By DORIS RUBENSTEIN
John Orenstein was one slick attorney for many years. He knew how to get what he wanted for his clients and still knows how to get what he wants for himself. Most wannabe Fringe Festival performers play at “purim” when it comes to being selected to present their play, their dance, their magic tricks, their “whatever” that makes a Fringe Festival a Fringe Festival: Selections are made through a lottery.

Maybe because he isn’t a starving artist, Orenstein can skirt the slim chance of getting his plays into the Fringe by paying a fee as an “independent producer.” He did it in 2023 with Extreme Roadshow, a singing and dancing comedic take on Antiques Roadshow. Now, he’s the creative force behind Make America Gray Again!, a musical comedy.
Orenstein did it all up to production: He wrote the book and lyrics and composed the music. The plot follows the protagonist, Dan, as he looks for purpose in his (forced) retirement. Advised by a talking book, he encounters corporate America, the Heritage Foundation, militant baby boomers, God and the meaning of life. Also, he dies.
By the way, Dan is not Jewish, but God definitely is!
Orenstein was inspired to create this play as a result of his four years of participation and leadership in the senior lawyers section of the Minnesota Bar Association. It’s not a very exclusive group; all you need to belong is to have survived to age 62 or beyond. Lawyers participating in the section learn how to deal with the stress of transitioning to retirement after years of living with the law.
The programs suggest all kinds of activities but also raise the existential question of “Who am I beyond my profession?” He tried to remain apolitical with the play, but his attempt was thwarted by the ubiquitous political atmosphere of our time, hence the play on words in the musical’s title.
It took an intense nine months of creative activity to give birth to Make America Gray Again!
“I think that any time you write a play, you end up writing about your obsession of the moment,” he commented.
Judaism sneaks into the play as well, since it’s a big part of Orenstein’s life. Along with his wife Debbie, he has created various cabaret acts and dozens of Purim shpiels at Beth El Synagogue. He’s now added Shir Tikvah to his Jewish affiliations, attracted by the musical nature of much of the prayer service there.
Orenstein is not acting in the play, but he plays the piano throughout. And while none of the actors are Jewish, the director is one of the Twin Cities’ most honored and talented Jews: Barbara Wiener.
Wiener’s career in film and television and teaching has spanned over 30 years. She was senior and executive producer at Twin Cities Public Television for 14 years, and she has made independent feature documentaries among other activities. Her arts and cultural documentary and performance work has received many awards, including six Midwest Emmys. Her work been seen in broadcast and screenings around the world, including the Walker Art Center’s Women with Vision, the New York International Film Festival, Chicago Silver Screen Film Festival, Women in the Director’s Chair, and the Sundance Film Festival.
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Make America Gray Again!, a show in the upcoming Minnesota Fringe Festival (minnesotafringe.org), will be performed 7 p.m. Saturday, Aug. 2; 4 p.m. Sunday, Aug. 3; 7 p.m. Tuesday, Aug. 5; 7 p.m. Thursday, Aug. 7; and 8:30 p.m. Saturday, Aug. 9, at Phoenix Theater, 2605 Hennepin Ave., Minneapolis. Tickets are available online where you can pay electronically. But if you pay cash at the door, the price is substantially reduced.
(American Jewish World, July 2025)