Workspace 101: Comedian and Writer Josh Gondelman's Boston-Friendly Desk in the Heart of NYC

The "Desus & Mero" writer may own the only Marcus Smart jersey within a mile of MSG

April 1, 2020 6:00 am
“I haven’t decorated yet" -  Josh Gondelman
“I haven’t decorated yet" - Josh Gondelman
Daniel Shapiro for InsideHook

This Is Workspace 101, a series in which InsideHook goes into the studios, offices, garages and laboratories of the most creative people we know to understand just how much the space in which they work impacts the work itself.

“Nice Celtics jacket,” says Josh Gondelman as he leads me through Desus & Mero’s new office space in the New Yorker hotel, just three weeks before COVID-19 would shut down the show’s taping. This compliment takes me by surprise since I thought I was in Knicks territory —Madison Square Garden is across the street and, more importantly, both Desus and Mero are die-hard Knicks fans. But, then again, it’s coming from Gondelman, commonly known as the “nice guy” in comedy, even though he prefers the adjectives “polite” or “friendly.” (In comedy circles, calling someone “nice” can be code for “don’t book him.”)

Gondelman, a respected standup comedian and author of Nice Try: Stories of Best Intentions and Mixed Results, is co-executive producer and writer for the hit late night show, Desus & Mero, which migrated from Viceland to Showtime in 2018. Now in its second season at Showtime, the free flowing show has hosted guests as illustrious as David Letterman, Missy Elliot and John Mulaney.

A candy jar “will help you make friends” (Daniel Shapiro for InsideHook)

Gondelman leads me into the writers’ room, an open space with six wooden desks, stained dark, and a view of Madison Square Garden across 9th Ave. “I haven’t decorated yet,” Gondelman apologizes, explaining they only moved into this office space two months earlier. Indeed, a banker’s box rests at the foot of his desk with “Josh Gondelman” sharpied on the side. For the first Showtime season, Desus & Mero was housed in the same building as Last Week Tonight, where Gondelman worked as a staff writer for four years before joining Desus & Mero.

Gondelman’s desk is sparse. The only mainstays are a loose stack of scripts, a giant glass jar with a handful of Hershey kisses, a Red Sox ball cap and a day planner with most evenings penciled in. Despite the demands of his day job, Gondelman still performs standup around the city a few times a week.

The candy jar, a gift from his mother-in-law, is the most personal item. “It will help you make friends,” she reportedly said to Gondelman and continues to gift him bags of candy every holiday season. Eventually the quantity of candy proved “more than grown ups have the appetite for.”

Related: Director Paul Feig Shows Us His Impeccable LA Office

From behind his desk, Gondelman pulls out a few items he has yet to unpack — bobbleheads of John Oliver and Notorious B.I.G. (a natural pairing); an unopened can of “summer coffee pale ale,” a collaboration between Dunkin’ and Harpoon Brewery (a most unnatural pairing) and a Marcus Smart Celtics jersey.

(Daniel Shapiro for InsideHook)

Not Jayson Tatum, the rising superstar? “Jayson Tatum is the star,” says Gondelman, “but Marcus Smart is the guy.” The guy who, despite his unremarkable stats, keeps morale high and brings energy to every game and intensity to every play.

Gondelman, in some ways, plays a similar role in the writers’ room as Smart does for the Celtics. Gondelman repeatedly emphasizes how important it is to make his writers “feel supported and encouraged and unafraid to be themselves,” while also “being clear with feedback.” One quickly senses a wellspring of warmth from Gondelman and this generous good will simultaneously puts everyone at ease and urges them to perform their very best.

(Daniel Shapiro for InsideHook)

Having an open, healthy work environment is especially important for a freewheeling show like Desus & Mero, which is far more extemporaneous than most late-night shows. Rather than writing and rewriting a script to be very precise, as Gondelman did for Last Week Tonight, the goal with Desus & Mero, which relies heavily on improv, is to put the hosts in a situation where their humor and talents can best shine.

While this may sound like less work for the writers, it can be just as difficult, if not more so, to calibrate an environment for optimal improvisation. On show days, the writers huddle on set and, with Julia Young as their spokesperson, volley questions, and sometimes shade, for Desus and Mero to riff off of. “Occasionally,” Gondelman tells me, “they’ll shout out me if they want to make fun of the Red Sox.”

(Daniel Shapiro for InsideHook)

This greater responsibility and new challenge is part of what lured Gondelman to work for Desus & Mero. “I wanted to round out my TV education,” he said. In addition to writing, Gondelman is in the field shooting, pitching guests, and helping edit an hour of recorded content down to just 15-20 minutes that will be included in the show.

If he could, Gondelman would eschew desks entirely. He prefers writing horizontally: posting up on a couch with a laptop perched on his belly, arms hairpinned like a T-Rex’s, chin sandwiched. That’s how he wrote his essay collection, Nice Try. “I just want to be exercising my brain as much as I can and my body as little as I can when I’m writing,” says Gondelman and pauses. “Which is also how I behave when I’m not writing.”

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