Good Night, Oscar Review – An Uninspired Script

(L-R): Ben Rappaport and Sean Hayes in Doug Wright’s Good Night, Oscar
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Two questions I’ve carried with me from my days as an undergraduate theatre major to my current career as a theatre critic are “why now?” and “why this play?” They encourage me to think about the relevance of a specific show to the specific moment in which it’s being performed, which is essential for an art form so bound by time and space. In the case of Good Night, Oscar, written by Doug Wright and currently premiering at the Goodman Theatre, I am left without an answer to either question.

(L-R): Ben Rappaport, Sean Hayes and Peter Grosz in Doug Wright’s Good Night, Oscar

The stakes of the show are this: late-night host Jack Paar must prove that The Tonight Show can be successful if filmed in Los Angeles instead of New York. To do so, he’s invited pianist and comedian Oscar Levant as his opening guest. There’s a hitch, however, which is that Oscar is currently in an in-patient mental health facility; he is able to sneak out for four hours only by using a “pass” acquired by his wife. There’s lots of angst about Oscar’s mental illness, his relationship to George Gershwin, and the producer’s request that he avoid the topics of politics, religion, and sex while live on the air, and then the interview happens. That’s it. That’s the story.

(L-R): Emily Bergl and Sean Hayes in Doug Wright’s Good Night, Oscar

The stakes here are not exactly life-or-death. For the right character, it might be easy to root for the show’s success in its new home, but Jack isn’t particularly vividly drawn, and instead actor Ben Rappaport is left throwing plenty of charisma at a cardboard character it’s hard to care about. Indeed, it’s difficult to care much about any of the characters, from the one-dimensional producer Bob to the irritatingly enthusiastic assistant Max. Oscar himself is somewhat sympathetic, but that owes more to Sean Hayes’ powerful performance than anything to be found in the script. Overall, the script is lackluster, and it’s difficult to enjoy anything else, even the committed boldness of Hayes’ acting, when it all hangs on something so uninspired.

(L-R): Sean Hayes and Tramell Tillman in Doug Wright’s Good Night, Oscar

There is plenty of potential material to mine here—Oscar’s fear that he will always be stuck in Gershwin’s shadow, his mental illness, his wife’s struggle to care for him, the intersection of exploitation and entertainment—but none of those themes really blooms into anything full and meaningful. Instead, the play’s ending seems to suggest that the real takeaway here is something about what television ought to be, which is by far the least interesting element of the story. Perhaps if this script were used for prestige television instead of a live play, the reflection on the nature of televised entertainment would be more resonant. Much of the humor relies on an understanding of pop culture references from the 1950s, which went straight over my millennial head, rendering a play about a comedian much less funny than it should have been by rights.

(L-R): John Zdrojeski and Sean Hayes in Doug Wright’s Good Night, Oscar

Ultimately, I’m just not sure why this play needed to be produced now. If I were born fifty years earlier, maybe I would have at least found it entertaining or nostalgic, but at twenty-eight, in a world ravaged by climate change, war, disease, economic inequality, racial injustice, and countless other massive looming problems, it’s hard to imagine what Oscar Levant’s appearance on The Tonight Show in 1958 has to do with me or anyone else in current society. Despite the incredible talent at the show’s center, this one is a miss.

Ticket Information

Dates: March 12 – April 24, 2022

Location: Goodman Theatre, 170 N Dearborn Street, Chicago, IL 60601

Tickets: $25 – $112, subject to change. Available now at the Goodman Theatre’s website or by phone at 312.443.3800.

All photos by Liz Lauren.



  1. You actually touched exactly on the why now and why this play. You are too busy looking for bigger and more immediate and missing that the same thing happens with all the time now. Worse. Don’t let the fact the Levant was funny lead you away from the people we can’t look away from deteriorating before our eyes. And we keep poking and watching for reaction from them. We want to see them crash in front of our eyes. No one helps. They just watch. They use. And they watch some more.

  2. Yep, I agree with your review. I’m 63. I understood all the references. However, I too was left wondering why this story, why now? Sure it was entertaining, but the play itself was a bit vacuous. The audience loved it, so there’s that. I’ll look forward to reading your criticism, you appear to have some real insight into the theater and art. 🙌

  3. Jessie, you are sadly clueless. Why now? What’s at stake is freedom of speech, which is being chipped away at from all directions, media and otherwise. Why this play? It illuminates issues that have been relevant for seven decades and more. Anyway, Levant may be unknown to you twenty-somethings, but he was a genius you should know about

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