As Long As You’re Asking: An Evening with Jason Alexander

Featuring Jason Alexander

The Yard

Run Time: 90 minutes (no intermission)

An evening of comedy, musical performance, and conversation with the Emmy and Tony award-winning star of stage and screen in which 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. Alexander has starred on Broadway, in hit films like Pretty Woman, and, of course, Seinfeld. He is an actor, director, producer, writer, children’s book author, award-winning magician, semi-pro poker player, and social/political activist. It’s all on the table and the conversation is completely in your control—making for a once-in-a-lifetime evening at Chicago Shakespeare Theater.

Run Time: 90 minutes (no intermission)

Seat Map

FEATURING

MEET 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 teacher of acting. 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 in 2012 he was honored to receive the “Julie Harris Award for Lifetime Achievement” from the Actor’s Fund.

Aside from Seinfeld, Jason has starred and guested in such shows as The Marvelous Mrs. Maisel, Mad About You, The Grinder, Drunk History, Friends, Two and a Half Men, The New Adventures of Old Christine, Criminal Minds, Monk, Franklin and Bash, Curb Your Enthusiasm, Bob Patterson, Listen Up, Hit the Road, Orville and Young Sheldon. He also starred in the television films of Bye Bye Birdie, Cinderella, A Christmas Carol and The Man Who Saved Xmas. Additionally, his voice has been heard most notably in Duckman, The Cleveland Show, American Dad, Tom and Jerry and Kody Kapow. He can also be heard in the animated series Harley Quinn.

His many films include: Electric State, Pretty Woman, Jacob’s Ladder, Love Valor Compassion, Rocky and Bullwinkle, Dunston Checks In, The 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 Seinfeld, Everybody Hates Chris, Mike and Molly, Criminal Minds, Franklin 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, his 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/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 Robbin’s Broadway. Jason 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 along with Martin Short. Jason 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 Robert Ulin’s Judgment Day at the 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 directed the musical The Last Five Years at Syracuse Stage. For Broadway, he directed Sandy Rustin’s The Cottage at the Helen Hayes Theatre in July 2023 and is set to direct the film version in 2026. In January of 2026, Jason directed an exciting, newly conceived production of Sondheim’s Sweeney Todd for La Mirada Theatre to much acclaim. Jason is directing the world premiere of Scooter Pietsch’s new play Fault at Chicago Shakespeare Theater in spring of 2026. Jason’s weekly podcast, Really No Really, co-hosted with friend Peter Tilden is an attempt to find answers to the things that make us scratch our heads and ask, “how can that be true/real/possible?” Mr. Alexander tours the country and the world performing his one-man show, “As Long As You’re Asking, a Conversation with Jason Alexander,” which contains music, comedy and conversation. He can also be seen in his whimsical salute to Broadway musicals with some of the finest symphony orchestras throughout the United States.