Chicago’s Tony-Award winning Lookingglass Theatre Company, is proud to announce multi-award winner Anthony Rapp in the world premiere of a seasonal and intimate cabaret, Anthony Rapp: Home for the Holidays, December 17 - 20. Also, this December at Lookingglass is Lookingglass Presents, Monday, Dec. 8 at 6:30 p.m., an offering in partnership with Goodman’s Theatre’s 100 Acts of Free Theater and Lookingglass Young Ensemble celebrating the 250th anniversary of Jane Austen’s birth with their production of Emma, December 11 - 14. All performances take place at historic Water Tower Water Works, 163 E. Pearson St. at Michigan Ave. Tickets are now on sale for all events with additional information available at LookingglassTheatre.org.
"We are thrilled to welcome Anthony Rapp, other talented Chicago musicians and holiday revelers to Lookingglass Theatre this Holiday Season,” said Artistic Director Kasey Foster. “We love to celebrate and interact with our audiences -- and this cabaret, Home for the Holidays and the Lookingglass Presents are both fun and joyful ways to do so in a season that demands such!"
Anthony Rapp in Anthony Rapp: Home for the Holidays. Photo by Dave Rentauskus
ANTHONY RAPP: HOME FOR THE HOLIDAYS
December 17 - December 20
With Rick Bertone
Wednesday, Dec. 17 at 7 p.m., Thursday, Dec. 18 at 7 p.m., Friday. Dec. 19 at 7 p.m., Saturday, Dec. 20 at 2 p.m. and 7 p.m.
The Joan and Paul Theatre at Water Tower Water Works, 163 E. Pearson St. at Michigan Ave.
Ticket price: $55 - $340 (cabaret tables and standard seating available).
There’s nowhere star of Broadway stage and screen, Anthony Rapp (Rent, You’re a Good Man Charlie Brown, “Star Trek: Discovery”) would rather be than home, in Chicago, for the Holidays this December.
All are invited to experience an intimate holiday cabaret at Lookingglass Theatre accompanied by Rick Bertone and joined by some of Chicago’s favorite voices, this is a unique night that will leave audiences feeling merry and bright.
Monday, Dec. 8 at 6:30 p.m.
Lookingglass Bar and Café, 163 E. Pearson St. at Michigan Ave.
Tickets: FREE
Get to know Chicago in this fun-filled evening of variety entertainment and conversation with the latest edition of Lookingglass Presents. This free event is in partnership with Goodman Theatre’s 100 Free Acts of Theater and includes Actor and Star of the Lookingglass Holiday presentation Anthony Rapp: Home for the Holidays Anthony Rapp, Ensemble Member and Writer/Director of this winter Lookingglass production of White Rooster Matthew C. Yee and Chicago power couple: Don and Lisee.
(L to R) Artistic Director Kasey Foster and Brian Babylon at Lookingglass Presents, photo taken Monday, June 9. Photo by intheblackphotography.
Lookingglass Young Ensemble presents
December 11 - 14
Written by Kate Hamil
Based on the novel by Jane Austin
Directed by Heidi Stillman
Performance schedule: Thursday, Dec. 11 at 7:30 p.m., Friday, Dec. 12 at 7:30 p.m., Saturday, Dec. 13 at 2 and 7:30 p.m. and Sunday, Dec. 14 at 2 p.m.
The Joan and Paul Theatre at Water Tower Water Works, 163 E. Pearson St. at Michigan Ave.
Ticket price: $11 - $38
Emma Woodhouse knows everyone’s heart…except her own. Join the Lookingglass Young Ensemble for a delightfully modern twist on Jane Austen’s beloved novel, Emma. Emma Woodhouse is smart, spirited, outspoken … and trapped by a society that expects women to stay home and stay quiet. Emma occupies herself with neighborhood matchmaking but learns that even her sharp wits cannot control affairs of the heart.
As Emma takes the audience into her confidence and is swept away in the screwball comedy and enchanted by the way it speaks to today. Sharp, sweet and fun, the Young Ensemble invites all to join the party. See Emma with fresh eyes as Lookingglass celebrates the 250th anniversary of Jane Austen’s birth.
ABOUT ANTHONY RAPP
Anthony Rapp is thrilled to return to live and work in the city of his birth. Chicago is also where he earned his Equity card 45 years ago, when he was nine years old. He has since appeared on Broadway, Off-Broadway, in National Tours, at Regional Theatres and in films and on television. But his proudest work these days is as the father, with his husband Ken, of their two sons, Rai (aged 3) and Keony (aged 2).
ABOUT GOODMAN’S 100 FREE ACTS OF THEATER
Lookingglass Presents, Monday, Dec. 8 at 6:30 p.m., is in presented in partnership with the Goodman Theatre’s 100 Free Acts of Theater, a citywide year-long event that activates theater in all 50 wards of Chicago, co-presented by the Department of Culture Affairs and Special Events (DCASE). Designed as a celebration of the artistic fabric of Chicago, The Goodman is partnering with Lookingglass and organizations across the city during its Centennial Season to amplify existing programming and collaborate on new efforts.
All 100 acts are offered FREE, with participation open to Chicagoans of all ages and backgrounds. Learn more at GoodmanTheatre.org/100FreeActs.
ABOUT THE JOAN AND PAUL THEATRE
The main stage at the Water Tower Water Works has been named in honor of longtime Lookingglass supporters Joan and Paul Rubschlager and their transformational gift to ensure the future of Lookingglass. The couple have been instrumental in their partnership with Chicago organizations, such as Rush University and The Field Museum. Nationally, their support extends to the American Heart Association and Alzheimer's Association. The Joan and Paul Theatre reconfigures the stage and audience seating as dictated by the needs of each season, with a capacity of 200 persons including the balcony.
ABOUT LOOKINGGLASS THEATRE COMPANY
Founded in 1988 by graduates of Northwestern University, Lookingglass Theatre Company is a nationwide leader in the creation and presentation of new, cutting-edge theatrical works and in sharing its ensemble-based theatrical techniques with Chicago-area students and teachers through Education and Community Programs. Guided by an artistic vision centered on the core values of collaboration, transformation and invention, Lookingglass seeks to capture audiences’ imaginations leaving them changed, charged and empowered.
Recipient of the 2011 Tony Award for Outstanding Regional Theatre, Lookingglass has built a national reputation for artistic excellence and ensemble-based theatrical innovation. Notable world premieres include Mary Zimmerman’s Tony Award-winning Metamorphoses and The Odyssey, J. Nicole Brooks' Her Honor Jane Byrne, David Schwimmer’s adaptation of Upton Sinclair’s The Jungle and Studs Terkel’s Race: How Blacks and Whites Think and Feel about the American Obsession, Matthew C. Yee's Lucy and Charlie's Honeymoon and David Catlin’s circus tribute to Lewis Carroll, Lookingglass Alice, which was captured by HMS Media and reached 1.6 million PBS viewers.Looking Alice is now available to more than four million students worldwide through Digital Theatre+. Work created by Lookingglass artists has been produced in Australia, Europe and dozens of cities throughout the United States.
Anthony Rapp: Home for the Holidays is made possible by generous support from Joyce Chelberg.
White Rooster’s production sponsors include MAP Fund and Venturous Theatre Fund with Manilow Suites, production supporter.
Lookingglass Theatre’s 2025-2026 also season includes:
WORLD PREMIERE
March 5 - April 12
Written and Directed by Ensemble Member Matthew C. Yee
The Joan and Paul Theatre at Water Tower Water Works, 163 E. Pearson St. at Michigan Ave.
Opening Night is Saturday, March 14 at 6 p.m.
Tickets: $33 - $93
White Rooster is a darkly funny tale of love, loss and the strange things we inherit. After a family tragedy, Min is pulled into a world of restless spirits, old curses and mysterious traditions. Her fiancé won’t stay dead, her sister won’t stay buried and a rooster won’t be ignored. Blending spooky folklore with offbeat humor, White Rooster is a haunting tale of grief, family and the messiness of moving on.
WORLD PREMIERE
June 4 - July 12, 2026
Written by Ensemble Member Kevin Douglas
Directed by Devon DeMayo
The Joan and Paul Theatre at Water Tower Water Works, 163 E. Pearson St. at Michigan Ave.
Opening Night is Saturday, June 13 at 6 p.m.
Tickets: $33 - $93
Hilarity (and tragedy) ensue in the world premiere of Untitled Vampire Play when Val, a vampire, is in a new relationship with a mortal, Dom, each having different ideas about where their relationship should go. Rose, Val's progeny, wants Val to consider leaving the country, and on top of that, Val's estranged brother has returned, coincidentally, as a serial killer terrorizes the streets of Chicago. Untitled Vampire Play explores love, codependency, unwavering convictions and vampires.
Untitled Vampire Play features simulated violence, strong language, blood, sexual situations and suicide. It is recommended for audiences 14 and up.