Children, I’m not kidding: We used to pay one dime for each text message, similar to a telegraph.
Pretending to be a 19th-century pioneer in a pixelated covered wagon driven by oxen was our first computer game in kindergarten. We were instructed to travel to Oregon. The computer would inform us that one by one, our pals had passed away from typhoid, dystenary, or diphtheria. Our raft eventually splintered against rocks and we drowned in a river.
Netflix blew up when it came in the mail, one movie at a time. Our thoughts.
In 2025, being an 80s baby means having traits similar to the Grandpa Simpson meme.
Josh Gondelman, a 40-year-old fellow millennial, is also interested in discussing it.
At the turn of the century, we reached adulthood. “Turn of the century” is such a corny way to describe 1999, when Limp Bizkit rose to prominence, the Stoneham native tells me in an interview from his home in New York.
Gondelman’s new comedy show, Positive Reinforcement, will be available on Blonde Medicines’ YouTube page on June 27 at 8 p.m. and centers on aging millennials. The whole video can be viewed at the conclusion of this interview. (While you’re making popcorn, I’ll stop here.)
On July 11, the audio album, which includes bonus content, will be available everywhere comedic audio is sold or streamed.
He will also be speaking with his wife, author Maris Kreizman, about her new essay collection, I Want to Burn This Place Down, on July 2 at the Harvard Book Store.Yes, her husband is the subject of some of the pieces. He hasn’t yet read them, no. (This might get intriguing. Bring extra popcorn.
The former student of Stoneham High School (2003) and Brandeis (2007) contributed to the Emmy-winning shows The Marvelous Mrs. Maisel and Last Week Tonight with John Oliver on HBO. He used to be the executive producer and lead writer of Desus & Mero on Showtime. He frequently participates in panels on NPR’sAs astounding as Wait Wait Don’t Tell Me is, in my opinion, co-founder of the now-defunct Modern Seinfeld Twitter account. (Jerry, it was pure gold.)
The four-time Emmy winner is known as the sweetest guy in comedy and got his start as a stand-up comedian in Boston: (Homepage of the website: comedian, author, friend.)
I gave Gondelman a call, and he was incredibly kind before his big week for a comprehensive interview. I’m envious of his Dunkin sneaker collection, and we discussed Seinfeld, MapQuest, Y2K, John Oliver, Good Will Hunting, and more.
Gondelman, Josh:My first reaction upon returning to live performance after the pandemic was, “Oh.” Now, I’m one of the elder guys. The intellectual and philosophical grace of embracing change and new things when they’re excellent is a key element of aging gracefully. However, it’s nice to know that I don’t have to state that cryptocurrency is new.
There was a young woman in the front row when I was performing in the college town of Bloomington, Indiana. I could see something in her face when I made a Y2K joke. “Does the term “Y2K” mean anything to you?” I asked. “No,” she said. Then I had to explain Y2K: No one believed that a year would ever have 000 in it, so we assumed that all of the missiles in the world would fire and that all of the computers would fail. Then, it took an incredible amount of work to ensure it didn’t occur. It sounds absurd.
Indeed! We are the final generation to have had [offline] experience, according to what I’ve read. When I was younger, I had to consult my parents’ collection of World Book Encyclopedias from the 1960s if I needed to learn something new.
It’s fascinating: we believed that the internet would democratize education and address the issue of misinformation, but now we’re in the complete opposite situation, with people using ChatGPT as a search engine to obtain completely false information that has never been true, rather than out-of-date information.
Absolutely! I recall that this was short-lived during the laserdisc period, when it was like [sounds like Homer Simpson]. Movies are large CDs, and music is CDs.
Absolutely! Recently, I was discussing with a friend what the last technology was that was essentially good with few disadvantages. Instead of using your phone, I developed the GPS unit for your vehicle.
Of course. We didn’t have to complete NFTs, but I’m really happy we did that. Growing up, in my opinion, is about remaining skeptical while accepting new things with an open mind. Just because something is new doesn’t mean we have to like it.
Every year, Stoneham High held a large variety show. Each grade’s class officials would compose a skit for their grade to perform. I was the class vice president my freshman year. I’m not sure why I ran; perhaps I just wanted to be involved. Based on comic writing, I easily won the title of Class President for three years after our sketch became popular.
At the now-defunct Beantown Comedy Vault of Dick Doherty. Improv Boston and the Comedy Studio were my home clubs. Boston was an excellent starting point because it offers a wide variety of shows, including fundraisers in Italian restaurants, a large comedy club in Boston city, and a hip independent room in Cambridge. I was rather grateful for that cross-training.
When the show debuted in 2014, I began working there. I began writing for them on social media and online. My foot in the door was that. I was promoted to staff writer after the first season. Tim Carvell is an excellent executive producer; John is fantastic. What a unique pair they are. There, I gained a lot of knowledge.
Anyone can [pitch a tale] on the show. Oh, I read a story, let’s investigate. This would captivate John and Tim. Echoing a media narrative was not our goal. Is there anything we can add? was the question. Is there a prevalent misunderstanding we can discuss?
It had to be something John felt compelled to talk about in the first-person with his face and name attached. That was the obstacle to overcome. I gained a lot of knowledge about writing jokes. They take great care to ensure that the jokes enhance rather than detract from the plot.
I d been doing a lot of stand-up, occasionally someone would give me an opportunity to apply for a late night show. Then I had this viral social media success my friend Jaclyn Moore and I had a parody Twitter account.
Indeed!
Oh, thank you. It was so silly, and it got a lot of attention, and pushed me into a position where I was able to get my foot in the door more places. I got some freelance work writing jokes forBilly on the Streetwith Billy Eichner.
It was so great, and really buoyed my spirits. Then six months later, I got Last Week Tonight.
Last Week was a wonderful job with wonderful people, and a lot of staring right into the mouth of hell.
Extremely heavy. We did one on the opioid epidemic, and there s so little that s funny at all. You have to write jokes about the saddest things that have ever happened in the world, and figure out how to do that with grace. It s delicate work. I thought: if I ever want to do any different kind of comedy writing, I should keep my ear to the ground.
At Desus & Mero I developed different kinds of muscles. It was wonderful. I was there for four seasons, and then was a stand-up consultant on the final season ofThe Marvelous Mrs. Maisel.
My friend Dan always said and it s true If they had cell phones, you would lose half the episodes. I thought: But think about all the episodes you d gain. Because it s not just We can t find each other in this movie theater it s the etiquette of using this technology.
When the WiFi George usually steals suddenly has a password, he becomes addicted to trying to hack in. J: Just get your own! G: NEVER!
I tweeted a couple from my own account. My friend Jaclyn was like, This could be something. We started @Seinfeldtoday we were both plugged in on comedy Twitter and media Twitter. It blew up overnight. We stopped doing it [in 2015] when we got too busy, but it was a great calling card. It opened a bunch of doors.
One was something like: Jerry had to break up with his girlfriend because her phone automatically connected to Newman s Wi-Fi.
One of the earliest ones was like: Elaine s neighbor makes his WiFi password an insult about her after they break up so the whole building will see it.
Totally. It was one of the first things I got into where I thought: Oh, this is what the grown-up world is like. Obviously, it s not really but in some ways it kind of is. I grew up with this warped sense of how much scheming and machination is required to be an adult, just because of how much George Costanza informed my lens on the world.
Same. It was huge for me. My wife was under-the-weather a couple months ago and I said, Why don t we just throw on something familiar. She gave this little cough and said weakly, Put on Fusilli Jerry.
OK, so I have several pairs of Dunkin-adjacent sneakers. The ones you re talking about were theircollab with Sauconyfor the Boston Marathon. I don t wear them much because I could never replace them.
I also have a pair of New Balances that have Dunkin colors not an authorized collaboration, just coffee brown with the pink and orangeon the N.And I have a pair ofAir Max 90s in Dunkin colors. They went on sale, and I was like, I m gonna get a second pair for when I run through the first.
Only once. I was opening for John Oliver at The Wilbur in 2014. I said to the crowd, It s very meaningful for me to be here with you. This will always feel like home. I get a nice round of applause. Then I said, That said, Ididmove to New York City three years ago because I wanted to be happy and successful.
I got booed and booed. I said, No. You aren t allowed to boo. You could also leave if you wanted those things. Good Will Hunting isn t science-fiction. And I got booed and booed. I did my next bit, got a little applause, and said, No. You already decided you were against me. I don t want your applause.
This is an extremely 2014 sentence: we met at a party Maris was throwing to celebrate the five-year anniversary of her successful Tumblr blog.
Watchthe full Gondelman special here, starting 8 p.m. June 27.
Lauren Daley is a longtime culture journalist. As a regular contributor to Boston.com, she interviews A-list musicians, actors, authors and other major artists.
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