Herbert Gentry (July 17, 1919 in Pittsburgh, Pennsylvania - September 8, 2003 Stockholm, Sweden) was an expressionist painter and product of the Harlem Renaissance. Gentry's paintings juxtapose faces and masks, shifting orientations of figures and heads—human and animal—into profiles, to the left, to the right, above and below. The direction of the head, as face or profile, leading right or left, or facing front, is played against the relative scale of each head, its position on the canvas, and in relationship to the others.

The faces evoke subtle expressions and moods. Rather than using images to depict a concrete story, Gentry releases his experiences upon the canvas. The act of spontaneous painting uses consciousness itself, and each painting reveals the self. When asked about direct influences, he avoids imposing external meanings upon primary experience, describing instead his creative process. Romare Bearden (1981) wrote that Gentry's "method is conceptual rather than realistic. One senses in the chromatic emotionalism, and in the biomorphic forms of the figures that often appear in Gentry's paintings, the strong pull of the unconscious.” Philosophically near the jazz musician, Gentry breathes rhythms into a personally inflected expressionism. Gentry creates a foil for feelings and for emotion, and orchestrates his subjective figuration in dialogue with the immediacy of the painted gesture.

Educated in the New York City public schools, Gentry attended Cooper Junior High and George Washington High School. He pursued drawing in school, took art classes at the Harlem YMCA, and later studied art as part of the Federal Art Project of the WPA (Works Progress Administration) at Roosevelt High School.

He served in the U.S. Army in World War II, which took him to different countries in the Mediterranean and Northern Europe: Morocco and Algeria. At the war's end, Gentry was stationed in a Paris suburb. He took every opportunity to visit Paris.

He lived and worked in Paris, France (1946–70; 1976–80), Copenhagen, Denmark (1958–63), in the Swedish cities of Gothenburg (1963–65), Stockholm (1965–76; 2001–03), and Malmö (1980–2001), and in New York City (1970–2000) as a permanent resident of the Hotel Chelsea.

Important retrospective exhibitions since the artist's death include: "Herbert Gentry: Moved by Music," Wadsworth Atheneum, Amistad Center for Art and Culture, Hartford, Connecticut, 2006; "Herbert Gentry: the Man the Magic, the Master," James E. Lewis Museum at Morgan State University in Baltimore, Maryland, 2007; "Herbert Gentry: the Man the Magic, the Master," Diggs Gallery, Winston-Salem State University, North Carolina, 2008; "Herbert Gentry: Facing Other Ways," Rush Rhees Library Rare Books and Special Collections, University of Rochester, Rochester, New York, 2007; "Face to Face," Phillips Museum of Art, Franklin & Marshall College, Lancaster, Pennsylvania, 2005.