WITS END: Jay Jurden vs. Chloe Radcliffe | Comedy Trivia Gameshow

Schedule

Wed Sep 23 2026 at 07:00 pm to 10:00 pm

UTC-04:00
Location

littlefield | Brooklyn, NY

Comedians Jay Jurden & Chloe Radcliffe face off in NYC’s funniest anarchic live comedy trivia game show at Littlefield. Doors 7p | Show 8p
About this Event

SEPT 23 - DOORS 7PM | SHOW 8PM

Comedians Jay Jurden and Chloe Radcliffe (and special guests) bring their brains to WITS END, the live comedy trivia game show hosted by Adam Kesner, where comedians compete in trivia tailored specifically to their weird little niches.

Every show is completely new and written just for that night’s players. Expect the kind of competitive energy usually reserved for siblings who’ve been training their whole lives for this moment to crush each other.

WITS END is a live comedy game show, hosted by Adam Kesner, where two celebrity comedians lovingly compete in a game of trivia built around their personal obsessions and areas of expertise. Contestants get real trivia experts on their teams, the audience plays along, and everyone leaves feeling a little smarter and LOT sillier, with some pulls from the bags of mystery and misery along the way. Oh, and if no one knows the answer, the funniest wrong answer wins.

Think Jeopardy, if it was held in Pee-Wee's Playhouse.

WITS END is created and hosted by Adam Kesner, who has a 20-year career as a Trivia host and owns and operates TRIVIAL DISPUTE, which provides his unique blend of comedy and trivia to bars in NYC as well as events around the country. This show is his dream.

"I didn't realize this was a career," said ADAM KESNER - Wall Street Journal

WITS END past guests include David Cross, Eugene Mirman, Wyatt Cenac, Samantha Bee, John Hodgman, Josh Gondelman, Phoebe Robinson, Jon Glaser, H. Jon Benjamin, Dylan Adler, Sam Morrison, Kristen Schaal, Kurt Braunholer, Martin Urbano, Reggie Watts, Connor Ratliff, Griffin Newman, Nico Carney, Connor Janda + many more

FOR MORE INFO, PLEASE GO TO WITSENDGAMESHOW.COM OR CONTACT [email protected]

Featuring:

Jay Jurden is a New York-based comedian, writer, and actor. Originally from Mississippi, Jay regularly performs comedy all over the country. He was recently a Staff Writer for Apple TV+'s Emmy-nominated show, The Problem With Jon Stewart. He has performed on The Tonight Show Starring Jimmy Fallon three times and has also been seen on The Late Show with Stephen Colbert and HBO's High Maintenance. He was named one of Variety's 10 Comics to Watch in 2022. His album, Jay Jurden Y'all, debuted #1 on iTunes. Jay has written for numerous publications including Vulture, Teen Vogue, McSweeney's, and The New Yorker. He has also written for Marvel's Voices: X-Men #1. He was listed on Vulture's Comedians You Should and Will Know in 2020 and was selected to be featured in Just for Laughs Festival's New Faces in 2019.

Chloe Radcliffe can be seen in Bradley Cooper’s latest film Is This Thing On? She was named a Just For Laughs 2025 New Face, along with one of Deadline’s 15 Comedians Ready To Break Out In 2025, and one of Vulture’s Comedians You Should And Will Know. She hosts In Tandem with Chloe Radcliffe, where she interviews other comedians while they ride a tandem bike together. Her one-woman show CHEAT, about her history of infidelity, led The New York Times’ recommendations for the New York Comedy Festival. She sold out her full-month run at the 2023 Edinburgh Fringe Festival, with reviews calling it, “Hilarious and sharply-crafted” (Deadline), “Worthy of the greats like Mike Birbiglia” (Chortle), and “A new take on an old topic, with hard-hitting punchlines” (The New York Times). Chloe is currently developing CHEAT for tv. She starred in Steven Soderbergh’s COMMAND Z, and was nominated for a 2024 WGA award for her writing on the series. She has been seen on Comedy Central, Don’t Tell Comedy, and After Midnight with Taylor Tomlinson. She was a staff writer on The Tonight Show with Jimmy Fallon, has a comedy feature in development with Sony, and was named a TBS Comic To Watch at the New York Comedy Festival.

Hosted by:

Adam Kesner is the Minister of Information at Wit’s End. Under the name Trivial Dispute, he’s spent the past 15 years writing and hosting the most raucous, high-energy trivia nights in NYC, as well as corporate workshops, team-building events, and private events for clients like Google, American Express, Tommy Hilfiger, A24, Magnolia Films, and more. He’s hosted games everywhere from bars to breweries to Brooklyn block parties to under the Blue Whale in the Museum of Natural History. For the past 5 years, he’s also hosted a weekly streaming Trivia Game Show on Twitch, with hundreds of teams playing from around the world.

Directed by:

Ryan Cunningham (she/her) is an award-winning queer writer/director and Emmy and Peabody award-winning producer in film, television, and theater - primarily in comedy. Over her career, she has produced, directed, and/or developed over 70 projects, including 20 scripted comedy series, 8 feature films, 25 stand-up specials, and 6 Off-Broadway plays. Her feature directorial debut, Lone Wolves, is now streaming on Amazon Prime. Her second feature, Music Therapy, goes into production in November 2026.

Directing credits: Sugar Daddy’s extended, award-nominated off-Broadway run (SoHo Playhouse, SoHo Theatre London), Samantha Bee presents Wits End (NYCF, SXSW), Alan Cumming’s Club Cumming Presents a Queer Comedy Extravaganza! (Showtime), Ilana Glazer: The Planet is Burning (Amazon), Expecting Amy (HBO Max), the award-winning feature Lone Wolves (Amazon), and the upcoming pilot Whisper Sisters, starring Mae Whitman, Emily Meade, and Henry Thomas.

TV producing credits include Broad City (Comedy Central), Search Party (TBS/HBO Max), Inside Amy Schumer (Comedy Central), The Last O.G. (TBS) & Ziwe (Showtime).

Ryan is a graduate of Rhode Island School of Design and a Trustee on RISD’s Board.

Produced by:

Olivia Wingate’s credits in TV include: Maron (IFC) which ran for four seasons, Bobcat Goldthwait’s Misfits & Monsters (Tru TV), and Joe Mande’s Award Winning Standup Special (Netflix), Why Shit So Crazy (Netflix), John Hodgman’s Ragnarok (Netflix), Wyatt Cenac’s Brooklyn (Netflix) and An Evening Of Comedy In An Fake Underground Laboratory (Comedy Central). In film, Olivia produced the documentary feature It Started As A Joke which premiered at SXSW 2019, and premiered her narrative feature We Strangers at SXSW 2024. Upcoming projects include features by Bobcat Goldthwait, Stephen Belber, and Samuel D. Hunter.

Where is it happening?

littlefield, 635 Sackett Street, Brooklyn, United States
Tickets

USD 18.71 to USD 24.36

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