The Den Theatre Announces December Comedy Lineup Featuring Jerrod Carmichael, Langston Kerman, The Sklar Brothers & More

The Den Theatre has revealed its December 2025 comedy schedule at its Wicker Park stages, 1331 N. Milwaukee Ave. This month’s lineup includes John Achkar on December 2, Langston Kerman on December 4, Jerrod Carmichael December 6–11, Charlene Kaye’s Tiger Daughter (presented by Margaret Cho) on December 10, The Sklar Brothers on December 13, Gavin Matts on December 18, and IMHO: The Show’s New Year’s Eve Party on December 31.

John Achkar

Tuesday, December 2, 2025 at 7:15 p.m.
Tickets: $55–$95

Lebanese stand-up comedian, actor, and entrepreneur John Achkar brings his sharp wit and heartfelt storytelling to the Den. Known for his viral sketches and sold-out international tours, Achkar has performed across the Middle East, Europe, North America, and Australia. His latest special, AAM JARRIB (I’m Trying), explores trial, error, and the humor found in life’s unpredictability.

Langston Kerman

Thursday, December 4, 2025 at 7:15 p.m.
Tickets: $22–$40

Comedian and actor Langston Kerman—named by Vulture as one of the year’s best for his Netflix special Bad Poetry, directed by John Mulaney—returns to the stage. Kerman’s credits include Abbott Elementary, The Boys, Bust Down, and Insecure, as well as writing for Pause with Sam Jay and South Side. His podcast My Momma Told Me is part of Will Ferrell’s Big Money Players Network.

Jerrod Carmichael

Saturday–Thursday, December 6–11, 2025 at 7:00 p.m. (six performances)
Tickets: $28–$38

Emmy-winning comedian, writer, and actor Jerrod Carmichael (Rothaniel, The Carmichael Show) performs a six-night run. His most recent HBO special, Don’t Be Gay, follows the success of Rothaniel, and his current HBO reality series The Jerrod Carmichael Reality Show continues to showcase his candid, provocative style.

Charlene Kaye: Tiger Daughter (Presented by Margaret Cho)

Wednesday, December 10, 2025 at 7:15 p.m.
Tickets: $22–$40

Musician and comedian Charlene Kaye brings her acclaimed solo show Tiger Daughter: Or, How I Brought My Immigrant Mother Ultimate Shame—presented by Margaret Cho—to Chicago following sold-out runs at the Edinburgh Fringe and Melbourne International Comedy Festival. Directed by Jennifer Monaco, the show hilariously explores Kaye’s relationship with her mother and her journey from aspiring classical prodigy to rock-and-roll rebel.

The Sklar Brothers

Saturday, December 13, 2025 at 7:15 p.m. and 9:30 p.m.
Tickets: $22–$40

Randy and Jason Sklar, the identical twin comedians known for their appearances on Curb Your Enthusiasm, Better Call Saul, GLOW, and Entourage, bring their signature blend of fast-paced wit and observational humor. The Sklars also host the hit podcasts View from the Cheap Seats and Dumb People Town, the latter in development as an animated series with Sony and Will Arnett.

Gavin Matts

Thursday, December 18, 2025 at 7:15 p.m.
Tickets: $22–$37

Canadian-born, New York–based comedian Gavin Matts returns to the stage as he prepares for his second special. Named one of Vulture’s “Comedians You Should and Will Know,” Matts’s 2023 debut Progression earned praise from New York Magazine as “dark comedy at its best.” He has appeared on Comedy Central, Conan, Ramy, and Hacks.

IMHO: The Show – New Year’s Eve Party

Wednesday, December 31, 2025 at 9:30 p.m.
Tickets: $30–$55

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