Upcoming Theatre

Wednesday, 20 May 2026 12:46

Chicago Shakespeare Theater announces As Long As You're Asking: A Conversation with Jason Alexander

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Chicago Shakespeare Theater (CST) announces the return of Jason Alexander for a special event, As Long As You're Asking: A Conversation with Jason Alexander. In this evening of comedy, musical performance, and conversation with the Emmy and Tony Award-winning star of stage and screen, the audience determines what they want to know the most. Alexander presents a variety of topics for the audience to pick and choose, culminating in behind-the-scenes stories of his life, career, and social activism. Or ask about anything you've always wanted to know and see if he can answer. It's all on the table and the conversation is completely in your control—making for a once-in-a-lifetime evening, June 25 & 26 only in The Yard.

About Jason Alexander

Though best known for his award-winning, nine-year stint as the now iconic George Costanza of television's Seinfeld, Jason Alexander has achieved international recognition for a career noted for its extraordinary diversity. Aside from his performances on stage, screen, and television, he has worked extensively as a writer, composer, director, producer, and acting teacher. In between all that he has also become an award-winning magician, a notorious poker player and a respected advocate on social and political issues. For his depiction of George on Seinfeld, Jason garnered six Emmy nominations, four Golden Globe nominations, an American Television Award, and two American Comedy Awards. He won two Screen Actor Guild Awards as the best actor in a television comedy despite playing a supporting role, and he was honored to receive the Julie Harris Award for Lifetime Achievement from the Actors Fund in 2012.

Aside from Seinfeld, Jason has starred and guested in such shows as The Marvelous Mrs. MaiselMad About YouThe GrinderDrunk HistoryFriends, Two and a Half MenThe New Adventures of Old ChristineCriminal MindsMonkFranklin and BashCurb Your EnthusiasmBob PattersonListen UpHit the RoadOrville and Young Sheldon. He also starred in the television films of Bye Bye BirdieCinderellaA Christmas Carol and The Man Who Saved Xmas. Additionally, his voice has been heard most notably in DuckmanThe Cleveland ShowAmerican DadTom and Jerry and Kody Kapow. He can also be heard in the animated series Harley Quinn. His many films include Electric StatePretty WomanJacob's Ladder, Love Valor CompassionRocky and BullwinkleDunston Checks InThe Hunchback of Notre Dame, and Shallow Hal. In addition, he directed the feature films For Better or Worse and Just Looking. He is also a distinguished television director, overseeing episodes of SeinfeldEverybody Hates ChrisMike and MollyCriminal MindsFranklin and Bash and Young Sheldon. He won the American Country Music Award for his direction of Brad Paisley's video "Cooler Online."

While still in college, Alexander's desire to work as a stage actor in New York came to be with his debut in the original Broadway cast of the Hal Prince and Stephen Sondheim musical Merrily We Roll Along. He continued starring on Broadway in the original casts of Kander and Ebb's The Rink, Neil Simon's Broadway Bound, Rupert Holmes' Accomplice and his Tony Award-winning performance in Jerome Robbins' Broadway. He also authored the libretto for that show, which went on to win the Tony Award for Best Musical. After moving to LA, Jason continued working in the theater, notably serving as the artistic director for the Reprise Theatre Company and for the hit West Coast production of Mel Brooks' The Producers, in which he starred alongside Martin Short. Alexander returned to Broadway to star in the Larry David comedy Fish in the Dark at the Cort Theater and in John Patrick Shanley's The Portuguese Kid at Manhattan Theatre Club. He also starred in the world premiere of Rob Ulin's Judgment Day at Chicago Shakespeare Theater.

He also helmed a number of stage productions including: The God of Hell at the Geffen Playhouse; Broadway Bound at the Odyssey; an updated revival of Damn Yankees and The Fantasticks, as well as Sunday in the Park with George for Reprise; the world premiere of Windfall by Scooter Pietsch for the Arkansas Repertory Theater; Native Gardens at the Pasadena Playhouse; The Joy Wheel at The Ruskin Group Theatre; If I Forget at the Fountain Theater; and The Last Five Years at Syracuse Stage. He directed Sandy Rustin's The Cottage on Boradway in 2023 and is set to direct the film version in 2026. Earlier this year, Alexander directed an exciting, newly conceived production of Sondheim's Sweeney Todd for La Mirada Theatre, along with the world premiere of Scooter Pietsch's new play Fault at Chicago Shakespeare Theater. Alexander also hosts a weekly podcast, Really No Really, with Peter Tilden.

More information at chicagoshakes.com/jason-alexander or on social media at @chicagoshakes.

 

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