Max Roll and Harris Milgrim in Asolo Rep’s Good Night, Oscar. Photo by Adrian Van Stee.

Frontmezzjunkies presents: Asolo Rep’s Good Night Oscar Concludes Successful Run in Sarasota

An Interview conducted by Michael Raver 

Celebrities often play by different rules. They’re given permission to color outside the lines or they’re given opportunities that the rest of us can only dream of. In America, they’re the closest thing we’ve got to royalty. The downside is that those privileges can come at a cost. 

Good Night, Oscar is a retelling of an appearance made by the trouble-making musician and raconteur Oscar Levant on The Tonight Show. Effervescent and oozing charm, he fumbles to reconcile his public and private personas in the shadow of his haunting musical genius. For Levant, his fame is a carrot he can’t help but chase. Unfortunately, it also has him by the throat.

From left: Jonathan Acosta, Harris Milgrim, and Max Roll in Asolo Rep’s Good Night, Oscar. Photo by Adrian Van Stee.

Actor Max Roll understudied Sean Hayes when he originated the title role of in the original Broadway production. Now, the Yale Drama grad has made his way to Asolo Repertory Theatre’s stylish production of the Doug Wright play.  

I had an audition with the same casting office a couple of weeks prior, and they must have remembered me for this,” Roll says of his audition for the play. “’Very much a ‘You play the piano, yes?’ sort of thing. I went in to audition and met with Doug, Lisa, and the creatives, and clearly did something right.

Directed by Peter Amster, Good Night, Oscar closed out its successful run on April 28th, but not without leaving a vibrant impact on the city of Sarasota.

Max Roll and Jonathan Acosta in Asolo Rep’s Good Night, Oscar. Photo by Adrian Van Stee.

Given your previous experience with the piece, how does it feel to step into this role at the Asolo?

Doing this at the Asolo is my first real experience with the role. Stepping in for a performance on Broadway was a once-in-a-lifetime experience, but having the chance to explore the role fully here is so rewarding.

What has been the most challenging aspect of playing Oscar Levant?

Oscar is a slew of contradictions. His mental agility is remarkable, and to stay that level of alert and active is a big challenge. Combine that with the piano playing. And, well….it’s tough.

Was there something about Levant that surprised you this time around?

His generosity. His humor is biting, and he might often appear surly, but he’s generous with his attention.

How has it been working with Peter Amster?

Peter was a joy! He had his own ideas forged in years of experience and a deep understanding of comedy, music, and timing. Add to that a deep love of the play. I trusted him implicitly, and I think that trust went both ways. I felt so safe with Peter.

What do you hope audiences take away from the production?

I hope audiences leave feeling galvanized and curious about Oscar and the people around him. Being so brutally open and honest the way he was about his mental illness required a great deal of chutzpah and vulnerability. His wife, June, is the real hero of the play, though.

Sasha Andreev and Max Roll in Asolo Rep’s Good Night, Oscar. Photo by Adrian Van Stee.

For more information about Asolo Rep, visit https://www.asolorep.org/

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