Paste: Why did you decide to record the new album in Massachusetts?
Gondelman: It was a fortuitous set of circumstances. I had my book come out in October, that I co-wrote with Joe Berkowitz. It was a long push to get the book out and it was out and we did a few live author events. That may have been my biggest moment of “Now what?” The book process, not just the writing but the promoting and the pitching and waiting for the contract to come in took two years so it was two years working towards this thing. Even if it wasn’t every day, it was always there in the background. When the book came out, and we were done with that promotional push over the first couple of weeks, it was a real big “Now what?” I knew that I had a pretty strong set of stand-up that I had written since the previous album and I had some time off from work coming up, so I was going to go out on the road a little bit. My friend Dan Boulger had just recorded an album, which hasn’t come out yet, at a monthly show in Somerville. My friend Ryan Donahue who had offered to have me on the show before was, like, “You want to record your next album. What don’t you come record it at my show? We draw a little crowd. You’ll draw some people.” It worked out really great. That room was perfect. I thought I would just try to swing for the biggest venue I could comfortably fill and try to record in one show rather than doing just a few shows at a smaller venue for safety. Because if it doesn’t go well, I can do a couple of shows at Union Hall, which is my home base in New York. But I had some time off work and I had this offer of this really great performance space. Dan, who had recorded the month before, was, like, “You’ve gotta do it here.” It all lined up really well.
Paste: And you did it at only one performance. Usually, most stand-up recordings are done over the course of a weekend, cobbling together the best versions of the material from those five or so shows.
Gondelman: I’m trying to be less anxious about getting every single thing right. There were a couple of jokes that, just because I had only been doing them a week or two, weren’t ready so I cut them out. There were other things that I could have done slightly better but it’s a live show and it feels like a live show. And I like that. And I like not feeling too edited. You kind of feel it in the rhythm a little bit. Not that it’s bad, but I thought the priority was to get this into the world. And there’s very little pressure for me to have a flawless album because I’m only being judged against…well, maybe nothing at all. It’s not like when a more established comedian puts out a special or a fifth album and they have fans that are going to be, “Oh this isn’t as good as the last one.” And if it hadn’t have gone well, I would have re-recorded over my shows.
Paste: Knowing that informs my feelings about it. One of the things I liked about the album was the looseness that it had. It sounded like you were having as much fun as the audience. It sounded like you were enjoying the jokes as much as you were enjoying telling them.
Gondelman: I had a good time. Hopefully the other people in the room had a good time. Otherwise that does not speak well to my acumen as a comedian. It was a nice night. It’s nice to get to do. It’s still a thrill and a pleasure that people come out to see me do comedy regardless of whether I’m here to support a recording or just when I’m doing dates inside or outside the city. I definitely try to project pleasantness on stage and I don’t have an especially aggressive set. I feel like the material was there and was worked over. I hope it came off as material that is professional but definitely there were a couple of moments where I might have booted a word. It was, like, “Well people get that. That happens to humans. I don’t need to do another show because I mispronounced the word ‘euphemism’ slightly.”
Paste: Let’s talk about some of your other work. Is @seinfeldtoday the thing that you’re most known for?
Gondelman: I think for a time it certainly was. It was the first thing I ever did where people thought, “Oh, he’s the guy from that.” Which was really nice to have. Even though in the grand scheme of things, a parody Twitter account isn’t what I would want to topline my obituary. I stand behind it as a fun thing to do and work on with my friend Jack Moore. It was a very exciting thing to have something that I helped create and helped write that people would go, “Oh neat. You did that thing!” Now, I think people associate me more with writing for Last Week Tonight or that’s a thing that I would say about myself first if people wanted to know what my professional resume was about.
Paste: Did that also help kick a few doors open for you, for other work?
Gondelman: Definitely. It’s nice to be associated with something people like. There are a lot of really strong comedians that are more talented and more prolific than I am, but it has helped me to be associated with something that people know and like. There’s so much good stand-up and it’s hard to get people to rise above the noise. It was just a stroke of weird luck that this thing that I was involved in became significantly bigger than me and dragged me along forward with it.
Paste: What about your book, You Blew It? What can you tell us about that?
Gondelman: I co-authored it with my friend Joe Berkowitz. It’s basically just about how the world is an unceasing nightmare and every interaction is a minefield for discomfort. You are a champion for attempting to do it at all even though anything could go wrong at any moment. And certainly will. Repeatedly. Which I think is slightly more pessimistic than my actual worldview. But we tried to make it funny. Here are the ways things are going to go badly but you can still have a very good life aside from that.
Paste: How did you guys land on this idea?
Gondelman: What originally happened was that Joe and I were pitching a fake pickup artist’s guide called Getting It Wet: The Nice Guys’ Guide To Tricking Women From Friend Zone To Bone Zone. We were really psyched about this project and wrote this whole proposal. Our agent went out with it and heard from publishers who said, “This is very funny and we absolutely won’t publish it.” We found an editor who really believed in us and we bounced ideas back and forth until we found one that would be less totally objectionable to readers of books. To me, the original idea didn’t seem beyond the pale, but I think part of that is I come from the stand-up world where you can say whatever you want and if people don’t like it, then you’re like, “Well, I’d better stop saying this.” That didn’t seem significantly dirtier than other things I say professionally all the time. It was interesting to adjust my sense of what I think is funny and what people will want to pay money to read on ground up trees flattened into pages and bound together. That changes things. I wish more books were funnier and dirtier. Why is it okay to write a work of literary fiction where horrible, explicit things happen where you can’t write a book of humor where silly, explicit things happening?
Paste: How did you wind up writing for Last Week Tonight? Did you have to go through an audition process?
Gondelman: I was a given the packet to audition from a couple different sources. It was a packet of sample material and then the next round where you get asked to write additional sample materials in a shorter time frame. For my first year there I was hired to do all the digital stuff for the show. Then after Season One, I got moved to start writing more for the show itself.
Paste: What is the process of putting a show like that together? Is it just from week-to-week you’re handed this big subject that John decides he wants to tackle and you get as an assignment, or are you pitching things?
Gondelman: It’s a combination of things. There are things that come from John or that come from our executive producer Tim [Carvell]. Some of those things they will have talked about amongst themselves or with the producers and researchers to make sure there’s a story worth assigning and they assign to us. Or we will pitch stuff and have that assigned back to us. It can happen a number of different ways.
Paste: Are there things that you pitched that made it to air that you’re particularly proud of?
Gondelman: Oh man. [laughs] There’s so much that has so many hands on it, that so many people punch up and enhance. But my favorite things that I’ve pitched are the really silly ones. And one that I think I can take credit for, because I don’t know that anyone else would want credit…there’s an app that I think is about to launch, that was announced last year called Peeple. We did a little bit on it that was written by Dan Gurewitch, and there’s a website attached to it called screamintothevoid.com. It’s a website where you type in something and you click “Scream” and it makes a scream sound and sucks whatever terrible opinion or thought you have into a black hole. So this story was pitched but in addition to that…for whatever reason they decided it was fun enough to make…I pitched a different app called Peeble where you submit a photo of yourself and you’re rated on a scale of 1 to 5 by actor/director/producer Mario Van Peebles. And Mario Van Peebles agreed to be in the piece so it was this very silly minute long thing of Mario Van Peebles assigning rankings to pictures of people on staff and dogs. It was really, really silly. There are lots of things that I’m really proud to have worked on but I’m just delighted that I got to pitch that very silly thing that got made.
Robert Ham is a Portland-based freelance writer and regular contributor toPaste. You can find more of his writing here;.