Josh Gondelman

Here’s a full, in-depth profile on Josh Gondelman:

Josh Gondelman – Life, Career, and Many Voices

Discover the life and career of Josh Gondelman — the comedian, author, and writer behind You Blew It! and Nice Try. From stand-up stages and Twitter parody to Emmy-winning TV writing, explore his journey, style, philosophy, and memorable quotes.

Introduction

Josh Gondelman (born January 15, 1985) is an American writer, comedian, and author who bridges multiple creative worlds. He writes satire and personal essays, performs stand-up, and crafts television scripts—most notably for Last Week Tonight with John Oliver and Desus & Mero. His voice is distinct for its mix of warmth, self-deprecation, and observational wit.

Though he’s often thought of primarily as a comedy writer, Gondelman has also established himself as an author of essays and a cultural commentator, navigating the boundaries between humor and sincerity in modern life.

Early Life and Education

Joshua Lyons Gondelman was born on January 15, 1985 in Stoneham, Massachusetts.

He graduated from Stoneham High School in 2003. (Brandeis University, graduating in 2007 with a double major in creative writing and English, and a minor in Spanish.

During and after college, he developed his comedic voice through writing and performing. In his early adulthood, he lived for a time in Boston, where he honed his stand-up style and began publishing comedic essays and shorter works.

Career and Achievements

Stand-up & Early Writing

Gondelman began doing stand-up comedy around age 19 in the Boston area.

Alongside stand-up, he published comedic essays and pieces, contributing to outlets such as McSweeney’s Internet Tendency, New York Magazine, The New Yorker, and others. (New York magazine in 2012.

He also co-created the parody Twitter account @SeinfeldToday, which reimagined Seinfeld characters in modern social media contexts. The account became quite popular.

Television Writing & Production

In 2014, Gondelman joined Last Week Tonight with John Oliver as a web producer for the show’s first season.

During his time there, he earned Emmy Awards for Outstanding Writing for a Variety Series, among other accolades.

In more recent years, he moved on to Desus & Mero (Showtime) as a supervising producer and writer.

He also contributed writing to the final season of The Marvelous Mrs. Maisel.

Published Works & Essays

Gondelman is the author (or co-author) of several books:

• You Blew It!: An Awkward Look at the Many Ways in Which You’ve Already Ruined Your Life (co-authored with Joe Berkowitz, published in October 2015)

• Nice Try: Stories of Best Intentions and Mixed Results (essay collection, published in September 2019 by Harper Perennial)

In Nice Try, he blends humor, introspection, and the awkward realities of daily life, giving readers insight into his style beyond stand-up.

He has also released comedy albums and specials. For example:

• Physical Whisper (2016) — a comedy album that performed well on iTunes and charted on Billboard.

• Dancing on a Weeknight (2019) — album/special.

• People Pleaser (2022) — his debut stand-up special produced by Comedy Dynamics.

• Positive Reinforcement (2025) — a newer stand-up special.

He has also appeared on television talk and comedy shows (e.g. Conan, Late Night with Seth Meyers, The Late Late Show with James Corden) and is frequently heard on NPR’s Wait Wait… Don’t Tell Me! as a panelist.

Style, Themes & Voice

Warmth, Kindness & Relatable Humor

One of Gondelman’s signature qualities is his capacity to mix kindness and humility into his humor. He often centers ordinary, even awkward, human experiences and turns them into moments of comic reflection.

Self-Deprecation & Insecurity

He doesn’t shy away from exposing his own foibles, failures, and insecurities—these become a source of connection rather than distance.

Observation & Mundanity

Gondelman draws material from everyday life: relationships, parenting (even vicariously), small disappointments, social media, and interior monologues. This grounds his humor in the familiar.

Meta and Literary Allusions

Given his background in writing and his involvement with SeinfeldToday, you’ll find references, literary play, and cultural satire woven into his work.

Blending Humor with Seriousness

While primarily comedic, Gondelman can turn toward poignancy—reflecting on mortality, identity, or the strain of modern life—in ways that resonate emotionally rather than just for laughs.

Legacy & Influence

• Gondelman is part of a newer wave of comedians who straddle stand-up, digital media, essay writing, and television.

• Through Nice Try and his essays, he shows how comedy and authentic self-expression can coexist in the written form.

• His work on Last Week Tonight and Desus & Mero situates him in the generation of comedic writers shaping the tone of late-night and satirical commentary.

• His approach—being generous, self-effacing, thoughtful—offers a counterpoint to aggressively edgy or confrontational humor, and has influenced peers and audiences who prefer a gentler comedic voice.

Personality & Personal Life

Gondelman is often described as kind, modest, and introspective. He brings a warmth to interviews and public appearances, and he maintains a presence that feels accessible rather than distant.

He is married to Maris Kreizman, a writer, editor, and creator in her own right (best known for Slaughterhouse 90210).

Gondelman has also been candid about mental health, the creative process, and balancing optimism with realism—his public persona often models humility and generosity.

Selected Quotes

Here are some quotes attributed to Josh Gondelman or reflecting his voice:

“It’s about creating a feeling of warmth along with humor.” (on his comedic style)

“I’m not, by nature, a confrontational person.” (Gondelman in GQ)

“I don’t know if I have a guiding philosophy, but I do believe in doing the small things well—listening, being curious, showing up.” (paraphrase of his public interviews)

(From You Blew It! / his essays) “We all screw up; the trick is learning how to apologize and keep going.”

These reflect his blend of humor, modesty, and introspection.

Lessons from Josh Gondelman

1. Be gentle, not slick
   You can build a comedic voice without resorting to harshness or cynicism.

2. Vulnerability builds connection
   Exposing uncertainty or failure can engage audiences more than polished certainty.

3. Diversify your voice
   Gondelman moves between stand-up, essays, Twitter parody, TV writing—showing that creative work need not stay in one lane.

4. Small moments, big insight
   Paying attention to everyday detail—awkward texts, pet behavior, interior monologues—can unlock universal echoes.

5. Balance ambition with humility
   His trajectory shows how one can succeed in large arenas (TV, books) without losing groundedness and self-awareness.

Conclusion

Josh Gondelman is more than a comedy writer: he is a multifaceted creator whose work spans stand-up, essays, TV, and digital media. His tone—warm, self-effacing, observant—offers a refreshing mode of comedic expression in a landscape often shaped by extremes. In his writings and performances, he invites us into the messy, awkward, affecting details of life.