ANTHONY RAPP: HOME FOR THE HOLIDAY is Coming to Lookingglass Theatre Company
Rapp is perhaps best known for starring as as Mark in the original Broadway cast of Rent.
By: Chloe Rabinowitz Nov. 17, 2025
Lookingglass Theatre Company will present 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.
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.
Lookingglass Presents
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.
Lookingglass Young Ensemble presents
EMMA
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.
On the Mainstage in 2026:
WORLD PREMIERE
WHITE ROOSTER
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
UNTITLED VAMPIRE PLAY
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.
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).
Chicago Awards - Live Stats
Best Musical - Top 3
1.
HAIRSPRAY (Uptown Music Theater of Highland Park)
7.4% of votes
2.
RENT (Highland Park Players)
7.4% of votes
3.
THE WIZARD OF OZ (Up and Coming Theatre/Elgin Summer Theater)
6.7% of votes
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