Dream Big

Not many people can claim landing one dream job after another.

But that's the case for Josh Gondelman, who moved from HBO's Last Week Tonight with John Oliver — where he won three Emmys for writing — to Showtime's Desus & Mero, where he is a writer and producer.

Ever since Gondelman left his Boston stand-up career behind eight years ago to test himself in New York, he's been collecting major credits.

His résumé includes performing stand-up on Conan, Late Night with Seth Meyers and The Late Late Show with James Corden; he's recorded three comedy albums; and he cocreated a Twitter sensation — the brilliant @SeinfeldToday account — with Jack Moore.

Gondelman is an author, too. He cowrote the humorous 2015 book You Blew It! An Awkward Look at the Many Ways in Which You've Already Ruined Your Life with Joe Berkowitz. This fall, he'll release a solo book of essays, Nice Try: Stories of Best Intentions and Mixed Results.

All the pieces grapple with making an earnest effort but failing. To wit: one essay is about "a failed attempt to do drugs in a bowling alley," he says, while another chronicles how he and his wife, writer Maris Kreizman, acquired their dog "by accident through a really untrustworthy distant acquaintance of an acquaintance."

Gondelman — whose fallback career was teaching — says he learns from every opportunity. "I don't think I could have gotten a better clinic in rigorous joke-writing and clarity of point-making, and marrying those two together," he says of his time as a staff writer on Last Week Tonight. He was promoted to that role after working one season as a web producer for the show.

Now he's developing different creative muscles on Desus & Mero, where he works closely with the graphics team and editors.

"It is an extensive edit for a late-night show," he explains. "Most shows come in knowing what is going on the air and having to make a couple of little trims for time. But we're constructing the arc of the show from the material that happens onstage a lot of the time. So, it's a different workflow and challenge." And "very fun," he adds. As every dream job should be.

This article originally appeared in emmy magazine, Issue No. 8, 2019