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Special Preview of Windy City Comedy Fest is Coming To The Den Theatre

Acts include Rick Glassman, “Beach Too Sandy, Water Too Wet” Podcast, and more.

By: Jun. 17, 2024
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The Den Theatre will present a special Windy City Comedy Fest event previewing the inaugural edition of the festival set for 2025, featuring top Chicago comedians Kristen Toomey, Junior Stopka, Dwayne Kennedy, and Ariel Julie. This one-night-only special event will be held Thursday, August 8, 2024, at 7:15 p.m. at The Heath Mainstage, 1331 N. Milwaukee Ave. in Chicago’s Wicker Park neighborhood.

Tickets are now on sale at or by calling (773) 697-3830.

The best comedians in Chicago are coming together for one night only to raise money for the first annual Windy City Comedy Fest (coming in 2025), which is sure to be an event of incredible comedy unlike any other! Join us at Wicker Park's favorite spot for comedy, The Den Theatre, on August 8th, 2024, at 7 p.m. to see Chicago's best: Kristen Toomey, Junior Stopka, and Dwayne Kennedy; three comics with careers spanning decades with original material covering every topic under the sun. Hosted by Ariel Julie, a seasoned Chicago comic full of energy, charisma, and a wry sense of humor, this is a must-see comedy event of epic proportions that you do not wanna miss! 

Kristen Toomey’s standup career began in 2008. Since then, she has headlined comedy clubs all over North America and the UK. Her recent micro special, produced by Zanies Chicago, was well received with over 300K views. Currently, with back-to-back viral reels amassing 20M+ views, her follower count continues to skyrocket. Kristen's comedy style is unapologetically truthful and energetic, earning her the title of "Chicago Original" by The A.V. Club. Her debut album, Mother. Fucker, hit #1 on iTunes, cementing her status as a force to be reckoned with. She is regularly seen at the top clubs in New York and Chicago, like The Stand, New York Comedy Club, Zanies, and Laugh Factory. Kristen has performed at numerous festivals, such as the prestigious Just For Laughs in Montreal, 312 Comedy Festival, Oddball Festival, Flyover in St. Louis, and more. She has opened for Chris Redd, Janelle James, Kyle Kinane, Natasha Leggero, Kevin Nealon, and April Macie. You can currently see her standup on Kevin Hart’s LOL! Network and Comedy In Color streaming on Peacock.

Junior Stopka was born and raised in the heart of Chicago and has been making waves on the national comedy stage since 2007. Having appeared on Comedy Central, NBC's "Last Comic Standing", Dave Attell's Comedy Underground, and a staple of Doug Stanhope's national tours for nearly a decade, Junior's original take on every topic under the sun is as bold and broad as you'd like, and he's as funny as he is original. His comedy brings this form of entertainment to a level of artistic expression rarely seen, making his act a must-see for any true comedy fan.  

Dwayne Kennedy is a stand-up comedian, actor, and writer. As a producer, he won a 2019 Emmy Award for the CNN original series United Shades of America. Described as a “world-class stand-up” by The Village Voice and “legendary” by the Chicago Tribune, Dwayne is one of the funniest, most thought-provoking, and influential comedians of our time. His satirical diversions and piercing perspective on social and world issues showcase a comedic genius heralded by the likes of Chris Rock and Marc Maron. Winner of Best Comedian at the 2002 HBO US Comedy Arts Festival in Aspen, Dwayne has performed on The Late Show with David Letterman, Late Night with Conan O'Brien, Jimmy Kimmel Live, The New Negroes and has both a Comedy Central Presents and Showtime special. A former writer and correspondent for the Chris Rock-produced, critically acclaimed FX original series, Totally Biased with W. Kamau Bell, Dwayne has also written for The Arsenio Hall Show (CBS) and The Orlando Jones Show (FX). Dwayne’s acting credits include roles on such classic series as Seinfeld, Martin, 227, Amen, and the upcoming Lindy West/ Ahamefule J Oluo penned indie-film Thin Skin. After self-releasing his debut EP in 2016, his first full-length comedy album, Who The Hell Is Dwayne Kennedy? comes out on Oak Head Records in May 2020. The album was produced by Ahamefule J. Oluo and co-produced by comedians W. Kamau Bell and Hari Kondabolu.

From Chicago, Ariel Julie combines sass and crass in her brutally honest style of comedy and storytelling. She has performed at comedy clubs and festivals across the country, bringing her unique brand of humor to audiences of all kinds. At a towering 4'10", Ariel Julie is proof that the best, funniest things can come in the smallest, most Jewish of packages. Her full-hour, Weiner Patrol, is available on YouTube.

Also appearing at The Den Theatre in August 2024:

Rick Glassman
Saturday, August 3, 2024 at 7:15 p.m. and 9:30 p.m.
Tickets: $22 - $40

Beach Too Sandy, Water Too Wet Podcast
Thursday, August 15, 2024, at 7:15 p.m.
Tickets: $25 - $47.50

Jiaoying Summers
Friday, August 16, 2024 at 7:15 p.m. and 9:30 p.m.
Tickets: $22 - $50

Daniel Weingarten
Friday, August 16, 2024, at 7:00 p.m.
Saturday, August 17, 2024, at 7:00 p.m.
Tickets: $26 General Admission 

Saturday, August 17, 2024, at 7:15 p.m. and 9:30 p.m.
Tickets: $25 - $45

José Rafael Guzmán 
Sunday, August 18, 2024 at 7:15 p.m.
Tickets: $22 - $40

Keith Pedro
Sunday, August 25, 2024 at 7:15 p.m.
Tickets: $22 - $37


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