Paul F. Tompkins is nothing if not prolific. After moving to Los Angeles from his native Philadelphia, the comedian’s career began when he landed a role as staff writer on the influential HBO program Mr. Show with Bob and David. Since then he has toured as a stand-up, released acclaimed specials (most recently 2012’s Laboring Under Delusions), performed voiceover work in programs like Bob’s Burgers and Netflix’s BoJack Horseman, and become a major figure in the comedy podcast world (he is a regular on the old-time radio themed podcast The Thrilling Adventure Hour and has appeared several times on Comedy Bang! Bang! in the guise of filmmaker Werner Herzog).
One of Tompkins’ latest gigs is Speakeasy, a web-based interview show where the comedian talks with notable actors and writers over drinks. The list of guests so far includes Nathan Fillion, Weird Al, David Cross, Sons of Anarchy writer Kurt Sutter and, most recently, Bob Saget.
We recently caught up with Tompkins to discuss the show as well as his love for fashion, the future of his much-adored podcast/variety show The Pod F. Tompkast and the roughest Speakeasy interview he ever had.
It seems like you always involved in something, whether it’s touring, your Largo shows, podcasts, voiceover work. Are you the type of person that feels as though they always have to keep busy?
Paul F. Tompkins: My career is made up of a lot of different things. It feels like a necessity. It’s not like I am a workaholic in that way, like ‘I have to be working all the time!’ I’d like to have some time off [laughs]. In order to feel like everything is taken care of, I feel like I always have to say ‘yes’ to things. Unfortunately, it’s a lot of things that pay a little amount of money as opposed to one thing that pays a big amount of money.
When you were first coming up in the entertainment business, did you have any specific goals about where you wanted to be—whether it be as a writer or as a performer—or did you just go in with an open mind?
Tompkins: I always wanted to be a performer. When I first started doing stand-up back in Philadelphia, the idea of being a professional writer was completely beyond me. It didn’t even occur to me that that was something you could do. I had started in Philly and was just trying to figure that out. It was beyond my comprehension that you’d move somewhere, have a different career and things like that. But yeah, I always wanted to be a performer and when I did start to write for TV on Mr. Show with Bob and David back in the ‘90s, that’s when I realized I wanted to keep performing. I’m not one of those comedians that enjoys the writing side over the performing side. You’ll see that a lot in writers’ rooms on sitcoms and late night shows. They’re staffed with a lot of people who come from stand-up and those are, by and large, people who enjoy the joke-writing process more than they enjoy the performing process. Which I get. Some people like that puzzle. They like solving the puzzle of the blank page. For me, writing is just a means to an end. It gives me something to do on stage [laughs].
Paste: Was Mr. Show your first major gig?
Tompkins: Oh yeah, absolutely.
Since then, it’s become such an influential program. Were you aware at the time that this was something radically different or did you just not have a frame of reference for it?
Tompkins: Oh no. We all knew this was something special. I’d seen Bob and David do the live shows that led up to Mr. Show. It was absolutely exciting. It felt new and fresh and different. There were certainly influences you could see, but they built on their influences as opposed to just aping them. It was a really exciting time. That was another moment when I realized writing wasn’t for me. I thought, ‘This is the best it’s ever going to get.’ I was writing for these people that I could not respect or idolize more and I thought, ‘If I’m still not completely satisfied I should get out of people’s way.’
When do you feel like you really came into your own as a performer?
Tompkins: I think within the last five years. I really do feel like it’s an ongoing journey and continues to be an education for me. I really feel like I’ve started to fully understand the work I do and how to do it better and challenge myself in the best possible ways. But that’s a part that’s only come to me fairly recently.
Can you tell me a little about Speakeasy? Was that an idea that you had or someone approached you with it?
Tompkins: I was approached by the producers, one being my friend Rebekka Johnson who directs the episodes. She says, ‘Hey we’re doing an interview show and you chat with people over drinks at a bar, is that something you’d be interested in?’ It sounded great. It’s the kind of thing I like to watch and would love to participate in. That was pretty much it. I jumped on board and it’s been one of the great joys of my career some of those interviews. It’s really been amazing. I’ve gotten to talk to some really cool, interesting people.
I like to joke that, in the comedy world, you’re a Kevin Bacon figure in that a person could connect any comedian to you in six moves or less. I know a lot of your guests you’ve worked with in some capacity—
Tompkins: I’m always surprise by that! Which sounds stupid, but I’ve done 70-plus of these episodes now and we’ve got a few coming out, but it’s shocking that my path has crossed with the majority of them over the years. But it’s a small world and, especially in this business, it’s an even smaller one.
What would you say is the ratio of people you know well to the ones you maybe don’t know as well?
Tompkins: The people I know well—that’s been a very small handful. That’s really just been, out of 71, maybe five or six. Then there’s a larger group of people I’ve worked with once or twice at least. Then, on the other end, there’s some people I’m meeting for the first time.
Do you prepare question or do you prefer to make it kind of a conversation?
Tompkins: I’m given notes on the people by the producers and that’s great to have, But I try to be as…my goal is to be very present in the interview so I can follow up on something that they say that may not be the point of their story, but it’s interesting and worthy of expanding on—rather than just wait for them to finish the ‘approved story.’ If you want that, you can find that any number of places, but for me to make it interesting to myself and to the audience I want to make it as conversational as possible.
Do you have any guests that couldn’t really lean into that conversational style or you had to bring it out of them?
Tompkins: That’s very, very rare. There’s only one person—and I’m not going to tell you who it is [laughs]—that was extremely difficult to get them to answer anything. It was very strange because it wasn’t just that they didn’t want to answer personal questions, but they seem to think that answering any questions would lead into something they didn’t want to answer. That was a tough one, that was a really tough one. But I kind of enjoyed it because it was a really fun challenge for me to see if I could get this person to feel comfortable and relaxed and not defensive. I felt like there was a lot of defensive that was happening. It was a real test as a host—can I break through to this person?
So if I went through the videos do you think I could figure out who it is?
Tompkins: You’re welcome to watch all the episodes and try!
Challenge accepted! So how much are you guys actually drinking during the show?
Tompkins: I barely drink at all. I take maybe a couple of sips. A lot of the ones that drink will average about two drinks because they have a driver for the hour and so they don’t have to worry about that. But most people will have one drink. A lot of people will have two. Then there are the people that just really get into the idea of, ‘Hey, it’s the middle of the afternoon, and I’m going to live it up here!’
How long do the interviews usually go on for compared to the 15-20-minute episodes we get?
Tompkins: We shoot for a good while. I would say we shoot for an hour or 90 minutes. But it’s a really nice chat. It would be nice or interesting to see the full, uncut interview, especially that guy that was difficult to get anything out of. But it’s a nice leisurely chat and the editors do a good job of sewing it all up and making it feel like an uncut conversation.
For me, watching something like the Jonathan Banks episode, who I typically associated with serious projects—even Community plays off the fact that he’s so serious—I was surprised how loose and funny he seems. Have any of your guests surprised you in terms of you not expecting a certain side of them?
Tompkins: Yeah, he was really funny. I was taken aback by that. He’s a character for sure. And he’s so much fun to talk with. I talked to Bob Saget recently, who was really delightful. Nothing against Bob Saget, but I did not expect to have as much fun as I did chatting with him.
For an audience member, it’s nice to get this great conversation with an actor or creator you love? As the interviewer, what do you feel you get out of these conversations?
Tompkins: The things for me is I want to get an understanding of this person that I either have a preconception of or someone I don’t know and have no idea what their views on the world are. A lot of people, I don’t know their history and where they come from. That to me is what it is—I want to see how we relate as people and how do I get to the person as opposed to just the idea of the person that’s put out on film or TV or whatever. I want to connect as a human being with these people. I leave every interview feeling like I got to know somebody a little bit better. The Bill Paxton one—I didn’t know about his childhood and to hear him talk about his love of movies and the artistry behind it that he got from going to the movies with his dad, it was great to hear him talk about that. Hearing people talk about that stuff always means a lot to me. I always feel like I take away something like that from each of the interviews.
Switching gears a bit, as a comedian, you’ve become known for your very dapper sense of fashion. Was that something you were always big on or was it a later in life type thing?
Tompkins: I always loved dressing up ever since I was a kid. I really got into it in high school. I went to a school where the boys had to wear a coat and tie to school so you had to get yourself a coat and tie and that’s when I really got into clothing.
So it was uniform?
Tompkins: No it was just a coat and tie, so you had to go out and find a presentable coat and tie to wear. We didn’t all dress alike so you had to come up clothes to wear five days a week. I really got into clothing by virtue of that.
So when you came L.A. as a struggling actor was it hard to dress nicely without having the money to do it?
Tompkins: Well, yeah there was a lot of thrift store stuff and a lot of going to secondhand shops and finding jackets that would be good.
As a performer you delve into a lot of different kinds of performing, are there any mediums you’ve wanted to dive into? I know you say writing is difficult but have you ever considered writing a novel or directing your own film?
Tompkins: Directing seems hugely intimating to me because it’s kind the opposite of what I want to do. I would prefer to have fewer details juggling in my head as opposed to more. Writing a book is something I actually feel like I could do. I don’t know when that would happen, but I feel like if the right idea strikes, whether it be short stories or a novel or even a memoir that would be more substantial than most of the comedian memoirs people put out where it’s big font and all the chapters are like ten pages long. Lot of white space in those books [laughs].
One that inspired me lately was Judy Greer’s book [I Don’t Know What You Know Me From: Confessions of a Co-Star]. I was really impressed by how she undertook the task of writing the book and that it was something that had a lot of substance to it. Not just ‘here’s my stories about famous people.’ There were parts about her relationship with her stepkids and being a stepparent—that’s a perspective I’ve never heard people talk about before—what it’s like to suddenly have these kids in your life and try to win them over and feel like you’re doing a good job.
Have you read Steve Martin’s book?
Tompkins: Yeah, I read his book on one cross-country flight. I picked it up at the airport in New York and finished it by the time I got to L.A. It was very well written. That was a good read!
I wanted to also ask about The Pod. F. Tompkast, which you put on hold for a while. Was it just that you got too busy with other things?
Tompkins: Yeah, there was just too much going on. And that’s a real labor of love and it’s a labor-intensive labor of love. It definitely will come back at some point!
Paste: Any definite dates or still putting things together?
Tompkins: Still putting things together, yeah!
Paste: And is that something you always wanted to come back to?
Tompkins: Oh yeah yeah! I really liked it a lot. I think I needed to take a break from it, but I’d like to do it again. I can’t promise that it will always be a regular thing. It might just be a thing I put out every once in a while when there is the time to do it. [Composer] Eban Schletter and I put it together and he’s a huge part of it. It requires a lot from both of us so it’s not an easy thing, but it’s definitely something I’d like to do again.
One more thing I’d like to talk about—one of my favorite parts of the Comedy Bang! Bang! podcast is whenever you come on as Werner Herzog. I’m just curious, where did that come about and have you ever met Werner Herzog since then?
Tompkins: I have not met him, but I’ve always been a big fan. He’s someone I always found to be so entertaining in interviewers or anytime he speaks. He’s just a real character and I love his movies. I think he’s an amazing filmmakers. He’s someone who’s never not interesting. I was listening to a Fresh Air interview with him and his take on things is really dry and funny, but I also think it’s sincere. I really think he means it when he talks about how terrifying it is to look into a chicken’s eyes, you know? Stuff like that is just amazing. I’ll never be as funny as he is just being himself. But it’s fun to do.
What else do you have coming out you’d like to talk about?
Tompkins: I’m doing a third season of No, You Shut Up on the Fusion Network, which is a crazy Meet the Press-style show I do where I moderate a group of arguing puppets, There’s episodes online now and on my YouTube Channel.
Do you get to use the puppets at any point or do you leave that to the professionals?
Tompkins: I leave that to the pros my friend! I am okay just arguing with puppets! I don’t have to be one of them. What those guys do…the puppeteers we have on our show are really incredible. They’re funny puppeteers but they’re also great improvisers. It’s hard to be both, but they really make me laugh. I’m excited to get back to work with them.