At the January 27 inaugural gala for Seriously Entertaining, a monthly “literary cabaret,” the actress Uma Thurman read three fiery passages as part of a literary quiz called “Tip of My Tongue.” The 380 audience members at the City Winery in downtown Manhattan were charged with identifying the titles and authors of the texts from which the passages were quoted, as well as the decade when each piece was originally published. Only one member of the very literary crowd nailed all three: Salman Rushdie.

Emcee Andy Borowitz, a New Yorker writer and author of the Borowitz Report, proclaimed Rushdie the victor and, throughout the night, introduced the event’s cast of performers who riffed, ruminated, and reflected on the night’s theme: “Plays with Matches.” New Yorker writer Adam Gopnik shared a story about delivering a somewhat improvised keynote address at a conference, while historian Simon Winchester scored with a comical and gory account of working as a mortuary assistant when he was a teenager. Susan Orlean, also of the New Yorker, pondered the city’s papaya chain phenomenon, and singer/songwriter Dar Williams closed out the evening with an acoustic set.

Seriously Entertaining is produced by nonprofit House of SpeakEasy, the brainchild of author Amanda Foreman and Lucas Wittmann, literary editor at the Daily Beast. Founded in 2013, House of SpeakEasy was born out of the pair’s partnership on a New York version of 5x15, the U.K.-based series of literary talks. House of SpeakEasy’s mission is manifold: to pioneer new ways of uniting writers with audiences; to recognize the economic value of content creation; and to promote innovative ways of bringing literature to communities in need of more ways to discover and buy books.

“I think that there has been a tectonic shift in the way people view and approach cultural and literary entertainment,” Foreman said. “You can plug into literature and books very easily, but it’s also meant that there’s a need for genuine, real, physical connection—going somewhere, and having that special alchemy of ideas and companionship.”

Seriously Entertaining will be held monthly (excluding July, August, and December) at the City Winery. While tickets to the sold-out inaugural gala ranged from $250 at the individual level to gala sponsorship packages, raising over $250,000 to fund House of SpeakEasy projects, tickets for subsequent events will be in the $25–$45 range.

At the outset of the gala, Borowitz remarked that while we are living in an era of free content, we are unfortunately “not living in an era of free food.” As part of its mission to reinforce the value of a writer’s work, House of SpeakEasy will give half of the money raised by ticket sales at each of the 2014 events to the participating authors, and their books will be available for sale at City Winery the night of the show. (The writers on stage for the gala show were paid 50% of the take on a full house on a standard show night). In addition, the books will be sold via the House of SpeakEasy Web site, fulfilled through IndieBound.

Seriously Entertaining is House of SpeakEasy’s flagship initiative, but the group has developed other programs as well—to “nurture the next generation” of writers and readers, as Foreman put it. Through a generous anonymous donation, the organization founded SpeakFreely, which allows teachers and students to attend the monthly literary showcases free of charge. A Writer in Every Classroom sends Seriously Entertaining writers to public middle schools and high schools in New York City. As with the events, the writers are paid for their time and efforts, receiving $1,000 for a day’s work in the initiative. “They’re the rainmakers who make everything else happen,” Foreman said. “We’re not in the exploitation business. If they would be willing to go into this school, we’ll pay them to do it.”

Now that Foreman has the initial round of funding in place after the gala, she’s turning her thoughts to establishing House of SpeakEasy pop-up bookstores in “underserved communities,” like the Bronx and East Harlem—areas that will be “receptive but also [have] needs.” Foreman wants to eventually roll out the pop-up stores nationally.

The next Seriously Entertaining show will take place on February 24, and will be hosted by Academy Award nominee Steve Coogan. The show will feature Tom Reiss, Susan Minot, Anton Sword, and Dana Vachon, all musing on the theme, “This Is Not a Man.”