Flynn developed a reputation for womanizing, hard drinking, chain smoking and narcotics abuse. He was linked romantically with Lupe Vélez, Marlene Dietrich and Dolores del Río, among many others. He was a regular of William Randolph Hearst’s equally lavish affairs at Hearst Castle, though he was once asked to leave after becoming excessively intoxicated.
Flynn was married three times: to actress Lili Damita from 1935 until 1942 (one son, Sean Flynn, 1941 – c. June 1971); to Nora Eddington from 1943 to 1949 (two daughters, Deirdre, born 1945, and Rory, born 1947); and to actress Patrice Wymore from 1950 until his death (one daughter, Arnella Roma, 1953–1998).
While Flynn acknowledged his personal attraction to Olivia de Havilland, assertions that they were romantically involved during the filming of Robin Hood were denied by de Havilland.
Yes, we did fall in love and I believe that this is evident in the screen chemistry between us. But his circumstances [marriage to Damita] at the time prevented the relationship going further. I have not talked about it a great deal but the relationship was not consummated. Chemistry was there though. It was there.
By 1959, Flynn‘s financial difficulties had become so serious that he flew to Vancouver on 9 October to negotiate the lease of his yacht Zaca. As Flynn and the 17-year-old actress Beverly Aadland, who had accompanied him drove to the airport on 14 October, Flynn began complaining of severe pain in his back and legs.
They went to the residence of doctor Grant Gould, who gave medication and a leg massage. Flynn rested before resuming his journey. After 20 minutes Aadland checked on Flynn and discovered him unresponsive. Despite immediate emergency treatment and a transfer to the general hospital, he did not regain consciousness and was pronounced dead. He was 50.
‘In like Flynn’ is a phrase meaning ‘having quickly or easily achieved a goal or gained access as desired’. In addition to its general use, the phrase is used to describe success in sexual seduction. It became associated with actor Errol Flynn, due to his reputation for womanizing, consumption of alcohol, and brawling.