In 1919, he interrupted his studies in the Fine Arts School of Porto (Escola Superior de Belas Artes do Porto), and resumed his education in Paris, where Cormon and Bérard were among his teachers.
He lived in London for ten years, before arriving in Rome, where he painted Mussolini's portrait. He traveled to São Paulo, Buenos Aires, Madrid, came back to Paris and traveled to Stockholm. He eventually moved to the US. He lived in Hollywood, California for six years and painted actresses' portraits, and the painting of Dorian Gray in the MGM film The Picture of Dorian Gray (1945).
In his youth, Medina had spent vacations in his family's house in the suburbs of Marinhas, located in the municipality of Esposende. In 1974, at the age of 73 he returned to Esposende to live, and to paint portraits of rural life. Today, the secondary school of Esposende is named "Escola Secundária Henrique Medina" (Secondary School Henrique Medina) in his honour.
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