Patton Oswalt’s comedy career will be well known to readers of The A.V. Club by now, having traveled from his early days of half-hour specials and occasional TV appearances to a time of a steadily growing audience and hour-long specials to now, when he puts out a special roughly every other year, and it’s always an event in the comedy world. With the debut of his special Tragedy Plus Comedy Equals Time on Epix Friday night, The A.V. Club thought it would be interesting to talk with Oswalt about his career as seen through the prism of the seven specials he’s recorded for TV or DVD between 1997 and now. Along the way, Oswalt tells us about what goes in to pulling a comedy special together, what a good stand-up special director’s role is, and the various specials that inspired him the most when he was just starting out.


HBO Comedy Half-Hour (1997)

The A.V. Club: How does something like this come together? Does the network come to you?

Patton Oswalt: I think at the time it was the network was doing that. Every year, they would do six new specials, and they come to you. Just through you working in clubs and doing TV appearances or just getting some kind of attention, some kind of word gets out about you, and you become one of the six. I don’t really know. I would imagine that the process is that there’s a lot of people in a meeting room who are involved in the stand-up scene peripherally. I know that Gary Mann was there at the time, and he was very wired into what was going on and yeah, that’s essentially how that happened. And I was very lucky to be picked in that group at that time, because there were a lot of heavy hitters in those six, so it was flattering to go, “Oh wow, so, this is the level I’m at right now, because if I’m being picked with these people that means a lot to me.”



AVC: What do you remember about trying to pull together a half-hour of material for that?



PO: Here’s what I remember really specifically, and this is kind of interesting. It was my dream to do a half-hour on HBO, so that was a big deal for me. I know this is such a cliché and other comedians have said this, but I did treat it like a prizefight. I treated it like I’m ready to go in to the most perfect half-hour that I could, and I was doing sets non-stop. In clubs, I just booked myself everywhere leading up to it. On the nights that I had off, I would find a stage somewhere where I could work on a big chunk of it over and over and over again.


So I was taping it on a Friday in San Francisco. Wednesday, I was at the San Francisco Punch Line doing my half-hour, and then I was saying, “I’m going to come back tomorrow night to do it again. Be ready,” and the director took me aside and said, “The sets that I saw you do weeks ago were so good, and the one that you just did was kind of, um, bland, because you’ve been running this so much, you’ve beaten any kind of juice and life out of it. There’s no spontaneity anymore, because it’s almost like you’ve said it to the point where the words are starting to not make any sense. So tomorrow night I want you to go out, go get dinner, go see a movie, forget that you’re doing the special, and then on Friday, when you do the special, I guarantee you, it’ll all come rushing back into your head, and you’ll have a great set.” And I did. So whenever I’ve done a special since then, I work really, really hard leading up to the night of the special, and the night before, I go do something else, and I don’t think about the special at all, and then it all comes rushing back to me the night of the special.



AVC: How do you know when you’re ready? How do you know when that material is all there and set?



PO: Well, in the case of the first half-hour, which is, they kind of picked me, that was me working on it with them until I had a half-hour they were happy with and ready to film, so you just sort of do it that way. My Comedy Central half-hour was also the same way. You work a little bit with them, and then after that, you work yourself, when you’re ready, and then you go to your manager and go, “Okay, I have a new hour. Let’s go out and see who wants to film it.”



AVC: Do you see this as the culmination of the process of stand-up?



PO: It is for me, yeah. That is the culmination of the stand-up portion of my career is. You’ve worked hard enough to earn an hour of stuff that once it’s released, you can never do it again. If you want to stay good, you can’t ever do it again. Then you have to start working on new stuff, and there’s a thrill to that. There’s discipline and risk to what I do, and I like both of those.



AVC: Looking back on that very earliest half-hour, obviously you ditch all this material, is there stuff back there that you still are just really taken with?



PO: There’s stuff I’m very proud of, but if I’m ever looking back into my notebooks for stuff, I would feel like that’s kind of the equivalent of death for a comedian. I’m only looking forward. I’m never, like, “Oh, I’d love to do that bit again.” By the time you see me do it on TV or on an album, I’ve done it to the point where I’m almost done with it and kind of want to do something new.



AVC: What are maybe some moments or something from that first special that you’re particularly proud of?



PO: I still have a lot of affection for “The Magic Of Oil Painting” bit. Even though it basically devolves into sustained screaming, it’s this character that I kind of liked, this crazed, German, Klaus Kinski-style person who doesn’t realize he’s spitting some pretty dark poetry about his life while he’s trying to teach you how to paint. I like that bit a lot. That was one of the first, “I’m being loose enough I can just kind of fuck around onstage right now.”

Comedy Central Presents (1999)

AVC: Comedy Central has become such a home for breakthrough stand-up talent, and yet it seems like that form gets pushed further to the edges of the channel. What are the venues for stand-ups to break through now versus then?



PO: Comedy Central still does half-hours, but I think the venues now, it’s more ethereal. You’re there more as a commenter on things like Twitter, on YouTube, on Tumblr and Instagram—and how can you make your personality come through? There are people breaking really big on Vine now. They’re basically doing little brilliant six-second short films on Vine that I love. If anything, it’s become more focused and narrowed and more laser-like of, “How do you make an impression with this much words or this many seconds?”



But in a way, that’s nothing new, because back in the day when you wanted to get on TV shows and audition, your audition was never more than four minutes, and there were people who were like, “Ugh, how do I do it in four minutes?” Well, now you have to do it in six seconds or 140 characters.



AVC: This was your second time through. What had you learned from your first time through that you really applied and sharpened these next times?



PO: Well actually, my Comedy Central half-hour is an example of me then, because my first half hour was very successful, I got a little arrogant, and I got a little full of myself as to what I was going to try to do. I was going to try to break the format a little bit, and I was fighting a lot with Comedy Central. I wanted to do a thing where, because they had commercial breaks, when they came back from each break, I would be finishing a joke, but you would never hear the beginning of it. You would just come back from the commercial break, and I would just go, “And that’s why Count Chocula’s pro-life,” and I would tell the audience, “Just cheer for no reason.” They fought me on that, even though I filmed it that way. They then cut that out, so that really stunk.


Also, I didn’t have enough of a… It was a combination of arrogance and terror, where I want the stage set to look a certain way, and it was really elaborate and it ended up looking like dog shit. I wanted to make it look like the opening of a little rep theatre, but the poster was too small, and you can’t figure out what the fuck it is. It’s just this weird thing on an easel. It just doesn’t make any sense. You just gotta have one simple image.

Then I also let them kind of boss me around a little bit, where they were saying, “We want you to come up out of the audience. You gotta come up out of the audience.” And I was like, “Uhh, I’d really rather not do that,” and they insisted on it so I let them do it and it was a terrible way to introduce yourself. They had me standing in the middle of the crowd for like 10 minutes while they were setting lights and everything. You’re just this weird, fidgety guy, and you walk up, and there’s no, “Oh wow, the performer just appeared.” They’ve been staring at you. One of the audience members was yelling at me, saying, “Hey, it’s her birthday here. It’s her birthday. Can you do something when you go up?” I’m like, “Well, I’m… I’m taping a special. I’m doing a half hour.” And he goes, “Well fuck you, man. Just mention her birthday, asshole.” Then I was trying to look around for somebody to get rid of the cable, but then I thought that would make it even more disruptive. Everything was bad. I didn’t speak up enough to go, “Hey, no, I’m not doing that.”



But then I also ground my heels in on some really dumb stuff. My material was kind of in a transitional period between—if you watch my first half-hour there’s no vulnerability to it. It’s all about, “I’m telling you what it’s like. Here’s how things are. Here’s something stupid: isn’t that dumb?” In my Comedy Central half-hour, I’m making the transition to talking a little bit more about myself and have a little more vulnerability but it’s still this weird mutant. It’s not quite there yet.



AVC: How do you handle things like audience management when you’re taping a special?



PO: Well, that was the only time that I had that, because I didn’t assert myself enough to go, “Well, I’m not coming out of the audience that way.” Any other time, if you set the thing right, which is, “Hey, we’re taping this. This is a big deal.” You have a really good opener that you like. And it’s pretty great. The audience, they end up rooting for you and they get as excited for you as anything else. That’s what’s great.



AVC: Comedy Central and HBO are still the big homes for stand-up on TV. What are your thoughts on their separate approaches to the form?



PO: They’re pretty much both meat-and-potatoes approaches. They put someone in a theater, and they tape the special. I was really happy when HBO, this past season, did the Sarah Silverman special, which was much, much smaller. And I’d like to see more comedy specials happening in a more intimate venue like that than in these giant stadium things. Stadiums and huge cavernous theaters are kind of anti-stand-up. So it’ll be interesting to see if they let people do more stuff like that.



AVC: When you were doing these very early specials, what were some of the great specials that you looked at as, “I’d really like to do something like that?”



PO: Obviously, Chris Rock’s Bring The Pain was a big deal for me. Dennis Miller’s Black And White, I thought was a fantastic special and that was a, “Hey, I’m going to try something kind of interesting here.” I remember Bill Hicks’ very first HBO half-hour was great, the way they put it together.


There was one, I think maybe Showtime did this, but I can’t be sure, but Jeff Altman did some special where it’s a first-person point of view of a guy doing a stand-up special, and it’s at the awful little one-nighter where everything is going wrong. And it’s really interesting. I think you see his face once at the beginning when he’s looking in the mirror, and then he goes out, and it’s all from his point of view. It was pretty cool. That’s on the far edges of, “Oh wow. I don’t know if I could do that,” but it was good to see that somebody was willing to mess around with the form even that far back.



No Reason To Complain (2006)

AVC: What’s the difference, other than just time, in preparing an hour-long versus a half hour?


PO: Yeah, there’s a difference in you’ve got to sustain much more stuff, but No Reason To Complain is a weird beast because I put out my first album [Feelin’ Kinda Patton] on United Musicians, and it was very well received. Comedy Central really liked it, and they offered me the hour special almost immediately. And I said, “Well, if you could give me like six months, so I can develop… I don’t want to do any of the material that’s on the album,” and they said, “Oh no, we want the material that’s on the album. That’s what we want in the special.” I said, “No. I don’t want to repeat stuff that’s on the album in the one-hour special. That’s really lame. I want to do all new stuff.” So we fought back and forth, and they ended up giving me three months.

So that special is half stuff that was on my album and then half new stuff. I was able to work up a half an hour of new stuff before I had to go on and tape it. I guess in the end, it was lucky that I had the transition to doing a one-hour where I was still forced to do a half-hour of my old stuff. If they had given me another three months on top of the three they gave me to prepare I could have done a fresh hour, but then who knows? Maybe that wouldn’t have gone as well. I had a couple of bits I knew were working, and I knew how to do them along with the half an hour of new stuff. So that was like the transition special between doing a half-hour and doing an hour. I just really wish there wasn’t any material from Feelin’ Kinda Patton on that special. It just makes me feel cheap.



AVC: What’s the process of network notes or working with producers and directors on something like this?



PO: The process is the same process as anything else: They have to become confident with you over the years. So when I was first doing my half-hour it was, “Let’s do a transcription and submit this, and let’s talk about it.” Then the Comedy Central thing, there was some fighting back and forth, and then the hour there was some fighting and compromising going on. By the time I hit my second hour—that was where they were confident enough in me, like, “Well, he’s done two half-hours and an hour. We probably don’t need to mess with him that much.” And then by the time I did this latest hour, that was, Bobcat [Goldthwait, the director] was basically saying, “I don’t want anyone talking to you. I just want you to be left alone. Do whatever. You don’t need to submit anything. We don’t need to read transcripts. We know you can do this.” But unfortunately, you have to kind of earn that. They have to see that you can pull that off several times before they go, “Oh, okay. This is okay.”



AVC: Was there material in some of the earlier specials that was either cut or the network wasn’t comfortable with that you either fought to get through or you wish had been on there?



PO: I wish they had let me do the format thing with the half-finished jokes on my Comedy Central half-hour. That’s still very frustrating to me. Because they just let me do it and then cut it out without telling me, and that made me really, really pissed off.


Maybe there was something when I did my first half-hour but I kind of agree with this note, which was: I had this one joke that was, “I like my women like I like my coffee: tied up in a sack and thrown on the back of a donkey by Juan Valdez.” And the director said, “That’s a perfectly okay joke, but everything else you have comes from some place kind of personal, even if you’re not talking about yourself personally, it was your personal feelings toward something, and that’s just a joke-joke that you don’t feel either way about. It’s just a clever thing to say. And it really sticks out. It doesn’t really fit with the other stuff.” So he was saying you might want to not do that. Now, I can’t remember if I cut it or not, but I remember that note was also really interesting. “Oh, okay. Do these jokes come from any place you care about or is it just, ‘Look how clever I’m being!’?”



AVC: There’s obviously been such an evolution of you, both as a comedian and just as a person. When you look back at the guy who taped the early specials, what do you see as the biggest difference between him and you, just professionally?



PO: He was still studying for the test, rather than comedy was an ongoing thing in his life, and he has decided to stop along the way and drop an hour. That was the last time I was on someone else’s schedule. For the HBO half-hour, the Comedy Central half-hour, and then that first Comedy Central hour, that was, “You’re doing this on this date. Now get ready.” Everything after that was about, “I’m ready. Now who wants to tape this?”



AVC: You’re kind of this character who evolves across all of these specials, and some of the material at this stage was about how you never wanted to have kids, and now you’re a father. How do you feel about presenting that evolution of your own psyche and self just out there onstage?



PO: See, I love that. I never thought of myself as presenting a character, I was always being, “This is Patton Oswalt in 1997. And this is him in 1999.” And you can watch it and go, “Oh, see how he’s changing. See how this opinion that he was so almost dismissive about, like, ‘I think I know what’s what,’ and then you see him a few years down the road, and he’s going, ‘Oh well, I was wrong about that.’” And you see people kind of embracing, not only new experiences, but you’re also embracing the experience of you completely changing and reversing all your valances.

No one is more dead set on what life is than people in their 20s and 30s. It’s not until you get into your 40s when you’re like, “I have no fucking idea. Are you kidding?” But you have to work towards that. I guess I’m kind of gratified that that evolution of my life is on film somewhere. It’s recorded. You can say that the Patton from the HBO half-hour would annoy the Patton from


Tragedy Plus Comedy Equals Time. I even talk about that a little bit when I get to Tragedy Plus Comedy Equals Time, I invoke that 20-year-old, lecturing people about music. [Gruff voice.] “Let me tell you something about Nickelback…” and then the 44-year-old me goes, “Eh, let me ask you something about…” so I can keep both those personas in my head.

An Evening With Patton Oswalt (2007)

AVC: So An Evening With Patton Oswalt was packaged with the Werewolves And Lollipops CD. It seems like they evolved together. How did you come to that decision?


PO: Yeah, that was Athens, [Georgia], at the 40 Watt. I just wanted to do a little extra bonus of “Well, here’s the album where it’s all solid and complete, and this is what the process was like to get there.” I think I wanted to maybe demystify a little bit what I did, because I think that was around the time I was doing a lot of Comedians Of Comedy stuff, and there was just this whole new wave of comedians coming up, and I was like, “If there’s anything I can put out there that shows people this is just work, like any other job. You gotta put in the work and you can do something great if you just show up and do it.” So I think that was my motivation behind that.



AVC: Comedians Of Comedy was this central point of your life for a while. How did that affect your stand-up?



PO: Oh, it helped it immensely, because I was working with people, with Zach [Galifianakis] and Brian [Posehn] and Maria [Bamford] and then later with Eugene Mirman, that were so good, so creative, and messing around with the boundaries of what stand-up could be, and I think that’s what drew them to me—and I wanted people around me that were funnier than me that would make me work harder at what I did and not just settle for keeping people around me where I’m the funniest guy in the room. It was so much better to have people who were constantly challenging me, who were funnier than me all the time. I think that’s where that came from. It was for very selfish reasons. I wanted to watch these guys. I was such fans of theirs, and I wanted to improve what I did. So you put better comedians around you.



AVC: How do you choose which venues to film at?



PO: You call them up, and you ask them. I was lucky that I had built up enough of a relationship with the 40 Watt. I did my first album there. I always return there to get ready for new albums. This was my second album coming out so I just asked them, let me go and do two shows and prepare them in. That’s kind of the place I go to prepare all the time for all my specials and stuff.



AVC: What makes that the place you go to, to prepare?



PO: Because it’s very raw, and you have to keep an audience’s attention that’s standing up. It tells you how good or bad you’re being.



AVC: What are some other venues you love or love to try out material in?



PO: I love going down to the Irvine Improv because it’s this comedy club in a strip mall. It’s so anti-theater. It is a comedy club, and you are kicking against people with some very narrow views of what stand-up should be and it’s good to fight against that. It helps you edit. It really helps you edit. On the other hand there’s the Largo, which helps you write. So I’ll always love going to the Largo. Then there’s just places out on the road. The Acme in Minneapolis, Helium, Cobb’s in San Francisco, all those places I just love. They’re comedy clubs, but they’re a little elevated and smarter.



AVC: As a comedian, do you prefer that process of writing or that process of editing?



PO: I don’t prefer either one. They’re both very necessary. I just prefer the process of going onstage and working out new stuff.



AVC: When you’re preparing one of these specials, how do you choose what order material goes in?



PO: I don’t. It kind of chooses itself. I know that sounds very hippie-dippy, but you just kind of keep talking and doing sets and it’ll let you know where it belongs in the set.



AVC: Especially with things like the “Black Angus” routine and “Famous Bowl” routine, it seems like you broke through to a larger audience. What was that like to suddenly have that expansion, if you felt that way at all?



PO: I don’t really know if it made the audience larger, but it certainly filled the audience with way more fans. And fans are a good and bad thing. Actually, fans are a totally good thing, because you have people that are there to see specifically you, and they want to see what you do. But they also don’t want to see you repeat your old stuff. Maybe, occasionally, they brought a new friend there, so there’s one bit they want you to do or one of their faves, but you can’t please the whole crowd that way. When you have fans what you want to get them used to is, “When I go to see this person, they will always be working on new stuff for me to look at.”



AVC: Now that you have some of these routines that you’re so well known for, do you have people who don’t necessarily understand that you don’t repeat that material, who still want to see it or hear it?



PO: If I do, I don’t really hear from them. Occasionally I’ll see them in a comment thread, saying, “Why didn’t he do this bit, why didn’t he do that bit.” But I can’t focus on those people. That’s not what I where I want to go with my career, so ultimately, that doesn’t affect me.

My Weakness Is Strong (2009) and Finest Hour (2011)

AVC: You were really delving into some far more personal stuff than you had before. You’d always done personal stuff, but this got into things like your depression. Was that a conscious choice or was that the way you’d always been moving?



PO: I think it was a split between it being a conscious choice because I was watching people like Louis C.K. and Maria Bamford that were being so incredibly personal and hysterical. But also, it was an organic thing. It was organic from becoming so comfortable onstage after doing it for so long that I was able to delve into those things. But that literally just came organically from time.



AVC: Was there a fear almost of presenting that material, or did you feel like you were ready to talk about that?



PO: I felt like I was ready to talk about it. I had been doing it onstage in clubs and on tour for a while, and at that point, I was pretty comfortable with the idea of, “I’m just going to lay it all out and be way more…”—not lay everything out, but be way more open and raw. Just getting comfortable with the rawness. But again, it was all organic through time. I knew it was ready because of all the time I had done it onstage before that, before I came to the special, when I was out touring.



AVC: Is there a line between what’s too personal and what’s suitable for stage?



PO: I don’t think you develop that. I think it develops itself. It’ll tell you what you put out there and what you don’t. It’ll happen without you being able to describe it. I wish there was a better answer, but that’s just the reality of it.



AVC: So at this point in your career, you were playing these specials in larger venues, how does that affect the process of pulling one of these together?



PO: It’s still the same process for me, even though the venues may be bigger. The stakes are a little higher. There’s more equipment and more cameras. It’s still the same process of you go onstage a lot and you work it out on stage until it sounds natural and then you just go up and do it.



AVC: Do you try to be aware of the cameras and directors?



PO: I tune them out. Again, I tune them out from my years of having been on TV. Doing TV spots and Evening At The Improv, that also helped. It was doing all those cable shows all throughout the ’90s. I kind of don’t see the cameras anymore.



AVC: You’ve always done political material, but you do a little bit more of it in these specials. How do you work that into the routine?



PO: Again, it’s not a conscious thing that I do. It ties in with the larger personal stuff. When I’m talking about political stuff, it’s the idea that I’m so frustrated that I can’t avoid this political stuff that’s affecting me personally and affecting me emotionally, so that’s where that comes from. Like any other internal or external thing, that’s goes along with it. But I don’t look to go, “I want to do this much political stuff.” If something grabs me, then I go with it.



AVC: Have you ever been warned away from political stuff by a network?



PO: Not that I remember, no. I’m not doing these specials for networks. I do them for myself and we see who wants to show them. It’s not like I’m talking to the network anymore.


AVC: Was there a time where you really wanted some network to show a special, and they weren’t interested?



PO: Yeah. I’ve had some stations, certain networks, pass on it, and it’s been very frustrating, but again, I’m always going to be doing specials, so I can’t look at it as, “Okay, this didn’t work. That door is shut forever.” And also, every couple years, you do a new special; there’s new networks. There’s new venues. That’s constantly, especially now, changing. So I can’t get hung up on one network or another.



AVC: At this point, you’re at a clip where you’re doing a special every two years. What’s the life cycle of one of these look like at this point in your career?



PO: I try to do a special every two years and then in the year between I try to write a new book. So the whole cycle is when I’m not writing a book, I’m out doing stand-up.



AVC: Pulling this stuff together, how long does that take between starting the process of it and finally getting to filming?



PO: About a year.



AVC: How much material would you say you go through to get to that hour of stuff?



PO: Easily two-and-a-half hours that I keep jettisoning and throwing away. Stuff where I like it, but it doesn’t quite work.

AVC: How many different stand-up sets do you do in that time?



PO: Oh man, I’ve never counted. About a year’s worth. Average it out, I don’t know.



AVC: When you’re pulling together this material, when do you know you’re ready?



PO: You know when you know. At this point, it’s not a thing I can describe anymore. I just know.



AVC: From earlier in your career was there a moment where you felt that, you were just struck by it?



PO: Probably when I was doing My Weakness Is Strong is one of the first times I felt like, “Oh. Wow. I have a special right now that’s ready to go. Let’s do it. Call up my manager. Okay, let’s see who wants to do this.”


Tragedy Plus Comedy Equals Time (2014)

AVC: When you look at the guy who filmed that versus the guy who filmed that HBO special, what do you think are the biggest differences?


PO: The biggest difference between the guy that did the latest one and the guy who did the HBO one is he is, I’m trying to prove something to myself, whereas in the HBO thing, I was trying to prove something to this amorphous idea of what I thought show business was and who I thought the gatekeepers were. I’m not as present and aware as I am when I’m doing Tragedy Plus Comedy Equals Time. I’m trying to prove more quiet and internal things to myself, and I have a much longer view of my career at this point. I still had that mentality when I did that half-hour, “You’ve got one shot and this is it…” Now, I have more of a life is long kind of feeling.



AVC: What challenges do you set for yourself now when you set out to do one of these?



PO: Can I unveil an actuality? That’s the abiding one for me: Can I unveil an actuality? That’s the thing that I want to keep trying for.



AVC: This one’s directed by Bobcat Goldthwait. What was it like working with him as a director?



PO: It was as great as you think it would be. You’re being directed by a former stand-up that has done many, many specials. One of his specials, Share The Warmth, was another big influence of mine when I was doing my first specials. That was another big abiding influence. And he knows what a comedian thinks and what their process is leading up to doing the show, so he was already in tune with me in terms of “Keep this person away. Don’t ask him this. Don’t ask him this. We’re just focusing on these other things.” I really had someone in my corner.



AVC: Was that the first time you’d had another stand-up direct one of your specials?



PO: That was the first time. The closest I had before was Jason Woliner doing Finest Hour, and he does a lot of comedy and knows a lot of comedians, so it was great having him there too but Bobcat was an entirely different animal in terms of, “I know exactly what you’re thinking right now,” and he was always right.



AVC: What’s your relationship with the director like on one of these?



PO: My main objective is to have him give me the least amount of stuff to think about outside of the set. That’s what the best relationship you want with a director is, and that’s what Bobcat gave me in spades.



AVC: As you look back at your career and all of these specials, are there one or two in particular that really stand out to you as you were really happy with how they turned out?



PO: The two that really stand out for me are the very first one because that changed a lot of stuff. That changed a lot of how I was perceived by other people. And then My Weakness Is Strong, because it changed how I perceived myself, how I perceived what I could do and what I could execute, versus what I could conceive. So those two are always big signposts for me.