His writings on digital media and photography have appeared in Bomb, NKA Journal of Contemporary African-American Art, TRANS, Black Film Review, Felix, International Documentary Association Magazine and FUSE: Journal of Arts & Culture, where he served as contributing editor. Reggie's multimedia work has been featured at The Photographer's Gallery, London, the 40th Flaherty Film Seminar, and at MIT in Race in Digital Space. He has been an artist fellow at the Society of Humanities at Cornell University, Banff Centre for the Arts, and a critical studies fellow at the Whitney Museum of American Art's Independent Study Program. Woolery's received project support from Art Matters, New York State Arts Council, New York Foundation for the Arts, National Black Programming Consortium, and ITVS, among others. He has degrees from Parsons School of Design and New York University's Interactive Telecommunications Program of Tisch School of the Arts.