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Herbert Gentry was born in Pittsburgh in 1919 but relocated with his family while he was still a small child to Harlem, where he grew up. In his youth, Gentry was deeply influenced by his mother, a beauty contestant winner at the Savoy Ballroom and a dancer and showgirl. "I became conscious of the world through my mother, through the way I was entertained by her." (-Herbert Gentry, Oral history interview with Herbert Gentry, 1991 May 23, Archives of American Art, Smithsonian Institution.) He accompanied her to shows and museums, traveling and meeting her friends, many of whom were singers, dancers, directors, and writers. He would spend the rest of his life constantly moving around, meeting new people, and painting.

In junior high school, Gentry was first exposed to the arts when he was appointed the "class artist" by his teacher. He took art classes at the Y.M.C.A in Harlem, and at Roosevelt High School under the New Deal's W.P.A. Program, meeting many artists, mostly performing artists, writers, photographers, and musicians. Gentry began his life of travels as a child actor in the play Scarlet Sister Mary on the road with the theatre company. Later in his life, Gentry fought as a soldier in World War II when he traveled to North Africa, Corsica, Italy, Germany, Austria, and France- where he would return and further develop his art. In Paris, Gentry studied at the Academie de la Grande Chaumiere, opened a club-galerie in Montparnasse, and met many artists, including Richard Wright, Juliette Greco, Jean-Paul Sartre, Simone de Beauvoir, George Braques, and Romare Bearden. However, Gentry did not stay in Paris for long; in 1959 he was invited to exhibit in Copenhagen and settled there until 1964, when he moved to Gothenberg, and later Stockholm, Sweden, all the while keeping a studio in Paris. Gentry would rotate between the different international art worlds, actively participating in the art and jazz scenes there, eventually including New York as one of his bases. "I never felt that I was localized, that I had to stay in a certain area. That's why when I grew up and had my own life, I never stayed only on the block that I lived on. I would go somewhere else, meet other people." (-Herbert Gentry, Oral history interview with Herbert Gentry, 1991 May 23, Archives of American Art, Smithsonian Institution.)

Although Gentry may not be as well-known as some of his contemporaries, his influence on artists and musicians of his time spans continents. Because he spent so much time traveling, he never established a firm enough reputation in one place. He painted in a semi-figural abstract style, suggesting images of humans, masks, animals, and objects caught in a web of circular brushstrokes encompassed by flat, bright colors. He has suggested that his works are uncalculated- coming from his subconscious- painting what he feels as he feels it. Gentry's striking images are the product of his exposure to exotic people and places throughout his lifetime. "It's the magic that does the painting, and the magic is within. I can't see having substance without having magic in the painting. I use hands, fingers, I'll use anything at that point, it depends. ... I believe sometimes you use the thing nearest if it's possible. ... The main thing is to get that idea over quickly. Because that feeling, that thought is a very short thought, as an artist it doesn't last a long time. If you can get it down right away, work with it technically later on. For example, you see a form...should I... shouldn't I...PUT IT DOWN! Then technically, if it doesn't fit or you didn't do it right, you can work with it. But that feeling, that idea, that spiritual thing, you just put it down right then!" (-Herbert Gentry, Oral history interview with Herbert Gentry, 1991 May 23, Archives of American Art, Smithsonian Institution.)

Throughout his artistic career, Gentry has participated in many solo and group exhibitions. He has had solo exhibitions at Diggs Gallery, Winston-Salem State University, NC; G.R. N'Namdi Gallery, New York, NY, Chicago, IL, and Detroit and Birmingham, MI; Wadsworth Atheneum Museum of Art, Amistad Center for Art and Culture, Hartford, CT; Phillips Museum of Art, Franklin & Marshall College, Lancaster, PA; Stella Jones Gallery, New Orleans, LA; Alitash Kebede Gallery, LA, CA; Randall Gallery, New York, NY; Parish Gallery, Georgetown, DC; to name of few of his domestic shows.