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DEAD OUTLAW and More Set For Theater Wit 2026-27 Season

The Lakeview company also extends its Midwest premiere of THE ALLY by two weeks

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DEAD OUTLAW and More Set For Theater Wit 2026-27 Season

Theater Wit has 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.

Adolescent Salvation

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.

Who's Holiday!

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.

Dead Outlaw

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.

We Had a World

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.

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More on Theater Wit
Upcoming Shows
Adolescent Salvation
8/14 - 10/4/2026
Vladimir
Vladimir
10/2 - 11/14/2026
Recent Articles
Review: Black Cat Theatre's ELEPHANT IN THE WOMB at Theater Wit
Review: Black Cat Theatre's ELEPHANT IN THE WOMB at Theater Wit
9/4/2026
Review: ADOLESCENT SALVATION at Theater Wit
Review: ADOLESCENT SALVATION at Theater Wit
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