James Jackson, Jr. is an Obie Award-winning artist, educator, and actor, most recently recognized for his work in the Pulitzer Prize and TONY Award-winning musical A Strange Loop.

As a cabaret artist whose work has been seen across the country at Joe’s Pub, Williamstown Theatre Festival, Duane Park, 54 Below, American Repertory Theatre’s Club Oberon, Los Angeles’ Lyric Theatre, and The Green Room 42 with hit shows Shady Sings the Blues, I Just Wanted to Wear This, and The Black-Ups (with co-creators LaDonna Burns and Elliot Roth), James has also graced the prestigious stages of Radio City Music Hall and Carnegie Hall.

In addition to sold-out cabaret work with the Juneteenth Provincetown Committee, James has performed at The Provincetown Theatre, whose Board of Directors he joined in the Spring of 2025. He has also worked at The Post Office Cabaret, The Mary Heaton Vorse House, The Wilde, and Tin Pan Alley.

As an arts-educator, James has taught at Manhattanville University, University of South Florida (Tampa & Sarasota), Open Jar Institute, and his alma mater Westfield State University, where he was named 2024 Alumni of the Year and keynote speaker for the 2025 Sankofa Awards Ceremony presenting the inaugural James Jackson, Jr. Award for Resilience & Community Engagement.

James has also worked closely with Skyline Arts and The Youth Foundation of Jersey City. He is the co-creator of the Broadway-themed podcast “5 Questions with James & JAM” with TONY Award nominee John-Andrew Morrison,

Off-Broadway, James was last seen in White Girl in Danger (Second Stage/The Vineyard), with other stage credits including The Radio City Christmas Spectacular, Sir Andrew Lloyd Webber’s Whistle Down the Wind (National Tour), Dreamgirls (DASH Award), The Wild Party (SpeakEasy Stage), and Exigent Theatre’s gay re-invention Henri Gabler. Directing credits include Gypsy with College Light Opera Company.

James’ debut album, Birth, will be available summer 2025.