He is renowned for his portrayal of swashbuckling heroes in such films as Captain Blood 1935, Robin Hood 1938, The Charge of the Light Brigade 1938, The Private Lives of Elizabeth and Essex 1939, The Sea Hawk 1940, and The Master of Ballantrae 1953. In The Sun Also Rises 1957 he portrayed a middle-aged Hemingway roue, and in Too Much Too Soon 1958 he portrayed actor John Barrymore. Flynn wrote an autobiography, My Wicked, Wicked Ways 1959. He became a US citizen 1942.