Hailing from Philadelphia, Paul F. Tompkins first came to national prominence as a writer and occasional performer on Mr. Show With Bob And David, the HBO sketch series that also introduced Bob Odenkirk, David Cross, Sarah Silverman, Jack Black, Brian Posehn, Mary Lynn Rajskub, and Tom Kenny (among others) to the world. A stand-up comedian with several albums and specials to his credit, Tompkins is also a fixture on the podcast circuit, having introduced a full cast of characters to the Comedy Bang! Bang! universe and joining the cast of Superego for its upcoming fourth season. In addition to hosting in the Jim Henson Company-produced talk show No, You Shut Up!—in which he discusses topics of the day with a band of raving puppets—Tompkins also fronts the webseries Speakeasy, which finds him interviewing fellow entertainers over cocktails. (And, periodically, challenging them to Internet-themed games.) The latest episode, featuring Breaking Bad’s RJ Mitte, is now available via the Made Man YouTube channel.

The A.V. Club: It’s a bit strange asking you this first question, since you’ve already done a whole special and album on the subject. But…

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1. What’s the worst job you’ve ever had?

Paul F. Tompkins: Telemarketing, which did not make it into the special, because there was just nothing funny about it. That was absolutely, hands down, the most miserable job I ever had. Everyone hates you. You hate everyone. All day long people are getting mad at you, hanging up on you, and you’re working on commission so you have to just keep calling, calling, calling to make as much money as possible. That was the one job I think I’ve ever had that I quit without any notice. I didn’t tell anyone. I got my last check, and I just walked out of the building.

AVC: Was there any particular breaking point, or did it become too much and you just had to walk out?

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PFT: It just became too much. I had been working there for a while, then went home for Thanksgiving. This was not long after I had moved to Los Angeles. I didn’t know a lot of people here. So I went home, saw my old friends, and then came back and realized “Life is too short for this. I can’t be here anymore.” It was the most dehumanizing job I ever had.

AVC: Was there at least some form of camaraderie among the call center employees?

PFT: Nope! There sure wasn’t. It was a bunch of old people who were looking to fill their days, a bunch of high school kids who had this as an after school or summer job, and then me, who was the person who was just trying to pay my rent. There was one guy that was kind of friendly, and he was smarter than I was, and he got out of there really quick. But I had one work pal for about a month.

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AVC: It seems there was a bit of a sinister hiring policy going on there: Who would want to hang up on a high schooler or a senior citizen?

PFT: Oh, I think anyone wants to hang up on someone who sounds as inarticulate as a high schooler or who sounds as doddering as an old person. In both scenarios, you feel like this is going to take way longer than I want it to take. And I was actually pretty good at it, because I was able to perform the script better than most people, so I sounded more engaging, and I was able to keep people on the line more. Actually, I made more money on that job than I did any other day job, but I just couldn’t take it.

2. What did your parents want you to be?

PFT: I have absolutely no idea. That’s frustrating for someone who is a performer. I was always given the impression that they didn’t think I should be doing that, but they did not offer an alternative. I think a lot of people that go into performing, their parents are very clear on what they think would be a better idea, but my parents were not.

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My mother especially let me know that she thought it was pretty much a waste of time. She did once suggest that I take piano tuning lessons from my uncle who is a professional piano tuner and repairman. This is well after I’d been making a living in show business. I think it was the second season of writing on Mr. Show. And I said “Why?” And she said, “Well, it’s good to know a skill in case you have to fall back on that.” So even after it was working out, she was not convinced it was going to work out.

AVC: That was the type of conversation that just wasn’t had in the Tompkins household?

PT: Yeah, there was no real conversation. When I was a kid and I said I wanted to go into performing, my mother tried to talk me out of it, was very upset, but never ever gave me an alternative. So it was like, hey you can be whatever you want, just not that.

3. Who would be your pop culture best friend?

PFT: I like to think that I would get along well with Cat Deeley, the host of So You Think You Can Dance. My wife and I watch that show, and we talk about that all the time: That we think that she would really like us and that we would have a lot of fun together.

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AVC: Any particular reason, or is it just the way that she presents herself on the show?

PFT: It’s the way she presents herself on the show. She seems very down to Earth and like she likes to have fun, and so we imagine we’ll be in Palm Springs, hanging out with Cat Deeley.

AVC: She is the best of the reality competition hosts, in terms of coming across like an actual human being. She seems the least jaded and the most enthusiastic about the contestants. That’s true of So You Think You Can Dance, in general.

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PFT: Yes, absolutely. I totally agree. I think that show is very honest, and there’s not the same cynicism that comes off in ways of, say, American Idol.

4. What game show do you think you’d be good at?

PFT: I think that I’m okay at Jeopardy! I don’t know if I would ever be able to make it on the show, because apparently the test to get on the show is way harder than the show. So they want to weed out people who are going to freeze up or lose their mind on television. So if you can pass this test, then you can pass the somewhat easier questions that we’re going to ask on the show. But I bet I’d blow it. I don’t do well in those situations. I tend to panic and freak out. If I’m watching on my own, I feel like I can ace anything, but in front of other people, I feel like it really falls apart. Even something like Wheel Of Fortune. I think if I would be on that show, I would look really dumb. I’d look really, really dumb, even by Wheel Of Fortune standards.

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AVC: And you think this despite your performing background and improvisational skills?

PFT: Yeah. If I’m doing stand-up, if I’m on a stage performing, I’m in control of what I say, and it’s a totally different vibe than “Hey, add these numbers!”

One time, I was watching a magic show at The Magic Castle here in Los Angeles, and a guy called me up to help him with a trick and I was freaking out. I did not want to do this at all. It’s my greatest fear: There’s nothing more awkward for me than doing something like that. And on top of that, I had to do addition. It was something that involved very rudimentary math, and I was asked to add a couple numbers. And I did it, and the figure came out of my mouth and I immediately doubted it. I was like, that’s wrong. I swear everyone’s going to find out that I am a functional illiterate. Somehow I’ve managed to get around and put clothes on, but I don’t know how to add numbers or what they look like really.

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AVC: Was the math the misdirection in the trick? What did it add?

PFT: Oh, I don’t remember what the trick was. I don’t remember what happened. All I remember was that moment where, in front of a room full of adults, I was asked to add a couple numbers together.

5. How would your enemies describe you?

PFT: I wish that wasn’t so easy. I wish there wasn’t a million words that come to mind. I like to think: formidable. “Nicer than me” is what an enemy might say. Too nice.

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6. If a deli named a sandwich after you, what would be on it?

PFT: Peanut butter and jerky. Your choice of bread.

AVC: What bread would you choose, Paul?

PFT: Me personally, Kaiser roll, all the way.

AVC: One piece of jerky or jerky spread out as if it were a deli meat?

PFT: Hey, man. That’s up to you. How are you feeling that day?

AVC: I’m feeling I should spread the jerky out.

PFT: Yeah. There you go. Pile it high.

AVC: Crunchy or creamy peanut butter?

PFT: Look, I don’t have time to wait on you all day. We’ve got a big line behind you.

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AVC: Fair enough, fair enough.

PT: All jokes aside, creamy peanut butter. Crunchy peanut butter—people that like that are demented. If you like crunchy peanut butter, you hate your soft palette and your gums.

7. What was your first big, grown-up purchase?

PFT: It was a new television. This was in 1995, and I had gotten a good paying job on a TV show. And I went to Circuit City and got myself a brand new television. At that time, the biggest television I’d ever owned, and it was an old tube TV that fit in a hutch, so it’s not like it was a big TV—but by the standard of the time, it was certainly something. And I was thrilled. I couldn’t believe it. That it was in my home, in my little apartment. A Zenith television. And it had a timer on it, so you could time it to go off and come back on again. There were more than four settings on it in terms of the picture and stuff like that. It was very exciting.

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AVC: As an employee of an HBO show, did you get a free subscription to the network? Were you able to watch Mr. Show on this TV?

PFT: I did get cable. It was not for free. I paid for it, and I must have watched Mr. Show live as it aired at least once. But back in those days, it was Fridays at midnight. And I was a young man and I had drinking to do, so I was probably out on the town. And if I was lucky, I remembered to put in the VCR Plus+ code to make sure that I got it recorded.

8. What’s your go-to karaoke song?

PFT: I would say “American Girl,” Tom Petty And The Heartbreakers. There’s a tiny bit of audience participation that people always enjoy. Another great one is “Secret Agent Man” by Johnny Rivers: Uptempo, driving beat, amazing guitar lick.

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AVC: Do you try to keep your karaoke selections separate from what you would perform in Varietopia?

PFT: Yes. Although that said, I have performed “American Girl” onstage before, but after years and years of doing the show.

AVC: And a perfect song for an audience—what’s the call-and-response portion that you do?

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PFT: “Make it last all night.” It’s that second “make it last all night” that people love to jump in on. But yeah, people love that song. They get excited, because when that opening guitar riff comes on, people recognize it immediately and they really like it.

9. What’s the worst living situation you ever had?

PFT: When I first moved to L.A., I did not have a place to stay. A friend of mine who was here—a guy that I had lost touch with I didn’t realize was in Los Angeles, and we got in touch with each other. And he said, “Hey, you can come crash with me and my girlfriend. We’re going to be leaving here soon anyway. You can just take over our apartment in this building.” And so it was my buddy Brian and his girlfriend. The idea was that this would work very well. I lived there in that one-room apartment with them for, I think, about four months. And of course, the girlfriend grew to hate me, just hated me. At first it was, “I think you being here is going to be really good for Brian.” And then by the end, we just were not speaking to each other. And I would always feel bad about it. But then I would always eventually remember, but wait, he told me they were going to be leaving, literally any day. Like any day we’re going to be out of here. And I was there so long, eventually another apartment opened up in that building, and I moved in there, and then they moved out I think another four months after that. So it was not entirely my fault, but certainly I should have had things a little more together to prevent that from happening at all.

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10. Who could you take in a fight?

PFT: Any child under 13.

AVC: But after 13, they’re too scrappy?

PFT: After 13, I think they turn into teenagers, and they get all sinewy, and they have their weird strength from their teenage anger and their body’s changing. But yeah, any child under 13.

11. Do you have anybody’s autograph?

PFT: I have Peter O’Toole’s autograph on a first-edition copy of his autobiography that I acquired under false pretenses. I wrote about this on my Tumblr, and it’s there if people want to find it. He came to Philadelphia to do a signing of his first book, and I lined up. He was my favorite actor of all time. So I went to get his autograph, and at the time I did an impression of him in what passed for my standup act at the time, and it was him doing a dramatic recitation of “The Itsy Bitsy Spider.” And so I was determined to get a part of a quote from “The Itsy Bitsy Spider” and then his signature. And very early on in the signing, I think after about 10 people—it was a big long line, tons of people showed up for this—the handler from the bookstore said, “Well, he’s getting tired, so he’s not going to have time to personalize all the books.” So I came up with a lie that my late father used to do this impression of him when we were kids that we always loved. And it would mean so much to me if he would write just a little bit there. My father was very much alive and never did impressions of anyone. And so [O’Toole] said, “I’ll just write ‘up comes the sun,’” and I said, “That is fine.” So I have that book to this day.

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AVC: Had you rehearsed what you would say to him in order to get “The Itsy Bitsy Spider” part, prior to making up the father story?

PFT: Yeah. I think it was pretty much the same thing, except I was going to put it in first person and say I’m a comedian and blah, blah, blah. But yeah, once I heard that I was not going to get this, I instantly resorted to lying. And then the worst kind of lie really, to say my father was dead.

AVC: Did you tell your dad after the fact that you had used him in this way?

PFT: I did not, but it was printed in the Philadelphia Daily News. They had a little story on the signing because it was the biggest signing that they’d ever had at this store. I think it was a Barnes & Noble, and it was the biggest book signing in the city that they’d ever had, and at one point it said the fans words were moving in their obvious sincerity. And it was like these three quotes and mine was the third thing. “My dead dad, to see this impression of you.” So I lied to my idol, and it was printed in the paper.

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AVC: Did you keep a clipping of that article?

PFT: I did. I have it somewhere. I’m going to dig that up. I’m going to find it. I know I still have it somewhere.

AVC: Seems like it’d be a perfect thing to keep with the book.

PFT: You know what? You’re right. And maybe that’s where I should put it.

12. Bonus question from Riki Lindhome and Kate Micucci: When Paul F. Tompkins wears sweatpants, does he feel like Clark Kent?

PFT: Oh yeah. And you know what? It’s exactly the same effect too. I have had people that I’ve been acquainted with for years walk right past me if I’m in gym clothes. It’s hilarious. I will look right at them, and as I’m opening my mouth to say “Hi,” they just keep walking. And I realize they did not register me as someone they know, just another human being on this planet. It’s an amazing thing.

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AVC: When did you start taking such care in your wardrobe?

PFT: Since I was a little kid. I always liked dressing up. I think, because I always liked performing, I always liked costumes and things like that. I went to a Catholic school: We wore a uniform when I was in grammar school, and when I went to high school, boys had to wear a coat and tie. But it was up to you what you wore, as long as you were wearing a coat and tie. That’s when I really got into clothes and finding stuff that I like. I enjoy very traditional stuff, and I enjoy kind of outlandish stuff, and I just really like clothes. I always have.

AVC: Is it something that you’ve studied at all? Have you read up on fashion history, or what kind of patterns go well together? Or is it just to your eye?

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PFT: Yeah, it’s just to my eye. And I think there’s hardly any middle ground with men’s clothes. It’s either men think it’s ridiculous: Like why would you wear a suit if you didn’t have to? If you’re not going to a funeral, why would you ever wear a suit? And then the other side of it is this extreme pedantry of, “these are the rules of fashion.” It’s supposed to be fun. I have people lecture me sometimes online. They don’t want to give me advice; they want to tell me what I’m doing wrong. They don’t like the knot in my tie, or my pocket square and the tie are too matchy-matchy—or they’re not matchy-matchy enough. And it’s just like, who cares?

I used to get hung up on that stuff, and then there was a conversation I had with somebody about the bottom button of a vest: if you button it or not. And the number of buttons dictates whether or not you button that bottom button. And then I realized this is all ludicrous. I don’t want anybody saying this stuff to me. I’m not going to say it to anybody else. I have a friend who only buttons the bottom button of his suit jacket, which you’re not supposed to do. “Supposed to do.” But it’s his thing, and it’s his personal style, and it’s like you’ve got to honor that. People can do whatever they want. It’s putting all these rules on ridiculous things.

If you’re going to tell me about my tie and my handkerchief or whatever—we’re talking about strips of cloth. We’re talking about the rules governing these absolutely superfluous strips of cloth that we are adorning ourselves with. So you’ve really got to take a step back and say, “Who cares?” And also, what’s great about the time that we’re living in now is people can wear whatever they want. I don’t want everybody to dress like I do. I don’t expect people to do that, and I don’t think it’s a shame that they don’t. I think everybody’s entitled to have their own style, and it’s great that we live in a time when you can do that.

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What question would you like to ask the next person?

PFT: When was the last time you cried?

AVC: That’s a good one. When was the last time you cried, Paul F. Tompkins?

PFT: I think probably a year ago, I was really down. I was having a tough time. I was very depressed, and it was one of those moments in your life where you just feel like, man I don’t have a handle on anything. I don’t know what the fuck I’m doing. And life is really hard to navigate. It was just pure tears of frustration. I was all by myself, and it was one of those things where I felt it coming and I was like, yeah, let’s let this happen. Let’s bring this on, and it’s got to help even a little bit. Which it did, a little bit.

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