James Jackson, Jr. is an Obie Award–winning performer and proud board member of the Provincetown Theater. A dynamic presence on and off the stage, James brings his passion for bold storytelling, equity, and community engagement to his work with the Theater. Best known for his role in the Pulitzer Prize and Tony Award–winning musical A Strange Loop, James is also a celebrated cabaret artist with performances across the country, including Joe’s Pub, 54 Below, Williamstown Theatre Festival, Club Oberon, and Carnegie Hall. In Provincetown, he’s performed at The Provincetown Theater, Post Office Cabaret, The Wilde, and with the Juneteenth Provincetown Committee. As an arts educator, James has taught at Westfield State University (his alma mater), Manhattanville University, and the University of South Florida. His stage credits include White Girl in Danger, Dreamgirls, The Wild Party, and Whistle Down the Wind. His debut album, Birth, is set for release in summer 2025.