Film: The Private Lives of Elizabeth and Essex (1939)
Stars: Bette Davis, Errol Flynn, Olivia de Havilland, Donald Crisp, Alan Hale, Sr., Vincent Price, Harry Stephenson, Nanette Fabray
Director: Michael Curtiz
Oscar History: 5 nominations (Best Art Direction, Cinematography, Visual Effects, Sound, Scoring)
Snap Judgment Ranking: 2/5 stars
Each month, as part of our 2026 Saturdays with the Stars series, we are looking at the men & women who created the Boom!-Pow!-Bang! action films that would come to dominate the Blockbuster Era of cinema. This month, our focus is on Errol Flynn: click here to learn more about Mr. Flynn (and why I picked him), and click here for other Saturdays with the Stars articles.
Errol Flynn lasted as a movie star for decades, but as one who was pretty much unimpeachable in terms of his box office, this period lasted roughly from 1935-1942, at which point he was oftentimes the biggest star on the Warner Brothers lot, give or take Bette Davis & James Cagney. During this time, Flynn was married to the same woman, actress Lila Damita, but he had a history of womanizing. Like Gary Cooper before him, he had an affair with Lupe Velez, and would get drunk off of William Randolph Hearst's vodka. This reputation as a party boy was in stark juxtaposition to the men he'd play onscreen, frequently honorable scoundrels, or in the case of today's movie, a truly honorable man stuck in an impossible situation between two women. This would also pair Flynn with both of the actresses that he'd be most associated with in his career: Olivia de Havilland, whom he would have a largely amicable relationship with, and Bette Davis...with whom he would not.
(Spoilers Ahead) The film is a glossy historical melodrama, one where facts should not get in the way of a good monologue. Private Lives is about an aging Queen Elizabeth (Davis, in de facto kabuki makeup), who is clearly desperately in love with the handsome, popular Earl of Essex (Flynn), but cannot have him in the way that she wants because it would put at risk her power. She instead constantly finds herself at odds with him, usually in open court, and has fights with him, using her lover as a pawn in a number of battles, oftentimes risking his life as punishment for not returning her love in the way that she wants, because he's also power-hungry. This all happens while the beautiful Lady Penelope (de Havilland) is also pursuing the Earl, which in the film's final moments we're led to believe was nothing, and that Elizabeth was his own true love. Of course, at that point Elizabeth has publicly demanded the Earl's head for trying to be her equal, and there is no way out for the Queen, doomed to forever remain unmarried & unloved (except by England).
This is territory we've been to cinematically-Elizabeth's inability to find love because she is not beautiful and demands power instead has been informed by everyone from Helen Mirren to Glenda Jackson to Cate Blanchett to Margot Robbie (even Bette would go to this well twice). Davis, at the peak of her power and beauty, wears intense makeup that makes her look, well, hideous (and years older than she was), in some ways foreshadowing her later triumph in Baby Jane Hudson. But the movie, despite looking divine (the costumes, art direction, & cinematography are all a triumph, though why it got a special effects nomination at the Oscars is beyond me...the Scoring nomination is a bit cheeky given there's a song sung by Olivia de Havilland's character written by the actual Walter Raleigh, here played by Vincent Price in an early role), is kind of a snore. Davis overacts to the rafters (with diminishing returns), de Havilland is fun but too small of a part, and Flynn's performance is a bit underwhelming. Flynn is so grand in swashbuckling roles, but (as we'll see in the coming weeks), he was a somewhat limited actor when it came to going beyond that ken. He is breathtakingly beautiful in this-it takes an actress as confident as Davis to appear in this kind of makeup against Flynn, who looks like a Raphael painting in some scenes, and risk being thought ugly, but I don't think he can land some of the scenes, save for the last 15 minutes, when he's betrayed by Davis & they both seem to be in a much better movie.
Offscreen, Davis and Flynn were not close in the same way that he was with de Havilland, and it's hard to pinpoint the exact nature of their relationship given that Davis would outlive him by decades, and therefore be able to go on talk shows (and discuss in memoirs) what she thought of him, and regularly change her mind. She seemed to not like his ethics as an actor (finding he preferred celebrity more than the serious craft that Davis believed screen-acting), and also thought it beneath her to share billing with him in the film (you'll note, watching it now, that Davis, not Flynn, gets top billing, which makes sense in retrospect given her legend, but at the time would've been a genuine debate as both were equally valuable to Warner Brothers). Davis wanted Laurence Olivier, who wasn't famous enough to get a role like this in 1939 (Wuthering Heights had not come out when production was in motion), and at one point (according to Hollywood legend) actually slaps Flynn for real in one scene, rather than faking it as would be typical on a production, which caused Flynn to become ill. Davis, though, had kinder words about Flynn than I do in this movie, conceding that she thought him very good years after the fact while watching the movie, and telling de Havilland "he can act!"

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