Theater Wit just extended its current hit show, the Midwest Premiere of Itamar Moses’s The Ally, an additional two weeks.
And the Lakeview-based company is riding that positive momentum with today’s announcement of a full, four-play season in 2026-27: the Chicago Premiere of Tim Venable’s Adolescent Salvation, the return of its holiday season smash hit Who’s Holiday!, and the Chicago premieres of Dead Outlaw, book by frequent Wit collaborator Itamar Moses, in a co-production with Porchlight Music Theatre, and Joshua Harmon’s latest work, We Had a World.
“This is a season that will bring three premieres to Chicago, introducing new playwrights Tim Venable alongside beloved writers like Itamar Moses and Joshua Harmon. Adding in the sixth year of Who’s Holiday—Chicago’s new Christmas tradition, this season marks our first full production schedule since 2019, an accomplishment for which we have Chicago audiences and donors to thank. It’s going to be a very fun year. For all of us,” said Theater Wit Artistic Director Jeremy Wechsler.
August brings the Chicago premiere of Adolescent Salvation by Tim Venable, directed by Guillermo Cienfuegos. Critically acclaimed in its L.A. world premiere last year, Adolescent Salvation dares to portray adolescence in all its abundance of contradictions: sloppy, raw, and deeply human. Stage and Cinema wrote it "lurches, it burns, it contradicts itself — alive in ways most new plays are not." Performances are August 14-October 4. Press Opening Night is Monday, August 24 at 7 p.m.
Back for its sixth consecutive holiday season is Who’s Holiday!, one of Chicago’s favorite late-night holiday comedies. Chicago musical theater queen Veronica Garza and director Christopher Pazdernick return to retell the hilarious, sordid, and yes, sentimental tale of all that harrowing things that happened to Cindy-Lou Who after she met The Grinch. Performances are November 27-December 27. Press Opening Night is Friday, November 27 at 7 p.m.
Next, Theater Wit presents the Chicago Premiere of Dead Outlaw, the 2025 Tony Award-nominated Best Musical, in a co-production with Porchlight Music Theatre. This wickedly irreverent musical tale, based on the true story of bumbling bandit Elmer McCurdy, is “a truly one-of-a-kind production” (Entertainment Weekly). Music and lyrics are by David Yazbek and Erik Della Penna. Book by Tony Award-winner Itamar Moses, a Theater Wit favorite. Artistic Director Jeremy Wechsler directs and Brenda Didier is choreographer. Performances are February 10-March 21, 2027 in the Začek McVay Mainstage Theater at The Biograph Theater, 2433 N. Lincoln Ave. Press Opening Night is Sunday, February 14, 2027.
For its 2026-27 finale, Wechsler continues his celebrated collaboration with playwright Joshua Harmon (Bad Jews, Admissions, and most recently, their hit production Prayer for the French Republic) with Harmon’s newest play, We Had a World. This Theater Wit Chicago premiere is the story of a dying woman who asks her grandson to write a play about their family — with a caveat that he make it "as bitter and vitriolic as possible.” What unfolds is a searing, funny, and deeply personal recreation of thirty years of family fights, monstrous behavior, enormous cruelty, and enduring love. Performances are March 12-April 25, 2027. Press Opening Night is Monday, March 22 at 7 p.m.
Tickets to Theater Wit’s first 2026-27 season production, Adolescent Salvation, go on sale Friday, May 1. Purchase tickets at theaterwit.org, call (773) 975-8150, or purchase in person at the Theater Wit box office.
Better yet, a great way to support Chicago’s storefront theater scene is to purchase a Theater Wit Membership. For a low monthly fee of $35 – often less than the price of a single ticket – $25 for students, and $62 for a dual membership - Theater Wit members see as many shows as they want on the company’s three stages, both Theater Wit productions, resident, and visiting companies, year round. Sign up at theaterwit.org/boxoffice/membership.
Theater Wit is located at 1229 W. Belmont Ave., in Chicago’s Lake View neighborhood. Convenient parking is available for $10 across Belmont in the lot behind Kubo restaurant (pay at the Theater Wit box office.) Neighborhood street parking is available, as are private paid lots (tip: book ahead and at a discount with Spothero). Theater Wit is also accessible via the CTA 77 Belmont bus, and is three blocks west of the CTA Belmont Red/Brown/Purple line stop.
To learn more, visit theaterwit.org or follow the company on Facebook or Instagram.
Theater Wit’s 2026-27 Season: More About the Plays
Adolescent Salvation
by Tim Venable
directed by Guillermo Cienfeugos
August 14-October 4, 2026
Press Opening: Monday, August 24 at 7 p.m.
Tickets: $18–$46
Over the course of one night, through a haze of tequila, texting, and Taylor Swift, three teenagers banter, bicker, and push each other to the edge of danger — with consequences that could prove lethal. It begins light and funny, then shifts into something far darker, its tonal shifts as natural as the mood swings of youth. A play that lingers long after the curtain, Adolescent Salvation dares to portray adolescence in all its abundance of contradictions: sloppy, raw, and deeply human.
Tim Venable's audacious new play "lurches, it burns, it contradicts itself — alive in ways most new plays are not" (Stage and Cinema). StageScene LA called it "one humdinger of a stunner." Venable is a writer/director/actor/ producer, originally from Iowa, a graduate of Illinois State University, currently in L.A. His plays include Baby Foot, The Beautiful People, Blue Roses and Crystal Gayle is a Beautiful Lady.
Guillermo Cienfuegos is the directing pseudonym of L.A. actor Alex Fernandez. Under both names, he has had an extensive 30 year career as a director and actor in theater, television, feature films and voice over. He directed the world premiere of Adolescent Salvation in November 2025 at Rogue Machine, where he serves as Artistic Director.
Cienfuegos describes Venable’s play as "dangerous, uncompromising, and darkly funny,” a production that locks audiences in from the first moment, leaving them "laughing, wincing, and reflecting in equal measure" (LA Theatrix).
Who’s Holiday!
by Matthew Lombardo
directed by Christopher Pazdernik
featuring Veronica Garza as Cindy Lou-Who
November 27-December 27, 2026
Opening Night: Friday, November 28 at 7 p.m.
Veronica Garza as Cindy Lou in Who's Holiday! in 2025. Credit: Noelle Harrison
Adults-only holiday fun: Who's Holiday! brings R-rated Cindy-Lou Who back to Theater Wit for her sixth consecutive year.
Veronica Garza, who originated the role in Chicago and was Jeff-nominated, returns as Cindy-Lou Who, now 40, flirty, and ready to spill the green tea about the Grinch.
Step inside the city's #1 holiday bedazzled mobile home, where Cindy-Lou is pre-gaming for her big party with Yertle the Turtle, The Lorax, Thing One, and Thing Two. She also serves the audience party snacks plus a shot of Malort before revealing the shocking true story of everything that happened following her Christmas Eve encounter with the Grinch.
Trigger warning: While told exclusively in Seussian rhyme, Cindy-Lou Who’s story is also R-rated. That’s why tickets for children 12 and under are $500. Don’t bring them.
Dead Outlaw
Music and Lyrics by David Yazbek and Erik Della Penna
Book by Itamar Moses
Directed by Jeremy Wechsler
Choreographed by Brenda Didier
Co-Production with Porchlight Music Theatre
Začek McVay Mainstage Theater at The Biograph Theater, 2433 N. Lincoln Ave.
February 10-March 21, 2027
Press Opening Night: Sunday, February 14, 2027
The 2025 Tony Award-nominated for Best Musical and winner of three Best Musical awards (Drama Desk, Outer Critics Circle and New York Drama Critics’ Circle), Dead Outlaw is a wickedly irreverent tale based on the true story of bumbling bandit Elmer McCurdy. This dark comedy spanning more than a century delves into themes of fame and its repercussions as McCurdy’s mummified body becomes a traveling curiosity across America and beyond.
Entertainment Weekly calls the Tony-nominated new musical “a truly one-of-a-kind production, complete with a whole lot of laughs and a surprising amount of heart. It needs to be seen to be believed!”
We Had a World
Chicago Premiere
by Joshua Harmon
directed by Jeremy Wechsler
March 12–April 25, 2027
Press Opening Night: Monday, March 22, 2027 at 7 p.m.
Theater Wit Artistic Director Jeremy Wechsler continues his celebrated collaboration with playwright Joshua Harmon with the Chicago premiere of We Had a World. When a dying woman calls her grandson and asks him to write a play about their family — with a caveat that he make it "as bitter and vitriolic as possible" — what unfolds is a searing, funny, and deeply personal recreation of thirty years of family fights, monstrous behavior, enormous cruelty, and enduring love.
We Had a World premiered off Broadway in May 2025 at the Manhattan Theatre Club. “Rooted in a multigenerational Jewish family, Harmon has a gift for finding the universal in the specific, and the result is one of his most intimate and nakedly autobiographical works yet.” (Stage and Cinema) Exeunt Magazine NYC wrote Harmon “traces a young man's relationship with both his mother and his grandmother — learning about art, theater, and the movies from one, and how (and how not) to conduct yourself in the world from the other.”
Wechsler and Harmon (Bad Jews, Admissions) have consistently brought some of the most exciting creative partnerships in Chicago theater, most recently showcased in their hit production of Prayer for the French Republic, which captivated Chicago audiences and cemented Theater Wit's reputation as a home for vital, ambitious new work.
“We Had a World marks the next chapter in that ongoing conversation between a playwright at the height of his powers,” said Wechsler, “and the Chicago company that has long championed his voice.”
Just extended at Theater Wit: The hit Midwest Premiere of The Ally by Tony Award-winner Itamar Moses
(photo left) DeVaughn Asante Loman (left) as Baron and Jordan Lane Shappell as Asaf in Theater Wit’s The Ally. (photo right) Jordan Lane Shappell (left) as Asaf and K Chinthana Sotakoun as Gwen. Credit: Charles Osgood
Due to popular demand, Theater Wit has extended its Midwest premiere of The Ally, its current collaboration with playwright Itamar Moses, through May 17. The updated performance schedule, including newly-added Saturday matinees, is Thursday and Friday at 7 p.m.; Saturday at 2 and 7 p.m.; and Sunday at 2 p.m. Tickets are $18-$44. Purchase tickets at theaterwit.org, by calling (773) 975-8150, or in person at the Theater Wit box office.
Itamar Moses, author of The Band's Visit, was also a finalist for the 2025 Pulitzer Prize for The Ally, a provocative new play about identity, loyalty, and the complexities of unity. Jeremy Wechsler (Prayer for the French Republic) directs. The Chicago Reader wrote ““Heady and passionate questions,” The Ally “explodes with rhetoric and recrimination—mostly around Israel and Palestine, but also touching on a host of other urgent issues.
About Theater Wit, Chicago’s “Smart Art” theater
Photos courtesy Theater Wit
As a production company, Theater Wit is the premier smart art theater in Chicago, producing humorous, challenging, and intelligent plays that speak with a vibrant and contemporary theatrical voice. As an institution, Theater Wit seeks to be the hub of the Chicago neighborhood theater scene. Led by Artistic Director Jeremy Wechsler, Wit brings together Chicago’s best storefront theater companies in its three, 99-seat spaces, where audiences find a smorgasbord of excellent productions, see the work of a parade of talented artists, and mingle with audiences from all over Chicago.
In Fall 2025, Theater Wit received a three-year, $600,000 grant from the Paul M. Angell Foundation in support of Theater Wit’s Shared Spaces program, which empowers the artistic work of independent itinerant theater producers through subsidized, affordable space rentals and tailored production, accessibility and administrative support.
In addition to Theater Wit’s The Ally, productions playing this spring at Theater Wit include resident company Shattered Globe Theatre’s World Premiere of Paul W. Kruse’s Eelpout!, now through May 30; and visiting company The Artistic Home’s The Sugar Wife, now through May 3.
A great way to show support for Chicago storefront theater is to purchase a Theater Wit Membership. For a low monthly fee of $35 – often less than the price of a single ticket – $25 for students, and $62 for a dual membership - Theater Wit members see as many shows as they want on the company’s three stages, year round. Sign up at theaterwit.org/boxoffice/membership.