After being away from the stage for more than a year, Josh Gondelman is feeling very fortunate about the creative opportunities he’s had in comedy since coming back online. Or rather, you could say he’s been pretty pleased with the results following the return.
One such result comes in the form of People Pleaser, Gondelman’s first one-hour stand-up special. It’s had a bit of time to marinate with the masses since it’s release in June, but come to think of it, Gondelman himself had a bit of extended time to stew about it before it’s release anyway, having the recording date and premiere separated by 53 weeks, and it still seems to be making an impression on both the Stoneham native and his audience.
“With all of the lead-up to this special, there was a lot of thinking about I could’ve done this thing or that thing differently, or I wish I hadn’t fumbled over a certain word, but now it’s out in the world, and I’m sure there complaints about it, but everyone who has reached out about it has been lovely,” Gondelman tells Vanyaland. “I think it’s nice to be reminded that no other person lives in my head and is watching it through the filter of my own fears and regrets. I’m proud of it, but it’s nice to hear from people who don’t see me pushing up my glasses 15 times.”
Having already released a trio of albums over the course of his career, the stand-up vet is no stranger to putting his voice on record, and it shows in his confidence in being able to captivate audiences all over the country. But having to put together a set for your first hour-long visual special in roughly one whole month after having more than a year away from a live setting due to the pandemic, there was admittedly a bit of nervousness about what people might be sick of hearing at this point, since Gondelman pulled some chunks of material out of the catalog of yesteryear.
But to his delight, it all worked out as he meshed both the older material and the new material in a way that still felt fresh for both him and the audience. And at the end of the day, Gondelman aimed to put together what he felt would make the best special possible, and it turned out to be even more of a blessing in disguise than he had initially thought, as he was able to dust off some golden oldies and give them more space to breathe.
“Because this came up kind of quickly for me as I was in the middle of putting together a new set, it was kind of an opportunity to use some bits I had recorded elsewhere, but never on TV or a platform this big,” says Gondelman. “So rather than introducing myself with a mission statement, I wanted to use stories from older material that really illustrate who I am, and where I’m coming from. Otherwise, if I had done the special now, I probably would’ve given a snapshot of where I am now, but given the circumstances of how and when it came about, I was able to introduce myself with a bit more backstory, which is exciting.”
Everything about the special was thought out with a lot of intention behind it. Of course, the material was sculpted and polished to create a solid piece of work, but it was also the aesthetic with which Gondelman carries himself was also thought of to not only be strategically comforting and warm, but also another way to introduce himself in a visual way that further represented his almost legendarily sunny disposition and attitude.
“I always joke that sometimes, you see someone do a comedy special who must’ve said to themselves ‘now it’s time to dress like I’ve never dressed before,’ and then you find yourself wondering how they found leather pants,” says Gondelman. “So I really thought about that aspect, and it came from advice I had gotten from Gary Gulman, who is the greatest, when I had done my first late night set. He said that if I have a little money to spend to make myself look and feel comfortable, that’s important because it’s a visual medium, and it really translates.”
Having the advice of The Gul still in his ear after all these years, Gondelman also didn’t want anything he wore to come across as costume-esque, so he took his usual drip — a cardigan, corduroys, and a button-down shirt – and cranked them all up a notch, with the thought process surrounding how he would dress if he were meeting one of his wife’s relatives for the first time.
Another aspect of his outfit, and possibly the most unique to his wardrobe, was the sneakers he decided to wear for the occasion. When he isn’t fending off comedic barbs from people like Ken Reid and Patton Oswalt about a fictional cocaine habit, Gondelman was commemorating every show day during his run as a writer for the recently dissolved smash hit Desus & Mero with a fresh pair of kicks. Some were elaborate and loud, like his Dunkin’ Donuts sneaks, and some were more subtle and more common, but whatever the personality of the shoe was, the selection became an anticipated aspect of Gondelman’s social media presence week after week.
And even though he is a huge fan of fashion and the value that good sneakers add to an outfit, he didn’t want to make too much of a statement to any full-fledged sneaker heads that may be watching by wearing something as legendary as black and red Jordan 1s or the off-white Nikes that might distract viewers on account of the brightness.
What wound up bring the final choice are almost welcoming, right in line with that bubbly demeanor of his, and now he has “show day shoes” of his own to keep in the vault for the sake of a milestone memory.
“With the sneakers, the color pallet went from the ground up, where I found these Club 58 Nike SB Dunks that visually popped in a way that wasn’t comical or ostentatious, but they were still bright and fun,” says Gondelman. “Then going with the brown corduroys that I already owned, the navy blue Todd Snyder cardigan, and the Chambray shirt from Rag & Bone, I was shopping in places I normally wouldn’t, but I wanted to do it for the show and sort of look like the premium version of myself.”
As you may have guessed, being able to introduce himself effectively means a lot to Gondelman, and when it came to how the special would be marketed, that was also a very concerted effort to keep it as accurate and as representative of the energy he brings to the stage as possible. And so what if something like the title is shared with another special? As it turns out, that scenario, as he came to know of after the fact, made for an entirely new layer to be added to the humor and unique quality behind the whole thing.
“Oddly enough, after the special had been announced, I found out that Daniel Tosh also has a special called People Pleaser, but with him, it’s a little rye because he’s got an edge to him and a bit of a combativeness with the audience, so it’s very funny to me that we have specials with the name, yet they have very different presence.”
After 18 years in the comedy game, Gondelman finally has his first full hour special, and while it may seem like a lot of time to wait, the amount of stocked up material made for a potent final product that fully represents who he is and what has made him so loved and adored in the comedy sector. Gondelman just wants to make people laugh and feel good, and he really did try to make it cohesive and enjoyable while also putting forth a sort of Mr. Rogers-sequel comfortability, and he’s very happy that his objective came across.
“Having a wealth of time in comedy to draw on really showcases stuff from different albums, as well as a lot of new stuff, and so it really is a body of work in a nice way,” says Gondelman. “It’s a lot of my favorite stuff that I’ve performed in the past, but there’s also a lot of material that feels very present still, and shows where I am right now. I’m just really proud of how that all fits together and how it all integrated in a first special. Now the second one can show what I had been working on over the past couple years up to that point, but I’m glad I get to use this one as a way to introduce myself to people in that way.”