Please note there are plot spoilers to some films in this article. If you intend to binge-watch some Errol Flynn-Olivia de Havilland movies, I suggest not reading this article until afterwards.

“In late 1937,” wrote Errol Flynn in his 1959 autobiography My Wicked, Wicked Ways, “I completed the making of a super-costly The Adventures of Robin Hood. The first film, I think, in color. Another Jack Warner gamble…

…I developed a disgust for the mediocre vehicles to which I was assigned.”

– Errol Flynn, My Wicked, Wicked Ways, pub. 1959 p.208.

Thus Errol Flynn, right at the very end of his life, summed up the most successful years of his screen career, the years he spent at Warner Bros. between 1935 and around 1945.

What glorious years those must have been, those which are now referred to by historians as the Golden Age of Hollywood.

Yet Flynn detested those years. He looked back on them with anything but fondness and sentimentality. For one thing, he detested his most frequent collaborator: director Michael Curtiz. They made something like ten films together, including Captain Blood (1935), The Charge of the Light Brigade (1936), Four’s a Crowd (1938), Dodge City (1939), The Sea Hawk (1940)…oh, and that Technicolor costume picture, The Adventures of Robin Hood (1938).

At the bottom of this article, I will post a complete Flynn filmography, but there were other reasons why Flynn was not fond of those years. And most of those reasons had to do with women.

First of all there was the woman who was to become his first wife: French actress Lili Damita. In his book, Flynn claims that she bullied, blackmailed – nay, threatened him into marrying her. Flynn was an extremely intelligent individual; widely read, exposed to science, and interested in the arts and nature. Damita was interested in none of those things. The one thing that bound them together was that she was good in bed. But, Flynn admitted, even that couldn’t keep them together for long.

Flynn and Damita married on 29 June 1935 after she threatened to jump out of a window if they did not marry. This was her response to his admission of an affair. Hmmm – nice lady.

Flynn was many things, but one thing he was not was faithful.

He also describes his relationship with another woman whose behaviour towards him was distant, cold even, but yet he felt towards her something which he doesn’t describe outright, because I don’t think he knew what it was; his frequent co-star Olivia de Havilland.

He says in his book that he was “sure [he] was in love with her”, and I believe he was. He admits that he probably scuppered any chance of a meaningful relationship when he placed a dead snake in her underwear during the making of The Charge of the Light Brigade in 1936. This, it seems to me, was his one chance at real love, and he responded to it like a small child. That says a lot.

The real affection they held for each other, however, is played out on screen during all of the eight films they appeared in together. Indeed, the greatest scene the two of them played was the very last one, in which Flynn, as General Custer in They Died with Their Boots On (1941), parts from her, knowing that they probably won’t see each other again. As he turns to leave, Olivia de Havilland collapses to the floor in a heap, and in floods of tears. It’s as if they knew.

They never did see each other again, except once, briefly, around 1958, when de Havilland was so struck by his awful appearance that it remained with her for the rest of her long life (She died at 104 in 2020.) Many years of hard living, especially hard drinking, had taken their toll on Flynn. He had aged prematurely – indeed, he was to die in October 1959, aged 50, before his autobiography even had a chance at publication – and his face was covered in lines and liver spots. de Havilland could not understand how he had let himself go so completely.

There were two other women – Betty Hansen and Peggy Satterlee, both aged around 17 in 1942, when they accused Flynn of the crime of Statutory Rape. This is defined as sex with someone who is under the age at which they are legally able to give consent to the act. This case went to court, and Flynn was acquitted. It had been a conspiracy between the two girls, who claimed not to know each other.

There were other reasons why Flynn grew to hate his Hollywood years. There was the case of one of his films, Objective, Burma! (1945), in which British troops were not given sufficient credit for their role in the Burma Campaign. Flynn wrote that he believed he seemed to get the blame for the faults of that production, despite the fact that he had nothing to do with the script or the direction of that picture.

Flynn had a volatile relationship with his then-boss, studio head Jack L. Warner. Right at the start of his career, Flynn arrived on the set drunk, and of course word got back to Warner who called the actor to his office. Warner shouted and screamed at him for several moments, and then put his arm around him and asked him if he had any problems. All this while producer Hal B. Wallis sat watching meekly.

Errol Flynn hated Hollywood during its greatest years, and yet there must have been hundreds of thousands of men who would have given an arm just to be in Flynn’s shoes for ten minutes. Although probably not the same ten minutes during which he was being shouted at by Jack Warner.

Flynn Filmography

All films in black & white unless specifically mentioned.

1. In the Wake of the Bounty (1933) Dir Charles Chauvel 66 minutes. Made in Australia.
2. I Adore You (1933) Dir George King 74 minutes. Made at Warner Bros. in Great Britain.
3. Murder at Monte Carlo (1935) Dir Ralph Ince 70 minutes. Made at Warner Bros. in Great Britain.
4. The Case of the Curious Bride (1935) Dir Michael Curtiz 80 minutes. Flynn’s Hollywood debut.
5. Don’t Bet on Blondes (1935) Dir Robert Florey 59 minutes. Flynn’s first Hollywood speaking role.
6. All-American Drawback (1935) Dir Lloyd French 11 minutes. Edgar Bergen/Charlie McCarthy short.
7. Pirate Party on Catalina Isle (1935 Technicolor) Dir Gene Burdette 19 minutes. MGM short.
8. Captain Blood (1935) Dir Michael Curtiz 119 minutes. Flynn’s breakthrough role.
9. Screen Snapshots, Series 16 No.1 (1936) Dir Ralph Staub 10 minutes. Flynn & Damita seen together.
10. The Charge of the Light Brigade (1936) Dir Michael Curtiz 115 minutes.
11. Screen Snapshots, Series 16 No. 3 (1936) Dir Ralph Staub 10 minutes.
12. Breakdowns of 1937 (1937) Dir unknown 7 minutes. Unreleased publically; a compilation of outtakes.
13. Green Light (1937) Dir Frank Borzage 85 minutes.
14. The Prince and the Pauper (1937) Dir William Keighley 118 minutes. Despite top billing, it is 52 minutes before Flynn appears.
15. Another Dawn (1937) Dir William Dieterle 73 minutes. Flynn cast alongside Kay Francis.
16. The Perfect Specimen (1937) Dir Michael Curtiz 97 minutes. Flynn cast alongside Joan Blondell.
17. Breakdowns of 1938 (1938) Dir unknown 13 minutes. See film #12.
18. For Auld Lang Syne (1938) Dir unknown 7 minutes. Hosted by James Cagney.
19. The Adventures of Robin Hood (1938 Technicolor) Dir Michael Curtiz, William Keighley 102 minutes.
20. Four’s a Crowd (1938) Dir Michael Curtiz 93 minutes.
21. Screen Snapshots, Series 18 No.1 (1938) Dir Ralph Staub 10 minutes.
22. The Sisters (1938) Dir Anatole Litvak 99 minutes. First appearance alongside Bette Davis.
23. The Dawn Patrol (1938) Dir Edmund Goulding 103 minutes. All-male cast.
24. Dodge City (1939 Technicolor) Dir Michael Curtiz 104 minutes. Flynn’s first western.
25. The Private Lives of Elizabeth & Essex (1939 Technicolor) Dir Michael Curtiz 106 minutes.
26. Virginia City (1940) Dir Michael Curtiz 121 minutes.
27. The Sea Hawk (1940) Dir Michael Curtiz 127 minutes.
28. Santa Fe Trail (1940) Dir Michael Curtiz 110 minutes. Flynn’s fifth consecutive Curtiz picture.
29. Footsteps in the Dark (1941) Dir Lloyd Bacon 96 minutes. Second film alongside Brenda Marshall.
30. Dive Bomber (1941 Technicolor) Dir Michael Curtiz 132 minutes. Twelfth and final Curtiz film.
31. They Died with Their Boots On (1941) Dir Raoul Walsh 140 minutes. Last with Olivia de Havilland.
32. Breakdowns of 1942 (1942) Dir unknown 14 minutes. See Films #12 & #17.
33. Desperate Journey (1942) Dir Raoul Walsh 107 minutes.
34. Gentleman Jim (1942) Dir Raoul Walsh 104 minutes.
35. Edge of Darkness (1943) Dir Lewis Milestone 119 minutes.
36. Show-Business at War (1943) Dir Louis de Rochemont 17 minutes.
37. Thank Your Lucky Stars (1943) Dir David Butler 127 minutes. All-star musical in which Flynn sings.
38. Northern Pursuit (1943) Dir Raoul Walsh 93 minutes.
39. Uncertain Glory (1944) Dir Raoul Walsh 102 minutes.
40. Objective, Burma! (1945) Dir Raoul Walsh 142 minutes. Sixth Raoul Walsh film in under four years.
41. Breakdowns of 1944 (1945) Dir unknown 6 minutes. See Films #12, #17 & #32.
42. San Antonio (1945 Technicolor) Dir David Butler 109 minutes. Flynn’s third western.
43. Peeks at Hollywood (1946) Dir Irving Applebaum 9 minutes. Cameo appearance.
44. Never Say Goodbye (1946) Dir James V. Kern 97 minutes.
45. Cry Wolf (1947) Dir Peter Godfrey 83 minutes. Flynn stars alongside Barbara Stanwyck.
46. Escape Me Never (1947) Dir Peter Godfrey 104 minutes.
47. The Lady from Shanghai (1947) Dir Orson Welles 87 minutes. Flynn does not appear but acts as technical advisor for the yachting sequences.
48. Blow Ups of 1947 (1947) Dir unknown 18 minutes. More unintentional cock-ups.
49. Silver River (1948) Dir Raoul Walsh 110 minutes. Seventh Raoul Walsh picture.
50. Adventures of Don Juan (1948 Technicolor) Dir Vincent Sherman 110 minutes.
51. It’s a Great Feeling (1949 Technicolor) Dir David Butler 85 minutes. Cameo from Errol Flynn.
52. That Forsyte Woman (1949 Technicolor) Dir Compton Bennett. On loan to MGM.
53. Montana (1950 Technicolor) Dir Ray Enright 76 minutes.
54. Rocky Mountain (1950) Dir William Keighley 83 minutes.
55. Kim (1950 Technicolor) Dir Victor Saville 113 minutes. On loan to MGM (again).
56. Adventures of Captain Fabian (1951) Dir William Marshall 100 minutes. Flynn wrote the screenplay.
57. Hello God (1951) Dir William Marshall 64 minutes. Unreleased?
58. Mara Maru (1952) Dir Gordon Douglas 98 minutes.
59. Cruise of the Zaca (1952 Technicolor) Dir Errol Flynn 17 minutes. Documentary about Flynn’s boat.
60. Against All Flags (1952 Technicolor) Dir George Sherman 84 minutes.
61. Deep Sea Fishing (1952 Technicolor) Dir Errol Flynn 10 minutes. Guess what it’s about?
62. The Master of Ballantrae (1953 Technicolor) Dir William Keighley 90 minutes. Made in Great Britain.
63. The Story of William Tell (1953 Color) Dir Jack Cardiff ?? minutes. Short intended as a feature film.
64. Il maestro di Don Giovanni aka Crossed Swords (1954 Pathécolor) Dir Milton Krims, Vittorio Vassarotti 86 minutes.
65. Lilacs in the Spring (1954 Color) Dir Herbert Wilcox 94 minutes.
66. The Dark Avenger (1955 Eastmancolor) Dir Henry Levin 85 minutes.
67. King’s Rhapsody (1955 Eastmancolor) Dir Herbert Wilcox 93 minutes.
68. Istanbul (1957 Technicolor) Dir Joseph Pevney 84 minutes.
69. The Big Boodle (1957) Dir Richard Wilson 84 minutes.
70. The Sun Also Rises (1957 DeLuxe Color) Dir Henry King 130 minutes.
71. Too Much, Too Soon (1958) Dir Art Napoleon 121 minutes. Flynn plays his friend John Barrymore.
72. The Truth About Fidel Castro (1959) Dir Errol Flynn 59 minutes.
73. Cuban Rebel Girls (1959) Dir Barry Mahon 68 minutes. Flynn’s final, chaotic film.