Flynn co-starred with Olivia de Havilland a total of eight times , and together they made the most successful on-screen romantic partnership in Hollywood in the late 1930s-early '40s in Captain Blood ( 1935 ) , The Charge of the Light Brigade ( 1936 ) , The Adventures of Robin Hood ( 1938 ) , Four 's a Crowd ( 1938 ) , Dodge City ( 1939 ) , The Private Lives of Elizabeth and Essex ( 1939 ) , Santa Fe Trail ( 1940 ) , and They Died with Their Boots On ( 1941 ) .
They appeared together in eight movies : Captain Blood ( 1935 , his first great success ) , The Charge of the Light Brigade ( 1936 ) , The Adventures of Robin Hood ( 1938 ) , Four 's a Crowd ( 1938 ) , Dodge City ( 1939 ) , The Private Lives of Elizabeth and Essex ( 1939 ) , Santa Fe Trail ( 1940 ) , and They Died with Their Boots On ( 1941 ) .