WESTPORT, CONN.: The 2008 death of David Foster Wallace—the author of such works as the monumental novel Infinite Jest—left playwright Carly Mensch mourning the premature extinguishing of a bright literary light. She credits Wallace’s work as an inspiration for her new play Oblivion.

According to Mensch, “A lot of his writing is about this moral quandary: How do we figure out what moral values are endorsable in a morally relative universe? How do you be a good person despite the rapidly changing, technologically obsessed 21st-century world we live in?”

The testing of seemingly solid worldviews by life’s chaotic surprises lies at the heart of Oblivion, which plays at Connecticut’s Westport Country Playhouse Aug. 20–Sept. 7. The play revolves around a pair of “laid-back” Brooklyn parents whose 16-year-old daughter refuses to reveal where she spent the weekend after claiming to be on a college recruiting trip. When the truth comes out, the couple’s ethos of progressive acceptance begins to splinter.

Mensch’s adoration for Wallace is refracted in the text itself. Film critic Pauline Kael becomes a figure of obsession for the daughter’s friend, a teenage film geek who writes letters to the revered writer without realizing that she is deceased. By inserting Kael into the play, Mensch saw an opportunity to explore the little-discussed relationship between artists and critics, as well as to honor another writer she admires.

“I just love how fun and conversational Kael’s writing was,” Mensch said. “She didn’t feel like a critic; she felt like your best friend gushing over actors with you. And yet at the same time, she was wickedly smart and tapping into big ideas, writing with this zoomed-out perspective.”

The influence of both Wallace and Kael on the playwright shines through in Oblivion’s joining of messy emotion, intellectual heft, and idiosyncratic verbal wit. According to director Mark Brokaw, Mensch is “one of those people who can combine great humor with great gravity.”