Review: Strong Performances Elevate Matt & Ben at Jarvis Square Theater

Though their earliest acting credits date back to the 1980s, it’s hard to argue that 1997 wasn’t the true launch of Matt Damon’s and Ben Affleck’s careers. Both featured in Kevin Smith’s Chasing Amy, but their real triumph that year was Good Will Hunting. Conceived several years earlier as an assignment for Damon’s playwriting class, the eventual film saw the pair sharing a screen with no less than Robin Williams and earning an Oscar for Best Original Screenplay.

It’s tempting to wonder how two novice writers could achieve that level of success without the help of some higher power, and that’s the premise of Matt & Ben. Written in 2001 by Dartmouth classmates Brenda Withers and soon-to-be star of The Office Mindy Kaling, the play depicts Damon and Affleck as friends with big ambitions struggling to adapt The Catcher in the Rye as a script. When the screenplay for Good Will Hunting literally falls from the sky into their apartment, they’re unsure how to handle this lucky break.

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Kendal Romero and Connar Brown Sprenger in Matt & Ben. Photo credit: Tyler Core.

Directed by Tony Lawry, Theater Above the Law’s new production of Matt & Ben at Jarvis Square Theater continues in the tradition of Withers and Kaling, with female actors Connar Brown Sprenger and Kendal Romero portraying the titular Boston buddies. There’s a fun twist here, however—before each performance, the audience votes on which actor will play which Good Will Hunting scribe. When I saw the show, Sprenger portrayed Damon and Romero was Affleck, but based on their excellent performances, I have no doubt that audiences are in for a good time regardless of who’s playing who. Though I imagine the manic, slow-witted Affleck would be the more fun role, both actors performed their roles with full commitment, gusto, and precision.

The entire show takes place in their apartment, which is decorated to frat boy perfection: prominent groceries include Chips Ahoy and cereal boxes, and a Patriots emblem above the door earns a lucky tap from Affleck any time he exits. There's more litter surrounding a trash can than inside of it, though Romero uses it to great effect with an impressive bank shot off the wall into the trash can from an angle that would make a pool hall hustler envious. The two actors are the centerpiece of the show, but Gwyneth Paltrow and JD Salinger pop in for fantasy sequence cameos (whoever plays Affleck will also portray Paltrow, while Damon doubles up as Salinger).

Though the performances and production were top-notch, I expected the book to deliver bigger laughs. Perhaps the grounded approach is a better direction in light of the show’s inherently silly premise, but the novelty can only last so long before it begins to feel directionless and repetitive. That it takes place essentially in real time in a single setting is a wise creative decision, but also a limiting one. 

That said, the dialogue is tight and quippy, and the recurring jokes are peppered in strategically to avoid predictability and remain rewarding. The highlight was a flashback to a high school talent show where the duo were at odds over a performance of “Bridge Over Troubled Water.” It was a much-needed departure from the battle over the Good Will Hunting script—although that too paid off thanks to Lexi Dewitt’s impeccable fight choreography.

Kendal Romero and Connar Brown Sprenger in Matt & Ben. Photo credit: Tyler Core.

Though the script wasn’t the laugh riot I was hoping for from a Mindy Kaling project, Sprenger and Romero make this production of Matt & Ben entirely worthwhile. I’d love to see them team up again in the future—that both actors are prepared to tackle either of the title roles at a moment’s notice is a testament to their talent. Maybe in a few years, we’ll be lucky enough to see Damon and Affleck return the favor in Connar & Kendal.

Matt & Ben runs Fridays and Saturdays at 7:30pm and Sundays at 3pm through June 29 at Jarvis Square Theater. Running time is 70 minutes. Tickets ($25) are on sale now.

For more information on this and other productions, see theatreinchicago.com.

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Anthony Cusumano

Anthony Cusumano is a comedy writer, performer, and producer based in Chicago. In 2023, he launched The DnA Sketch Show, a recurring variety show, and in 2024 he wrote and directed the critically acclaimed musical Miracle at Century High School.