Josh Gondelman: American Sweetie Pie
The comedian and Emmy-award winning television writer on authenticity, touring with John Oliver, and why Boston gets a bad rap.
VANCOUVER – I’m coughing as I sit at the desk and open my 2015 MacBook Pro to call New York City. It’s just after 7 a.m. and while it’s been a beautiful few weeks on the South Coast, I have been too sick to enjoy it. I spent the previous Saturday (the last nice Saturday of the entire summer!!) swaddled on the couch in my striped Ralph Lauren pajamas, dozing in and out as Seinfeld played in the background. Last night was Kevin’s 32nd birthday. I felt well enough to attend but still spent the night coughing into my shirt. Now Leah has a cough. She’s trying to blame me – but without a proper diagnostic panel, her guess is as good as mine.
You can’t infect someone over FaceTime so I dial Josh Gondelman for our interview. It rings a half dozen times before someone answers. I can’t see their face but the top of their head tells me I’ve got the wrong number. A thin flash of black hair sits like roadkill against an eggshell white wall. Before I can say anything the guy disconnects. I check the number again and re-dial. It only rings twice before I see America’s Sweetie Pie staring back at me.
A well-established comedian and writer, Josh has carved a niche for himself by combining an old-school standup style with his own unflinching sincerity. Our conversation, which has been edited and condensed for clarity and which I spent an annoying amount of time coughing through, touched on his recent tour dates with John Oliver, his time writing for Last Week Tonight, growing up in Boston, Hasan Minhaj’s pursuit of “emotional truth,” Josh’s favourite seltzers, adopting elderly pets, and joking around with former Presidential candidate Hillary Rodham Clinton.
It’s worth noting that a few hours after our interview Josh and other members of the WGA’s leadership team announced an agreement had been reached an agreement with the Hollywood studios. Who says silly goofy guys can’t achieve serious results?
ES: Hello!
JG: How’s it going?
ES: Good. I just FaceTimed the wrong number and the person actually answered which has never happened before.
JG: This could be the start of a really exciting adventure.
ES: All I could see was the top of their head and I was like “That doesn’t look like the top of Josh’s head.” Hmmmmm.
JG: I have a very distinctive top-of-head.
ES: They hung up without saying anything. I was like “Let me check my facts here.”
JG: That’s so funny.
ES: Why would you answer? I don’t understand! Anyway, other than that I’m good. How are you?
JG: I’m okay thanks. It’s really rainy here this weekend so I feel a little cooped up, but other than that not bad.
ES: You’re in New York at the moment?
JG: Mhm.
ES: I was longingly talking about autumn in New York yesterday and my fiancee was like “We should check the weather there.” And it was the exact same as Vancouver. It completely killed the fantasy.
JG: It was beautiful for two days and then it just started pouring.
ES: Did I see a video of your pug in a rain jacket?
JG: I posted a photo of her. She’s very cute in her fall fashions.
ES: The pug seems a little old. How old is she?
JG: She’s sixteen.
ES: Oh my god. Have you had her since she was a puppy?
JG: No, we adopted her about eight years ago.
ES: So she was eight? That’s still pretty old.
JG: They called her a senior pug even at that age.
ES: And sorry what’s her name?
JG: Bizzy. When we adopted her she had the same name as one of our human family members so we changed it to that.
ES: Is that a reference to anything?
JG: It’s a hodgepodge of stuff but nothing specific. She does beatbox like Biz Markie when she gets stressed out, which I think about a lot.
ES: We adopted a senior cat. He’s named Studio or Stu for short because they found him in a film studio parking lot. We thought it was cool. We never changed it.
JG: S-T-U?
ES: Yes. But then my grandpa is also named Stu so people wound up thinking it was an homage to him.
JG: Two Stu’s.
ES: I’m guessing you’ve been out in the rain with Bizzy already this morning?
JG: My wife generously offered to take her out this morning because I took her out for night walks yesterday.
ES: Night walks are a different beast. We’ve had to do that when we take care of our friend’s dog before. I feel like nobody ever really wants to do it.
JG: I know. We have a pretty good system where I’ll come home from doing standup and Bizzy will be waiting to go to bed and I’ll take her out before I turn in. That’s not bad because I’ll be in the rhythm of things already. I already have my shoes on. It’s different when you’re on the couch and ready to go to bed and then remember you have to take the dog out.
ES: You’re watching Frasier and suddenly it’s like “Oh shit I forgot about this again.”
How often are you doing standup at the moment? From my limited perspective, it seems like you’re the busiest man in show business.
JG: I’m out a lot. I’ve been on the road most weekends through the spring and summer. I’m out several nights a week in New York, depending on how assiduous I am about booking emails.
ES: You just got off tour with John Oliver?
JG: Yeah – I did a couple of dates with him. Two theatres, one in Hartford and one in Philly, and I’m going back out with him this coming weekend while his normal opener, Brooks Wheelan, is out in Alaska touring there and filming a special.
ES: How were those shows for you?
JG: It was great. John has really fun crowds and it’s great to perform in a big theatre and not worry about how many people are there to see me. It’s just showing up and doing the job. It’s a fun way to get to do it. So much about comedy and writing and performing is increasingly about the business/marketing side. It’s nice to be brought on to just do the jokes.
ES: What is a John Oliver fan like?
JG: It’s a real smart crowd, generally, and pretty well-behaved. In Philly, it did get a little Philly, which I appreciate.
ES: Laughs.
JG: I say that affectionately because I feel the same way about Boston, where I’m from. I started doing stand-up in Boston and I think the two crowds are very similar. They want to fight you. Ultimately, they want you to win. But they are going to fight you.
ES: Do you feel like growing up in Boston has made you an expert in hecklers?
JG: Not necessarily when it comes to heckling, but I do feel more equipped than you’d guess to deal with chaos and chaotic energy in a show or in the theatre. It’s so funny to have a couple of people chiming in in a 3500-person theatre. I feel at ease with that. I obviously prefer people to be paying attention, but starting in Boston and performing at fundraisers in Elks Lodges or Italian restaurants in the city gave me experience with every type of crowd and I think it expanded my pallet. My tool belt got a little fuller from those experiences.
ES: It doesn’t throw you off your game because you have a parallel to compare it to.
JG: Totally. I think there’s something really special about people who seek out specific circumstances, who go to where “their crowd” is, or who cultivate an audience for themselves so that they can create art that is uncompromising of their vision. I think there are special, wonderful results when people dedicate themselves to that. But I also have some townie pride in being able to go into a room and say “Whatever happens here I can do the job.”
ES: It’s almost like a trade person or Green Beret or something. Being able to parachute into any situation and get the job done.
JG: Yeah and I think a lot of stand-up is having to do that. So much of it takes place under slightly suboptimal conditions, even for people who are really thriving. You’re in comedy clubs with food and drink service while you perform, and you’re getting booked for colleges or corporate gigs that pay well but the audience didn’t know they were going to be an audience.
ES: Can you think of an instance where you felt things were suboptimal, as you put it?
JG: I did a show once where the guy booked it in a bar on the south shore of Boston. So, like, the suburbs. The Red Sox game was still on the TVs and there were no lights on the stage. I remember specifically that the guy who booked it kept making the show run long because he didn’t want to perform until his dad got there. He wanted his dad to watch his set. And then his dad showed up and only watched the Red Sox game. It was so bleak. It’s like Dennis Lehane wrote a novel about a comedian.
ES: Literally. What in the Arthur Miller did you get dropped into.
JG: Seriously. In 2013 I did two college gigs, one week apart. One was at this 700-person theatre on campus. It was an artsy-leaning public college in Missouri. And it was awesome. I thought “This is one of the best shows I’ve ever done.” I was on top of the world.
The next week I was performing at 11:45 AM in the open student centre of this other school in East Texas. There was no seating. There was a little stage. People were not there for entertainment. I think if the same group of students was in a theatre I would’ve had a chance. But there were 25 of them sitting there. I remember saying, “Oh are you here to watch the show?” And one guy was like “Nah man, this is just where they put the chairs today.”
ES: Laughs. Life comes at you pretty fast.
JG: Life comes at you pretty fast but the hour goes by pretty slow.
ES: It’s incredible that anyone sticks with stand-up. I know a lot of people do but it’s so hard to brush something like that off.
JG: One fascinating thing about it was that my college agent at the time booked the gig because she had a relationship with the talent booker at the school. I guess the last person she had booked was a little too dirty, a little difficult to work with. I think they were demanding or maybe talked trash about the school’s setup or something. So my job was truly just to go there, not talk about sex, not swear too much, and be easy and polite. I was contractually obligated to eat it for 45 minutes. I was off stage at 45 minutes and one second.
They were like “Hey! That was terrific. Thanks so much for coming out.”
Like, “You thought that was good?”
“Yup, that was exactly what we wanted.”
ES: That’s so interesting. You were basically a comedic diplomat.
JG: I was the charm offensive.
ES: Going back to Boston, it seems like a really great comedy town in terms of venues but also performers.
JG: I think the topography of the scene shifts over time. When I was coming up in 2004, the big club was The Comedy Connection. It was at Faneuil Hall, which is in the tourist area. It seated 450 people maybe, which is huge. Now the big club is Laugh Boston, which has been at the Seaport for I think 10 years now. But there were a couple of years with no big club. It really ebbs and flows. It’s been steadier for a while now, with some independent venues cropping up which rules.
As for performers, there are so many people. You can do every kind of room and work with people who do every kind of comedy. When I started Chris and Dave Walsh were doing real weird innovative stuff that I loved, but you can also work with someone like Tony Viveros who is just a master of standup and has been doing it for decades…
ES: How would you describe your comedy style? I know you’re very funny but do you consider yourself more of a classic comedian?
JG: I feel pretty traditional in terms of presentation definitely. I just did a podcast with Wil Anderson and I said that when people ask I describe my comedy as “friendly.” I’m not doing anything that breaks the form but what I try to do is be myself on stage, which is what makes it different. My style might be familiar to people but I think that approach lets me get away with having a specific energy or talking about things differently because the presentation is so comforting maybe.
ES: The word that comes to mind with you is sweetie-pie.
JG: Laughs.
ES: Everyone seems to have nothing but nice stuff to say about you. Even your newsletter is sweet. It’s just funny.
JG: I try to bring a gentle energy to things. That’s partially because it comes naturally to me. I don’t do aggression well. Not that I’m not incisive or have jokes that are hard but I think there’s a gentleness and I try to create a welcoming environment when I’m on stage. It’s fun to take that to places like Boston, Philly, or New York and to try to bend audience expectations to meet that.
ES: Are you sure you’re from Boston?
JG: Laughs. I think Boston is underrated. People talk a lot of trash about it. If you were only to go off public perception, you’d think you show up on a plane and then one of the Dropkick Murphys hits you in the back of the head with a pipe and then they Clockwork Orange you as a parade of hate crimes go by. Obviously, the city has major issues, as all cities do. But I think the good parts of it are a little more unsung.
ES: Full disclosure: for a not brief period of time I really wanted to move to Boston for whatever reason. I don’t know where I got this idea from. Maybe it was the Harvard connection or something. I thought it seemed very romantic. Laughs.
JG: Hell yeah! This is the time of year for it. You go to New England in the fall. There’s foliage and there’s students going back to school. The Red Sox are having the last gasp of their terrible season. There’s a nice buzz in September there.
ES: A nice sense of tradition. The Red Sox are losing, Dunkin’ is bringing in its fall harvest. Everything is as it should be.
Feel free not to answer this but what do you make of the whole Hasan Minhaj debacle and reports that some of the more personal parts of his act were essentially fabricated?
JG: Sure. It’s tough to wade into it because there’s so much at play there. I think everyone has their own line for how factual they want their material to be. That includes performers and audiences. It’s interesting to see where that lines up and where it doesn’t. I’ve been really interested in following that conversation because I’ve enjoyed Hasan’s work very much. It’s interesting to wrestle with and something I think about as a performer. What do I owe the audience in terms of literal factual truth and what can I massage for artistic purposes?
More generally, I also think it’s a matter of what you can get away with. I think if you watch Bo Burnham’s Inside, he’s portraying the feeling of isolation and loneliness. I think there are people who see it as a skillful, artistic rendering and there are people who don’t immediately realize he didn’t live in that one room and feel like he tricked them. So I think it’s an interesting gradient and worth having conversations about.
ES: I think it’s also interesting that we as a society put such a high premium on authenticity. To steal a line from Hasan Minaj, “the emotional truth” of Inside felt relatable to so many people because of COVID and the collective experience of the pandemic, and the toll it took on mental health. The problem, I think, is that when you don’t explicitly tell people that something is embellished or fantasy then they get confused.
JG: I think that’s the thing. Nobody is 100% authentic in a performance. But people want to feel like they’re watching something that has “authenticity.” In that sense, people are signing up to be tricked, but how far are they willing to go? Once the trick is exposed, how do they react? And that applies to people like me as well. This isn’t to defend all un-truth in comedy but it’s such an interesting gradient. You watch someone like Dave Attell whose act contains full-on surrealism, or even Dave Chappelle’s early work, which dabbles in magical realism. Nobody is mad because there’s a level at which bending the truth feels acceptable, depending on how it’s portrayed. But there are things that feel less like art to audiences and more like deceit, and it’s interesting to see what makes the hair stand up on people’s necks.
ES: I also wonder what you think given that Hasan is operating in proximity to The Daily Show, which is in proximity to journalism – though they obviously insist it’s only comedy. But at a time when media literacy has never been worse, I wonder if you think audiences lose sight of the distinction?
JG: Obviously he’s working in different mediums. The format show versus standup, where I do think you get different artistic license. But I wonder if people have a harder time accepting what he says as literal, factual truth when the statement of his artistic mission seems to be “emotional truth.” Regardless of how factually accurate the standup is, to do an artistic project with a stated aim of discussing high-stakes issues that raise feelings in people, rather than informing them, is a separate thing… I’m curious what his work will look like after this.
ES: You’ve written for John Oliver’s show Last Week Tonight. What were the conversations like among the staff when it came to the intersection of entertainment, journalism, and comedy?
JG: I always thought the endeavor was to do the funniest show that is also true. Or, the most accurate version of the story that is also funny. Those are two sides of the same coin and sometimes it would tip in one direction or the other, but my thought was always to make the show as funny as it could be without being inaccurate. There are people on staff whose job is to make it as accurate as possible without squeezing the humour out of it. That push and pull between comedy and accuracy was really interesting. Sometimes it’s funnier to lie, but sometimes it’s funnier to state something in a way that doesn’t make the point as accurately and strongly as it could be made… I think on that show there was a premium on doing the joke that is in service of the larger point. It was a really cool challenge to get to work on something where you’re walking that tightrope. The comedy writers want to make something funny while the research staff want it to be accurate and illuminating. Those are two compatible goals but you have to balance them. They don’t happen simply because everyone is working on them together.
ES: And it’s a formula that could result in failure if the two sides aren’t able to collaborate together.
JG: It was a super great staff on both sides of the office. The writers are really brilliant, really funny and the research staff are really sharp and really astute. John and Tim Carvell, who is one of the executive producers, would go over every script. They have a really clear vision of what they want for the show, which was helpful. To have their creative, comedic, and story-telling vision be the filter that everything is processed through.
ES: Were there any segments in the show that you remember being a tightrope walk between accuracy and entertainment?
JG: For the bigger stories, they really liked getting into the nuance of stuff and sometimes that meant you couldn’t take as big of a swing comedically. We did a very early story, pre-COVID, about vaccines and vaccine skepticism and wanting to go really hard at the idea of that being a harmful societal force, without being shame-y towards people because there are legitimate reasons to not believe in everything touted by the pharmaceutical industry, and the medical establishment does have blind spots. So not wanting to throw out the baby with the bathwater on that story was an interesting challenge.
But then there are stories like NASA sent a bunch of mice to space which are pretty silly and where you can take bigger swings because you have less of a premium on getting information into the minds of the viewers.
ES: One thing I appreciate about your comedy is that you’re not afraid to be silly.
JG: Oh, I love silliness. I think that, to me, comedy can do a lot in terms of bringing new ideas to people and opening people up to stuff they may not want to hear otherwise. But one of the ways I like to engage people is through being goofy, as opposed to being incredibly ardent on stage. There are people who communicate things with great urgency and a real powerhouse performance. That’s not what I bring to the table. I like working in a goofier way. Even when I worked for Last Week Tonight, I’d try to get the point across in the dumbest way possible. That was really fun for me because I think John has such trust with his audience. Such gravitas. He really takes his job as TV host seriously. I think he doesn’t want to betray the people who believe what he’s saying. It’s fun to couple that status with a dumb pun or silly graphic.
ES: Were you goofy with Hillary Rodham Clinton?
JG: So she was on the phone for NPR’s Wait, Wait Don’t Tell Me. But I’ve done episodes of that show with her, and with Malala, and I consider part of the job, in a comedy context, to be silly. As silly as you can get away with without insulting the dignity of who you’re talking to. Especially when there’s a gradient. Obviously, Secretary Clinton has a lot of political influence and social capital, but there’s still the gradient where, as a man, I didn’t want to say something gross or untoward. So I needed to figure out the comfort zone. Can I get her to be a little goofier? With Malala, the challenge was to create a space where it feels fun and enticing to goof around a bit. Like, why don’t you come play our game for a bit? I think the show provides a good context for that. People know they won’t be made to look stupid because they’re playing around.
ES: Do you feel like you got to that point with either of them where they were throwing the ball back to you?
JG: I thought Malala was super funny. She made a joke about being taller than Tom Cruise in heels at the Oscars. With Senator Clinton, I think it’s different when someone is a politician because it’s tougher to just play. You are a person who is in charge of things or has influence over things even if you aren’t in government. But she was really funny and sharp. At the start, you could tell she was doing the show to talk about the Clinton Global Initiative. She had her talking points. But once she felt like she had gotten that across, you could feel how present she was and how astute she was. How fast her brain works. And I think because she’s no longer an elected official she got to play around a little bit more than, say, a sitting senator.
ES: Were you always politically minded? Or did that come to you later, through working on stuff like Last Week Tonight?
JG: I’m certainly more informed having worked in that world. I’m constantly learning things and refining my point of view. I’d probably be embarrassed by what I believed 5 or 10 years ago but I think that’s part of growing up. I remember thinking I should have been more informed, but I also remember arguing with a Republican English teacher in high school about the U.S. invasion of Iraq. That kernel of awareness was there even if I wasn’t fully formed.
ES: It takes a while for ideas to percolate or solidify. You don’t have to have a perfect opinion on things immediately.
JG: Sure. And to not beat myself up for where I was. It’s not like I was doing a ton of harm. I just realized I could do more to be better informed, and more helpful. 21-year-old me wasn’t a member of Congress.
ES: If more senators were like you Josh, America might have a better chance. Laughs.
JG: I just want to be a well-intentioned comedy dumbass.
ES: To ask you a comedy dumbass question, when I interviewed our mutual pal Katie Heindl she mentioned she was a big bevhead. Are there any beverages you’re obsessed with at the moment?
JG: I wrote a little bit about Polar Seltzers for Slate over the summer and they sent me a big package of their seasonal flavours, which were hard to get in New York. They don’t distribute them as thoroughly as the regular flavours. So I’ve been working my way through those. That’s been pretty good.
ES: What’s their best seasonal?
JG: The Mango Limeade. I have one can left that I’ve been saving. When I finish it, it will feel like summer is over for real.
ES: Do those have alcohol in them?
JG: No they’re just sparkling water.
ES: Do you drink?
JG: I do. It’s not a sobriety thing. It’s more so I’m not drinking coffee and soda all the time.
ES: It’s interesting how much you can tell about someone based on what beverages they consume. It’s intimate knowledge. Mango Limeade tells me a lot about you.
JG: I know people in the seltzer world who go just plain. Water and bubbles.
ES: Ew.
JG: I mean, I like it but I do like the variety.
ES: That just seems so not fun, you know?
JG: But it feels like the seltzer equivalent of black coffee. No frills. Which I respect.
Josh Gondelman is a comedian and writer. He is proudly from Boston but lives in NYC.