On the day that war broke out in the Middle East, a box of 70 tote bags arrived at my house, each adorned with Anne Frank’s face.

This was not a hate crime. The totes were meant to be gift bags at an upcoming screening of my short film, a dark comedy that imagines a meeting between the Anne Frank House and the New York design firm they’ve hired to help them renovate the gift shop to appeal to young people. “The Anne Frank Gift Shop”—which stars Ari Graynor of HBO’s Winning Time and Abbott Elementary’s Chris Perfetti—asks the question: Is there a wrong way to talk about the Holocaust? I’d argue no. But is there a wrong time?

“The Anne Frank Gift Shop” is a dark comedy that imagines the Anne Frank House’s attempt to appeal to young people.

It’s a strange moment everywhere, including Hollywood, as a slew of filmmakers (myself included) try to figure out how to talk about their Holocaust projects amid a devastating war that’s only reminded the world what’s at stake. Jonathan Glazer’s The Zone of Interest (opening December 15 after a six-minute standing ovation at Cannes) concerns the mundane life of an S.S. officer and his wife who live next door to Auschwitz. Steve McQueen’s Occupied City is a deliberately paced, four-hour documentary about Amsterdam in World War II. (It opens on Christmas Day.)

Elsewhere, the creators of the National Geographic limited series A Small Light, about Miep Gies—who helped conceal Otto Frank and his family in the “Secret Annex” of an Amsterdam office building for two years—are on the campaign trail, hoping to land SAG and Golden Globe nominations. (The series was just nominated for a Gotham Award, as was its star, Bel Powley.) “We’re promoting the show, and we’re being asked about the timeliness of it and how we feel,” says co-creator Joan Rater. “We feel terrible. We feel sick.

The National Geographic mini-series A Small Light tells the story of Miep Gies, who helped conceal Otto Frank and his family.

It’s a bizarre question to ask an artist. Does a film about the Holocaust really need a news peg? After winning the top prize at the San Francisco Jewish Film Festival in June, “The Anne Frank Gift Shop” is streaming for Oscar voters on the Academy Web site. I recently flew to Savannah for a screening and Q&A at the SCAD Savannah Film Festival, where I happened to catch The Zone of Interest, followed by a talkback with the German actor Christian Friedel.

Is there a wrong way to talk about the Holocaust? I’d argue no. But is there a wrong time?

Seated on a handsome stool, Friedel talked about the emotional toll that comes with playing an S.S. officer, saying he was “still processing” the character’s darkness “out of my body and my soul.” Which is surely true. But all I could think about was his sharp, black suit and gray turtleneck. Or, more specifically, how he and a stylist had likely met to plan a series of press-tour looks for a film that includes a garden party in earshot of a crematorium. Hopefully the suit wasn’t Hugo Boss.

Jonathan Glazer’s The Zone of Interest follows an S.S. officer and his wife who live next door to Auschwitz.

Boss is a German brand. And if you laughed at that you might enjoy “The Anne Frank Gift Shop.” In the midst of a heated pitch meeting at the design firm’s office, one character refers to Miep Gies as “the original Uber Eats.” Another—a Gen Z influencer—reveals she’d recently visited the infamous attic and reports it’s “huge.” The film is produced in part by Jane Sinisi, the granddaughter of Holocaust survivors, and the first person to tell me it was O.K. to put an escape-room joke in a movie about Anne Frank. How else do we process horror?

My film was inspired by a landmark 2020 study by the Conference on Jewish Material Claims Against Germany, which revealed that a majority of young Americans did not know basic facts about the Holocaust. Two-thirds of those surveyed apparently could not tell you that six million Jews were murdered; 11 percent somehow believe Jews “caused” it.

Steve McQueen’s four-hour documentary, Occupied City, explores the goings-on in Amsterdam during World War II.

How was that message getting lost? This was not ancient history. If Anne Frank were alive today, she’d be three years younger than Mel Brooks. And he had a show on Hulu last year. Anne Frank could have watched The Wizard of Oz on her 11th birthday, and it’s streaming on the Delta in-flight-entertainment app. We’ve always said, “Never again.” But here we were. Or as the comedian Alex Edelman half-joked on Instagram this week: “Everybody should be coming up with a gentile name” in case “things get really bad.”

“This is going to feel weird,” says Rater, who co-created A Small Light with Tony Phelan. “But we wanted to make the story … ‘entertaining’ is the wrong word. Let’s go with compelling. Miep’s relationship with Jan”—their meet-cute—“makes the story human and relatable. You want to watch it. And in watching it you’re also learning shit.” She added, “Holocaust education is proven to reduce anti-Semitism. It’s only mandated in, I think, 27 states.” It’s actually 23. But who’s counting?

I’d thought about canceling that event in Los Angeles—the one I’d ordered all of those Anne Frank tote bags for. But canceling felt performative. Like reposting some 12-slide thread from the third lead on Riverdale.

The film The Diary of Anne Frank was based on the Pulitzer Prize–winning play of the same name.

“The Anne Frank Gift Shop” aims to meet Gen Z where they live, disarming them with a comedic language they speak before hitting them with the film’s essential appeal—which is something I said a dozen times on a press line in Savannah while a publicist held my phone (so as not to wrinkle my pants in photos). As one character says, “We have to keep telling this story again and again and again—every which way we can—or it will happen again.” Which doesn’t fit on a tote bag but is unfortunately true.

By the way, I eventually sent the film to the team at the actual Anne Frank House in Amsterdam, who’d read about it online and were “intrigued.” Three days of silence followed. Finally, an e-mail arrived. The head of communications wrote to say the film “ticks all the right boxes,” acknowledging our shared purpose: “It is also a challenge for us to reach Gen Z.”

She did, however, have one suggestion. The film, she said, should be properly subtitled. The automatically generated captions were apparently poor in places. Which I guess means she and her staff wanted to properly hear each Holocaust joke. As for what they did make out, she said, “We had a good laugh.”

Mickey Rapkin is a journalist and screenwriter whose first book, Pitch Perfect, inspired the film series about a cappella singing. Rapkin was previously a senior editor at GQ; “The Anne Frank Gift Shop” marks his directorial debut