Steppenwolf Theatre is pleased to present five-time Emmy Award winner Jane Lynch, the hilariously charming Kate Flannery and The Tony Guerrero Quartet in The Trouble With Angels, a raucous night of comedy, song and unapologetic mischief playing four performances only, April 9 – 11, 2026 in Steppenwolf’s Downstairs Theater, 1650 N. Halsted St in Chicago. Tickets cost $79 - $149*. Tickets go on sale at steppenwolf.org/angels or by calling the Box Office at (312) 335-1650. *Prices include a $10 processing fee.
With powerhouse vocals, razor-sharp wit and more than a few surprises, these two beloved stars serve up a cocktail of classic tunes, campy banter and devilish charm. It’s part cabaret, part stand-up and all sass – because when these angels get together, heaven can wait.
Kate Flannery and Jane Lynch in a publicity image for "The Trouble with Angels." Photo by Chris Haston.
Performance Schedule
Thursday, April 9, 2026 at 7:30 pm
Friday, April 10, 2026 at 7:30 pm
Saturday, April 11, 2026 at 3 pm & 7:30 pm
Artist Biographies
Jane Lynch is a five-time Emmy winner known for her portrayal of Sue Sylvester on Glee. She currently hosts NBC’s Weakest Link and appears in Only Murders in the Building on Hulu. Additional television credits include The Marvelous Mrs. Maisel, The Good Fight and Two and a Half Men. Lynch’s film credits include The 40-Year-Old Virgin, Julie & Julia and Best In Show. Along with Kate Flannery, Tim Davis and The Tony Guerrero Quintet, Jane tours the country with their annual holiday show, A Swingin’ Little Christmas. The album is available on all music platforms.
Kate Flannery is best known for her nine seasons as Meredith the drunk on NBC’s The Office. Kate was a fan favorite on Season 28 of ABC’s Dancing With The Stars, touring live at Radio City Musical Hall and 40 cities. Television guest star appearances include Magnum P. I., Young Sheldon and Brooklyn Nine Nine. She can be seen in dozens of indie films including The Prank with Rita Moreno.
The Tony Guerrero Quartet has been a staple of the Southern California jazz scene for many years. Featuring Tony Guerrero (trumpet/piano), Matt Johnson (drums), Mark Visher (sax/flute), Dave Siebels (keyboards) and David Miller (bass). Along with Jane Lynch, Kate Flannery and Tim Davis, the quintet tours the country with their annual holiday show, A Swingin’ Little Christmas. In 2016, they released the holiday album “A Swingin’ Little Christmas Time,” that landed a spot in the Top Ten of the Billboard Adult Contemporary charts. The title track, an original Tony Guerrero composition, went to #6 on the Billboard charts. The Tony Guerrero Quintet's own recordings have been a staple on jazz radio for over thirty years.
Accessibility
Steppenwolf is committed to making the theatergoing experience accessible to everyone. Assistive listening devices are available for every performance and all our spaces are equipped with an induction hearing loop. Our building features wheelchair accessible seating and restrooms, push-button entrances, a courtesy wheelchair and all-gender restrooms, with accessible counter and table spaces at our bars. For additional information regarding accessibility, visit steppenwolf.org/access. If you have questions or would like to make a specific request, email access@steppenwolf.org or call our box office at 312-335-1650.
Sponsor Information
United Airlines is the Official and Exclusive Airline of Steppenwolf. Steppenwolf is also grateful for the significant season support from lead sponsors Allstate Insurance Company, Paul M. Angell Family Foundation, Crown Family Philanthropies, Caroline and Keating Crown, Julius Frankel Foundation, Lefkofsky Family Foundation, Northern Trust, Anne and Don Phillips, John Hart and Carol Prins, Shubert Foundation, Inc, Walder Foundation, and Zell Family Foundation. Steppenwolf also acknowledges generous support from premier sponsors Anonymous, Andrew and Amy Bluhm, Michael and Cathy Brennan, Ann and Richard Carr, Chicago Community Trust, Steven and Nancy Crown, Conagra Brands Foundation, Rich and Margery Feitler, FROST CHICAGO, Joyce Foundation, Harold and Mimi Steinberg Charitable Trust, The Orlebeke Foundation, Polk Bros. Foundation, Bryan Traubert and Penny Pritzker, Sacks Family Foundation, Smart Family Foundation of Illinois, Thoma Bravo, and Vinci Restaurant. Steppenwolf also acknowledges support from the Illinois Arts Council and the Department of Cultural Affairs and Special Events.
About Steppenwolf Theatre Company:
Steppenwolf Theatre Company is the nation’s premier Ensemble Theater with 49 members who are among the top actors, playwrights and directors in the field. Thrilling, powerful, groundbreaking productions have made this theatre legendary. From the 1980 phenomenon of Balm in Gilead, to The Grapes of Wrath, August: Osage County, Downstate, The Brother/Sister Plays, and now, the 2025 Pulitzer Prize and Tony Award-winning Purpose, Steppenwolf Theatre has had a long-running and undeniable impact on American Theater and Chicago's cultural landscape. Founded in 1976, Steppenwolf started as a group of teens performing in the basement of a church. Today, the company's artistic force remains rooted in the original vision of its founders: an artist-driven theatre, whose vitality is defined by its appetite for bold and innovative work. Every aspect of Steppenwolf is rooted in its Ensemble ethos, from the intergenerational artistic programming to the multi-genre performance series LookOut, to the nationally recognized work of Steppenwolf Education and Engagement which serves nearly 15,000 teens annually. While grounded in the Chicago community, more than 40 original Steppenwolf productions have enjoyed success nationally and internationally, including Broadway, Off-Broadway, London, Sydney, Galway and Dublin. Steppenwolf also holds accolades that include the National Medal of Arts, 14 Tony Awards, two Pulitzer Prize-winning commissions and more. Led by Artistic Directors Glenn Davis and Audrey Francis, Executive Director Brooke Flanagan and Board of Trustees Chair Keating Crown — Steppenwolf continually redefines the boundaries of live theater and pushes the limits of acting and performance.
Steppenwolf’s Mission: Steppenwolf strives to create thrilling, courageous and provocative art in a thoughtful and inclusive environment. We succeed when we disrupt your routine with experiences that spark curiosity, empathy and joy. We invite you to join our ensemble as we navigate, together, our complex world. steppenwolf.org, facebook.com/steppenwolftheatre, twitter.com/steppenwolfthtr and instagram.com/steppenwolfthtr.