In Hollywood, Flynn spun his wheels in "The Case of the Curious Bride" and "Don't Bet on Blondes" (both 1935), before Warner Brothers made him a leading adventure star and roguish male sex symbol, often appearing opposite Olivia de Havilland in such classics as "Captain Blood" (1935), "The Charge of the Light Brigade" (1936), "The Prince and the Pauper" (1937), "The Adventures of Robin Hood" (1938) and "The Private Lives of Elizabeth and Essex" (1939). Flynn showed an unexpected flair for screwball comedy in the delightful "The Perfect Specimen" (1937).

As notorious for his dissipated lifestyle (drinking, drugs, sex, brawling) as for his dashing movie roles, Flynn was at the center of a controversy in 1942 when he was tried (unsuccessfully) for the statutory rape of two teenage girls. Amazingly, the scandal did not dent his popularity, and even spawned the still-current slang phrase "In Like Flynn". His career continued unabated through the 40s, with highlights including "The Sea Hawk" (1940), "They Died with Their Boots On" (1941), "Gentleman Jim" (1942) and "Objective Burma" (1945). His career and physical appearance went into decline, largely due to alcohol and drug abuse, in the late 40s, though he salvaged a battered critical reputation with roles as middle-aged drunkards in the 50s (in "The Sun Also Rises", 1957, and as John Barrymore in "Too Much, Too Soon", 1958). In mid-decade, he had some success with the British-made episodic "Errol Flynn Theater" on television. His autobiography, "My Wicked, Wicked Ways", was published posthumously in 1959; Flynn died of a heart attack at the age of 50.