Born the youngest of eight brothers and sisters in Ventura, California and raised in Oxnard, California, Henry's father was employed by the U.S. government as a commercial painter and is listed as a painter on Henry's birth certificate. At Oxnard College he took art classes under James Jarvaise who became an ongoing mentor. After ten years of working as a psychiatric technician at Camarillo State Mental Hospital he retired in 1997. He attended the California Institute for the Arts, where in 1995, he got his Bachelor's of Fine Art.
Taylor's largest output of work is in portraiture: he is known to paint obsessively, on various materials, including empty cigarette packs, detergent boxes, cereal boxes, suitcases, crates, bottles, furniture, and stretched canvas. His subjects include family, friends, patients (when employed at the hospital), acquaintances, strangers, waitresses, celebrities, homeless people, himself, and also historical figures, cultural figures, sports heroes, politicians, and individuals from photographs or other art works. Taylor's painterly style has been variously described as sensuous, vibrant, bold, fast and loose, full of empathy, generosity, and love, and the visual equivalent to blues music, while retaining a profound critical social sensibility. His work has been lauded for maintaining an impossible balance between careful and sophisticated art-world references with a seemingly spontaneous and natural expressiveness. Taylor's oeuvre has been aligned within various American lineages, including the portraiture tradition of Alice Neel, and the work of Harlem Renaissance painters such as Jacob Lawrence and Romare Bearden, and compared with his peer Kerry James Marshall.
Taylor's important exhibitions include a mid-career retrospective at MoMA PS1, along with solo exhibitions at the Studio Museum in Harlem, Artpace, and the Santa Monica Museum of Art, along with group exhibitions at the Whitney Museum of American Art, the Corcoran Gallery of Art, the Museum of Contemporary Art, Los Angeles, the Hammer Museum, the Carnegie Museum of Art, the Rubell Family Collection, and the Bruce High Quality Foundation. Taylor is represented by Blum & Poe Gallery in Los Angeles and Feur Mesler gallery in New York.
“I paint everyone, or I try to. I try to capture the moment I am with someone who could be my friend, a neighbor, a celebrity, or a homeless person.”
"It takes courage to do a lot of things. But, in a way, it doesn’t actually take courage, because you are free to do it. It’s like jumping in the water. The water’s cold, but you just jump in. You’ve gotta just jump in all the f****** time."