Although he hadn't really planned on an acting career, Flynn become a star with his very first film, Captain Blood, in 1935. He was typecast as a swashbuckler and made several including The Adventures of Robin Hood (1938), The Sea Hawk (1940), (like Captain Blood, based on a novel by Rafael Sabatini), and The Adventures of Don Juan (1949). He also played opposite Olivia de Havilland in the western movie Dodge City (1939).
During the shooting of The Private Lives of Elizabeth and Essex (1939), Flynn and co-star Bette Davis had some legendary off-screen fights. His reputation as a womanizer led to the expression "In like Flynn." He was well known for having wild parties and eventually his own reputation had him brought up on a statutory rape charge in 1942 by teenagers Betsy Hansen and Peggy Satterlee. A group organized to support Flynn called the American Boys Club for the Defense of Errol Flynn (ABCDEF); among its members included William F. Buckley, Jr. The trial took place in January and February of 1943, and Flynn was cleared of the crime, but he suffered both personally and in his career.
By the mid 1950s, he was something of a self-parody but still won some acclaim as a drunken ne'er-do-well in The Sun Also Rises (1957). His autobiography, My Wicked, Wicked Ways, was published just months after his death from heart attack and contains humorous anecdotes about Hollywood. Flynn wanted to call the book In Like Me, but his publishers refused.
Flynn was married three times, to actress Lily Damita from 1935 until 1942 (one son, Sean); to Nora Eddington (1924 - 2001) from 1943 until 1948 (two daughters, Deirdre and Rory); and to actress Patrice Wymore from 1950 until his death (one daughter, Arnella Roma). His only son, Sean Flynn, became an actor and later a war correspondent who disappeared in Cambodia in 1970 during the Vietnam Conflict. The younger Flynn's life was recounted in "Inherited Risk" by Jeffrey Meyers (Simon & Schuster).
One of Errol Flynn's grandsons, sometime model Luke Flynn (ne Luke Stoecker, born 1976), the only child of Arnella Flynn (1953 - 1998) and fashion photographer Carl Stoecker, was named one of the world's sexiest bachelors by People magazine in 2003. His mother, a former fashion model, died on the Flynn family estate in Jamaica after a hard life of alcohol and drug addiction.