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WIT 2025: Branden Jacobs-Jenkins and Sanaz Toossi in Conversation with Vinson Cunningham

Saturday, September 27, 2025

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1:00 pm Eastern

Shakespeare & Company, 70 Kemble Street, Lenox, Massachusetts

Headshot of Branden Jacobs-Jenkins and Sanaz Toossi

Every play opens a new door.

Two of the best plays on Broadway this year were Branden Jacobs-Jenkins’s Purpose and Sanaz Toossi’s English. While Purpose blends comedy and drama to tell the story of a Chicago family whose patriarch was a leader in the Civil Rights movement, English brings audiences into a classroom where Iranian adults grapple with how learning a new language alters their identities.

Both Jacobs-Jenkins and Toossi have been praised for creating perceptive and absorbing works that hold past, present, and future feelings in the same space. Join these two Pulitzer Prize-winning playwrights for a wide-ranging conversation on what drew them to theater writing in the first place, the connection between performance and history, how they approach universal themes like representation and displacement, and their close collaborations with ensemble casts. “The pleasure is being surprised by how the form comes toward you and goes away from you,” Jacobs-Jenkins has said. “Every amazing moment in playwriting is linked to a revelation in acting.”

For Toossi, the origins of English date to the travel ban imposed by the U.S. government in early 2017 that affected many Muslim countries. When the play opened on Broadway in early 2025, she told the audience, “I am the daughter of two immigrants. It’s why I wrote the show, and it’s been my artistic North Star—to write us with dignity. We’re here because we will dictate the terms of who we are, and we will draw the contours of our identity. We will express ourselves as tender and contradictory and fallible. I do not want to live in a world without story, without make-believe, where we don’t go on a stage and tell the truth about who we are.”

WIT Literary Festival livestreams are produced by CTSB with promotional support from The Nation.

About the Speakers

Branden Jacobs-Jenkins won the 2025 Pulitzer Prize and Tony Award for Best Play for Purpose, which ran on Broadway earlier this year. He has written the book for the musical Purple Rain, which will premiere in Minneapolis next month. His play Appropriate won the 2024 Tony Award for Best Revival, making him the first playwright since Tony Kushner and Terrence McNally to win a Tony Award in back-to-back years. Other theater credits include The Comeuppance (Signature Theatre), Girls (Yale Rep), Everybody (Signature Theatre), War (Yale Rep; Lincoln Center/LCT3), Gloria (Vineyard Theatre), An Octoroon (Obie Award; Soho Rep, Theatre for a New Audience), and Neighbors (The Public Theater). He serves as Vice President of the Dramatists Guild Council and on the Boards of Soho Rep, Park Avenue Armory, the Susan Smith Blackburn Prize, and the Dramatists Guild Foundation. His honors include the Windham Campbell Prize for Drama and the inaugural Tennessee Williams Award, as well as fellowships from USA Artists, the Guggenheim Foundation, and the MacArthur Foundation. He teaches at Yale.

Sanaz Toossi’s play English was awarded the 2023 Pulitzer Prize for Drama and ran on Broadway in 2025. English also won the Obie Award for Best New American Play and was nominated for numerous Tony Awards. Her first play, Wish You Were Here, premiered at Playwrights Horizons in 2022. She is currently under commission at Atlantic Theater Company, Roundabout Theatre Company, Williamstown Theatre Festival, Manhattan Theatre Club, and South Coast Repertory. She was the 2019 P73 Playwriting Fellow and is a recipient of the Steinberg Playwright Award, the Horton Foote Award, the Hull-Warriner Prize, and an Outer Critics Circle Award.

Vinson Cunningham joined The New Yorker as a staff writer in 2016. Since 2018, he has served as a critic for the magazine, writing about theatre, television, and more. He was a finalist for the Pulitzer Prize for criticism in 2024 and was awarded the George Jean Nathan Award for Dramatic Criticism for 2021-2022. He teaches at the Yale School of Art and Columbia University’s School of the Arts, and he is a co-host of Critics at Large, The New Yorker’s weekly podcast about culture and the arts. His début novel, Great Expectations, came out in 2024.

Join us this September in the beautiful Berkshire Hills of Massachusetts for the WIT Literary Festival—a celebration of writers, their work, and the vital role they play in society. By bringing writers and readers together for an unforgettable weekend of timely conversations, the WIT Literary Festival reflects the belief that a rich culture of free expression is essential to a thriving democracy.

Who are we? What do we believe? In what kind of country do we want to live?

Guided by this year’s theme, The Power of Words: Authors & Activism, the WIT Literary Festival welcomes audiences to explore these abiding questions with a distinguished group of speakers renowned for their artistic virtuosity, intellectual passion, moral seriousness, restless faith, and civic engagement.

WIT 2025: Featured Conversations

DateTimeSession
Thursday, September 255 p.m. ETM. Gessen and Michael S. Roth in conversation with Alia Malek
Friday, September 262:30 p.m. ETJames Lawler and Tim Weiner in conversation with Garrett M. Graff
Friday, September 265 p.m. ETCatherine Coleman Flowers and Peter Hotez in conversation with Jeremy S. Faust
Saturday, September 2710:30 a.m. ETTorrey Peters and Chase Strangio in conversation with Andrea Long Chu
Saturday, September 271 p.m. ETBranden Jacobs-Jenkins and Sanaz Toossi in conversation with Vinson Cunningham
Saturday, September 273:30 p.m. ETHanif Abdurraqib and Imani Perry in conversation with Shana L. Redmond
Sunday, September 2811 a.m. ETDavid W. Blight and Deval Patrick in conversation with Imani Perry
Sunday, September 283 p.m. ETBishop Mariann Edgar Budde and Marilynne Robinson in conversation with Paul Elie

Learn more about WIT 2025 here.