I love comedy. I love people who do comedy. And most importantly I love funny people. A few months back, I somehow stumbled across an amazing Twitter handle called @SeinfeldToday (as you may or may not know, I love Seinfeld), anyway this twitter account posts funny adventures as if the cast of Seinfeld was still on the air and it has 848K followers. What’s that all about? The premises in the tweets involve things like online dating, direct messaging and using the wretched term BAE. Honestly, babe isn’t that much harder to say. I then clicked on @joshgondelman as he is one of the writers of the account. So, Josh not only writes this account, but he’s also a successful standup comedian with regular shows at the biggest comedy clubs in New York and LA, he has a book coming out in the fall called Your Blew It, and he is a writer for Last Week Tonight with John Oliver. Last Week Tonight with John Oliver. Probably one of the funniest news shows ever made. For those who don’t watch it, please start immediately. It will get help you get up to speed with the idiocy that goes on in this world.
Anyway, I reached out to Josh to see if he would be interested in an interview and he said yes. I couldn’t believe it! With his schedule I honestly have no idea how he has the time to even eat. And, last week, on Friday, he sent me his answers. Here they are for your reading pleasure:
JTTM: So, you’re a writer for Last Week Tonight with John Oliver, you’re writing a book, your standup calendar is full – I checked it on your events page – and you manage at least two very successful twitter handles, your own @joshgondelman and @SeinfeldToday. Now, if I do some simple math based off of all this, it seems like you’re writing and joking every minute of every day. Are you ever not writing or do you even write in your sleep?
JG: I do spend a lot of time writing and performing. I’m trying to cut back and live more of a life. My girlfriend and are in the process of acquiring a dog, so I’m hoping to spend more time outside of work hanging out at home doing fun and domestic things. Or going outside and having fun there. Especially since the process of sleep-writing jokes leads mostly to nonsense.
JTTM: What’s your favourite part of getting on stage?
JG: For sure my favorite thing about doing standup is getting to tinker with a new idea. There’s a really exciting period between when a joke starts to work and when it feels like a bit that you can rely on in your act. I wonder if that’s unique to standup though. I bet if a scientist were working on a time machine, he or she would feel like the best part was the first time it worked and they traveled through time. Not the middle part where they just interact with time in the regular way.
JTTM: What was the best/worst heckle you ever received? Did you fire back a rebuttal, or did you just appreciate the well-timed insult?
JG: By far the worst heckle I ever got was when I was offstage. I was walking to the back of the room after bringing up the second comic on a show I was hosting, and a woman turned to her friend, pointed to the other guy and said (not even knowing I was around): “Well at least that guy is good looking.” Outside of that, one time a college student raised his hand during a gig to ask if I knew Kevin Hart.
JTTM: How did you and @JackPMoore decide to do Modern Seinfeld aka @SeinfeldToday? I know when I found it I thought it was genius. I often have thoughts about how something’s in my life would be amazing in a Seinfeld episode and what would George say about it.
JG: Thanks for the kind words! I had just started tweeting plotlines from my own account as a goof, and Jack had the sense that this could be a real thing, so he snapped up the Twitter handle and we started working on it together. My friend (comedian) Dan Boulger had once said that half of the Seinfeld episodes would be done for if they had cell phones, and that always stuck in my head, which I think is why I started tweeting what those shows would have been like.
JTTM: What’s the best thing about it? Your 140 characters of Seinfeld situations.
JG: Definitely it’s not having the pressure to write an entire sitcom. It’s WAY easier to write two sentences. If you can get work doing that, I recommend it.
JTTM: How’d you get your chance to work on mainstream television (HBO)? So many aspiring writers and comedians are wondering (mostly just me).
JG: A lot of failure and then less of it! I did standup for a long time and then started doing a lot of freelance writing for mostly women’s magazines, and it was just work and work and work and eventually people started asking me to submit to things.
JTTM: Did you always know you wanted a life in comedy?
JG: I don’t know if I always thought I’d do it professionally, but I’ve always loved jokes. My parents have a VHS of me telling a joke at like age 3 and getting distracted by an ant walking by. So it’s always been an interest of mine.
JTTM: Your soon to be released book You Blew It is coming out in October, can you describe it a bit? Example: don’t read if you have heart problems because you may have a laugh attack, or it’s a book about failing your way to the top. Or, just anything about the book that you want to share.
JG: Ha! It’s kind of a book about how life is a nightmare even under the best of circumstances, and it’s a guide to how you can lean into that and either drive your life into the ground or acknowledge that we’re all (even when things are great) subject to the general hassles of society.
JTTM: How was the co-writing experience with Joe Berkowitz? Do you ever have funny off’s where you compete for who is the funniest?
JG: It was great! Joe is really funny and hardworking, and it was nice to have someone to set the pace in terms of, “Oh, my stuff I’m turning in has to be good because his is.” So it wasn’t competitive. More inspirational than anything.
JTTM: What were the most challenging and the most exciting thing about writing your book?
JG: The most exciting thing was making a tangible thing with my name on it. That happens so rarely in comedy. It’s like, articles in a magazine or standup sets or tweets or tv jokes are the things I produce most of the time, but it’s really gratifying to have a physical object that says I did it. I accomplished something. ARE YOU HAPPY, STONEHAM HIGH SCHOOL CLASS OF 2003? (Just kidding. I really like the people I went to high school with.)
JTTM: Who are your favourite comedians?
JG: Oh gosh. This question always ends with me listing everyone I’ve ever met, so I have to give myself some scope. This week I got to open for Emily Heller’s CD recording, and Wyatt Cenac was on that show as well, and it’s always a joy to watch the both of them. Plus Aparna Nancherla recorded an album in the same room the night before, and she’s amazing. And Gary Gulman did a set on Conan that was so good it made me feel like I don’t even know how to do comedy. But the real list is like a thousand people long. I can’t get into it.
JTTM: Is being in a Writer’s Room as amazing and as stinky as I think it is?
JG: It’s great! I like the chance to collaborate because standup sometimes makes you a lone wolf!
JTTM: Grammar check, is it a Writers Room because there are lots of writers in it, or is it a Writer’s Room because it’s their room?
JG: It could also be “Writers’ Room.” The options are limitless!
JTTM: Do you ever do your standup tour in Canada? Toronto is a lot like New York, but less busy, less cool, and with less angry people.
JG: I’m coming to Toronto in July! The 2nd through the 4th I’ll be at Comedy Bar. It’s my first time visiting the city, and I’m very excited!
JTTM: Do you have a writing play-list? Certain artists that get the jokes flowing?
JG: I don’t usually listen to music when I write, but I do have a bookmark on my web browser for M.O.P.’s “Ante Up” remix for when I need to get psyched up to work on something.
JTTM: Is there anything else on the horizon we should keep an eye out for?
JG: Oh dear. You’re really making me feel like a failure. I guess, no. There’s nothing other than the things we’ve mentioned. Wow. That’s pretty bleak. Well, wait! My girlfriend’s book, which comes out on the same day as mine.Slaughterhouse 90210 the Book by Maris Kreizman! And also pictures of our new pug on Instagram!
JTTM: Lastly, what are you social handles so that my readers can digitally follow your every move:
As you can see he’s a cool dude with a career on the rise, so try to see his show now while it’s still affordable because it won’t be for much longer!