The Radical Self-Awareness of Michael R. Jackson

He's become one of the most surprising and incisive-and misunderstood-social critics of our time.

-  Thomas Chatterton Williams

In the summer of 2020, the playwright Michael R. Jackson received an unusual message from a fan of A Strange Loop, his musical about a gay Black man’s path to creative self-awareness through the process of writing a musical about a gay Black man’s path to creative self-awareness. “Can I buy you a bulletproof vest?” the fan inquired over Instagram.

Jackson, who had just won a Pulitzer Prize for A Strange Loop and lived on a perfectly safe street in Upper Manhattan, had no more conceivable use for body armor or handouts than the next man. He told me about the proposal several months ago, over steak frites at Soho House, stressing its absurdity and presumptuousness. “Ur life matters so much. Ur writing matters so much. This is the most available and direct way I can think of protecting ur life and ur future plays,” the fan had explained.

In person, Jackson at first seems unassuming and even shy. He does not reflexively generate small talk. But he responds candidly and at length when asked a question about almost anything, and he is wickedly funny. In Jackson’s diagnosis, the fan in question was haplessly inspired by the racial reckoning then gripping the nation; he felt compelled to “show up” in the name of white allyship and antiracism. Jackson compromised with his would-be savior: For the benefit of the latter’s conscience, he’d accept the vest’s cash value of $400. The man promptly sent this sum to Jackson via Venmo.

This bizarre exchange was emblematic of an entire constellation of assumptions, biases, and misunderstandings that has proliferated in recent years and altered the way Jackson thinks of himself, his work, and American society more broadly. “Once the pandemic and the protest began, I suddenly was like, Oh