talking to you again. Thank you so much!

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And while you’re here, check out the Chris Hardwick episode of Speakeasy!

You can watch brand new episodes Speakeasy – like this week’s featuring Eric Andre – on MadeMan.com, and follow Paul’s myriad projects on Twitter!