Stream It Or Skip It: ‘Josh Gondelman: People Pleaser’ On VOD, An Hour From The Comedian Who Offers Late-Night Pep Talks On Twitter

Comedians describe other comedians as nice usually to avoid calling them unfunny. But Josh Gondelman, considered one of the nicest guys in comedy by his peers, proves that nice guys don’t have to finish last in show business. Gondelman recorded his debut stand-up special last June at the Tribeca Film Festival, and it’s out this June via Comedy Dynamics for rent or purchase on a platform near you.

JOSH GONDELMAN: PEOPLE PLEASER: STREAM IT OR SKIP IT?

The Gist: Gondelman, a Millennial from the Boston suburbs, first gained notice online as the co-author of the parody Twitter account, @SeinfeldToday, imagining how the 1990s sitcom would’ve reacted to topical headlines of the early 2010s. After five years as one of the original writer/producers for Last Week Tonight with John Oliver, Gondelman jumped to become the head writer and an executive producer for Desus and Mero. You may have seen him perform stand-up on Conan, Late Night with Seth Meyers, or The Late Late Show with James Corden, but this is his first hour special.
In the hour, Gondelman jokes about coming to terms with his looks, his personality, and his relationship with his wife.
What Comedy Specials Will It Remind You Of?: If you Google nicest guys in comedy, the only other name that pops up as often as Gondelman is Nate Bargatze.
Memorable Jokes: Gondelman devotes the biggest set pieces in the hour to his wife, specifically two memorable moments in their relationship.
The first: On the day of his grandmother’s funeral, when a Sublime song made him realize that his girlfriend should be his wife.

The second: A closing story about their unconventional wedding, which banned any toasts from the family, maid of honor or best man, but did include a very memorable reception afterward.
Our Take: As an Emmy and WGA-winning TV talk-show writer, you might expect Gondelman to have a mastery on wordplay, which he demonstrated in the opening minute with a joke about the festival and the neighborhood of his taping: “Tribeca. It sounds like a couple of rich kids attempting to find someone to buy cocaine from.”
For serious comedy fans, this also taps into a massively lengthy inside joke among comedians on Twitter about Josh and his completely nonexistent cocaine addiction. He did cop to drinking more alcohol than before during the pandemic, but joked self-deprecatingly that even if he did have a dark side, “I’d be a monster, sure,” but not enough of one to warrant his own Wikipedia page (note: Gondelman already has a Wikipedia page, but without any red flags on it, so to speak).
Because that’s not who Gondelman is. He’s the guy who writes for late-night TV, and in his own late-night reality, is more likely than not to offer anyone and everyone their very own pep talk over Twitter. Of course, watching this hour of stand-up, I’ve also come to realize that Gondelman himself might not find this activity all that healthy, in comparison to his wife’s comprehensive book-reading on the other side of the bed.
Nevertheless, for a guy who began balding at 19, he has embraced his “dad bod” even without being a dad yet himself, and he’s well on his way to having the confidence of his 97-year-old great aunt.
And who knows? Perhaps some day, Jason Derulo will even write a song with his name in it.

Our Call: STREAM IT. Because you cannot help but feel at least a tiny bit happier about yourself and your life after spending an hour listening to him.

Sean L. McCarthy works the comedy beat for his own digital newspaper, The Comic’s Comic; before that, for actual newspapers. Based in NYC but will travel anywhere for the scoop: Ice cream or news. He also tweets @thecomicscomic and podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.

Where to watch Josh Gondelman: People Pleaser