It Takes Two: Errol Flynn and Olivia de Havilland

Cinematic partnerships are one of the great things about going to the movies. It is a joy to watch two stars with tremendous chemistry find different variations of making it spark. Occasionally, these pairings led to real-life romances (Bogie and Bacall remain the prime example) or were so omnipresent that the public thought their screen lives and private lives bled together (William Powell and Myrna Loy encountered this during The Thin Man years).

He was the Tasmanian daredevil of swashbucklers. She was the sweet but steely heroine of melodramas. He brought a lascivious and daring quality to even the most pedestrian of films, while she demonstrated a range and class that elevated even her flimsiest vehicles.

If Ginger Rogers gave Fred Astaire sex and he gave her class, then Flynn and de Havilland provided the same for each other. She brought a prim romance and sweeping elegance, although there was a spark in her eyes that clearly reveled in the mischief and mirth, and he brought a fantastical sense of play and masculine swagger to their chaste love stories and fairy book playgrounds. Sex and class, romance and adventure – these are the overpowering themes of their films together despite whatever costume trappings and settings are swirling around them.

They made eight films together, nine if you include Thank Your Lucky Stars, which given that it was a star-studded cameo-fest morale booster I am not. Although it is a notable film for featuring the only musical performances from the likes of Flynn, de Havilland, Ida Lupino, and, believe it or not, Bette Davis. So, I am focusing in on the eight film they made over a six-year period which launched their careers into the upper echelon of movie stardom and cemented their status as cinematic legends.

We begin with 1935’s Captain Blood, the film that not only launched Errol Flynn as a viable movie star but their screen partnership. Looking at it now, Captain Blood is an overstuffed dry run for the eventual tropes and formulas of their more successful pairings. This does not mean that their first film together is bad, it is not, it is merely shaggy.

Stranger still to think about how Flynn nearly missed on the chance. The studio originally wanted suave British leading man Robert Donat, but his chronic asthma caused him to pass on the role. Next up, the studio went into their staple of contract players considering the likes of James Cagney and Leslie Howard. Donat as aristocratic doctor turned pirate is feasible, but it is near impossible to picture Cagney’s live wire tough-guy act in the role. Same goes for Howard’s sleepy, slightly sour expression.

No, Errol Flynn was the picture man for the job. I remain unsure of just how good an actor he was, or what exactly was his range, but his wicked charms slip into the contours of this character and story so seamlessly that academic discussions about actorly technique become null and void in his presence. He had something up there on the screen as he wooed lovely women, did daring stunts, and flashed his roguish smile. The only piece missing here is his pencil thin mustache.

The same cannot entirely be said for de Havilland’s prudish good girl. She is filmed in downy lighting that emphasizes her dewiness and youth but is sacked with a rote character that does not give nearly enough opportunities for the steel and fire lurking beneath that strawberries-and-cream complexion and doe eyes to flicker out. She is, of course, going to fall for this witty, gallant rogue (who wouldn’t, honestly?), but the romance does not live-up to the giddy thrills of later films by keeping their characters so lopsided.

Perhaps it is simply a case of too much plot to power through within two hours? After all, we must witness Dr. Peter Blood get wrongfully accused, sold off into slavery in Port Royal, meet-cute with his love interest, escape on a stolen vessel, become a pirate, spar with his primary nemesis (Basil Rathbone, always the hissable villain), before returning to Port Royal to make good and woo his love interest. Oh, and he gets his reputation restored and becomes the new governor of Port Royal. Whew, that is a lot of movie for a compact two hours.

Props to director Michael Curtiz for keeping the pace moving along even as the script bogs itself down in one overly talky scene after another that feels less like imparting dramatic happenstance than exposition dumps in huge chunks at a time. Curtiz keeps your interest through one busy and overstuffed frame after another, which still somehow manage to envelope Flynn as a shiny beacon or tipping point for everything to orientate around. Given that the two leads were largely untested quantities with the studio, it is no surprise in hindsight that many of the dynamic sequences in Captain Blood feel anemic in comparison to the gems waiting for excavation in their upcoming pairings. Many of them also involving Curtiz and Rathbone.

Yet Captain Blood is still worth watching and not simply for its historical value. Yes, it pales next to their best films, but no one at the time knew what they were capturing. The best was yet to come, but this is a very good place to start. You cannot watch this and think anything less than “Now, THAT is a movie star.”

1936’s The Charge of the Light Brigade was proof that the studio was smart enough to realize they had something special on their hands, but not smart enough to know what to do with it. Instead of having Flynn and de Havilland engaging in charming light romance in a flamboyant fantastical adventure story, The Charge of the Light Brigade is a pro-colonial wartime story that finds the two at odds with each other. After all, here director Curtiz has Flynn valiantly trying to bring ‘civilization’ to parts of India before engaging in a suicidal military mission.

Suffice to say, this is an immediate letdown from the more enthralling Captain Blood. Flynn seems an ill-fit for the cuckold, and de Havilland’s palpable sexual chemistry with Flynn is ignored in favor of asking us to believe that her true love is Patric Knowles. Sure, he is handsome, but Flynn and de Havilland are clearly smoldering at each other while Knowles and de Havilland are incapable of even making one tiny spark.

 What is most interesting about this turgid, Hail Britannia exercise is how it highlights the burgeoning thrum of war. The United States’ official entry into World War II was still several years away, but the European contingent of Hollywood, always a sizeable portion of the town, was clearly prognosticating and whipping up morale even then. Granted, some of this was probably knowing that certain stars and films would play better overseas before the market(s) dried up. If Captain Blood was their first semi-storybook adventure/romance, then The Charge of the Light Brigade demonstrates that those artificial films are mere child’s play when the subject matter is the masculine drive of war and men under its pressures.

I disagree as the films that we remember them for are the grand adventures in period costumes and large sets. This entry is less a dual feature than a Flynn marquee with de Havilland in a thankless role as “the girl in the story.” No one comes to these films for grim reality or aggressively masculine posturing. We come to their films for the charm, wit, romance, and escapism they provide. The trio would get the formula exactly right in their next joint feature.

1938’s The Adventures of Robin Hood is their unequivocal masterpiece. Critic Don Druker stated, “movies like this are beyond criticism,” and he was correct given how The Adventures of Robin Hood is an immaculately produced technical marvel that is among the best that cinematic wonder has to offer. From this incarnation of the roguish hero comes seemingly every single other screen adaptation (both big and small, including Mel Brooks’ beloved parody) and bits and pieces can clearly be seen in the ways the fight choreography of Star Wars borrows liberally or the way it cemented Flynn’s screen persona for eternity. Before we think of Douglas Fairbanks in the role, we think of Flynn swaggering in with a deer slung over his shoulders filled with prideful bluster.

It unimaginable to picture this film in its original state: filled with arcane language, starring James Cagney and Anita Louise, and shot in black-and-white. So much of the magic and power in the film resides not just in the chemistry between Flynn and de Havilland, but in its more vibrant than real life Sherwood Forest and castles. In its glorious scenes of archery, knights in battle, and guerilla attacks that still emanate an awe and wonder than sparks our child-like sense of wonder at any age.

Much like the next year’s extravagant Gone with the Wind, The Adventures of Robin Hood was largely a creative enterprise taken on and overseen by a super-producer, Hal B. Wallis. It was his decision to jettison the arcane language for a plain-spoken manner that underscores the romantic fantasy of the story, the bright Technicolor, and cast Flynn and de Havilland after Cagney walked off the Warner Brothers lot during a dispute with the studio. Wallis was also responsible for director William Keighley being replaced with Michael Curtiz during production. While it is hard to know exactly who did what, the general consensus seems to be that Keighley was largely responsible for the outdoor sequences while Curtiz spruced up the action and the studio sets.

It all came beautifully together, chaotic production be damned, in a film that thrills because of its innocence. Robin Hood and Maid Marian are romantic figures, the noble rogue and beautiful damsel, without any need for recontextualization or gritty revisions. Robin Hood leaps, fires his arrows, steals from the rich, gives to the poor, romances his lady, and banters with the villains simply because he is Robin Hood and that is what the legend says he does.

All of this technical wizardry and splendor, reds and greens that are richer than anything in the real world in vast castle interiors that are accented with gold, led the film to Oscar glory. Of its four nominations (Picture, Art Direction, Editing, and Score), it only lost one (Picture to You Can’t Take It with You). The three awards it did win are among some of the best of its era. But all of this would be nothing without the actors occupying these grand halls and forest hideouts. Not just Flynn and de Havilland, but the assembly of contract players at the studio who outfit the colorful supporting parts with glee, humor, and menace.

Some of the highest marks go to Claude Rains’ Prince John, his effete reading of the character would clearly inspire Disney, and Basil Rathbone’s snarky, hissing villainy as Sir Guy of Gisbourne. Rains’ Prince John gluttonously eating at a banquet while Robin Hood dresses down his treason against his brother King Richard is the stuff of classic adventures and high-spirited cinema. Even better is a climatic, and punishing, fight between Sir Guy and Robin Hood that features Rathbone glowering and Flynn’s athleticism in their fullest bloom.

Flynn’s good cheer while doing all of these tasks is what made his legend. I always think of a scene of him swaggering into a banquet with a deer draped across his shoulders when I think of him and this film. It is a powerful bit of movie star mythmaking. “Handsome devil” is what comes to mind when thinking of Flynn, and scenes like that are why. Even when facing incalculable odds stacked against him, Flynn exhibits a joy of performance that radiates off the screen. Sure, he had limitations as an actor, but within this context he was peerless and one of the greats.

What thrilled and enchanted me as a child watching this is still what enraptures me as an adult. The daredevilry involved in the sword fights, Flynn clearly performing the majority of the stunts himself, the studio contract players adding unique texture and color, and de Havilland’s great beauty, and the chivalric love story slowly playing out as a through line. Some movies and their charms are eternal. This is one of them.      

Another 1938 release, Four’s a Crowd, is a demonstration of how inherent casting is to successfully pulling off a comedy. While Errol Flynn is maybe not quite at home in comedies, his natural charisma and good looks carry a lot of the load. In contrast, Rosalind Russell doing a dry-run for Hildy Johnson here offers her trademark rapid-fire verbal quips and tough working girl cool. While Olivia de Havilland gives such a wonderfully daffy comedic performance that it underscores why James Cagney sang her praises and her range as an actress in his later years. Patric Knowles is… there. His handsome blandness worked as one of the Merry Men in Sherwood but reveals just how limp he was as leading man material.

The script is fine, serviceable enough but lacking in wit, and perhaps could have been salvaged by the likes of Leo McCarey. Journeyman Michael Curtiz is not exactly the first choice that springs to mind when thinking of directing a convoluted screwball comedy, and his work moves along at a brisk clip but lacks oomph. He would feel much more attuned and at home in the more masculine adventure stories he helmed for the duo.

The story plays out like Libeled Lady but without the foursquare star wattage to overpower the limitations. Newspaper owner (Knowles) is encountering problems with his editor-in-chief (Flynn) and a reporter (Russell) wants to save it. Knowles’ girlfriend, an heiress (de Havilland), and her filthy rich grandfather (Walter Connelly) get roped into the whole scheme. The four stars romance and change partners and allegiances until the final reel when Knowles and de Havilland and Flynn and Russell wind up the romantic pairings.

That last bit gets a great farewell joke. As Flynn and de Havilland kiss passionately in the back of a (incredibly spacious) cab, their spouses interject. They part and de Havilland says “my error” in a manner that sounds like “bye, Errol.” We are so used to seeing them getting pared off as the credits roll that them not winding up as the end goal leaves you a bit stumped. While not the weakest pairing between them, Four’s a Crowd is definitely in the lower-tier especially coming right after the euphoric highs of Robin Hood.  

1939’s Dodge City is the finest of the westerns that they made together, and the best of Flynn’s limited forays into the genre. While not quite a top-shelf genre entry, it is a thoroughly enjoyable spin through the struggle to clean up a violent cattle town. I wonder what would have happened if everything remained in place but we swapped out Michael Curtiz for John Ford, Howard Hawks, or Anthony Mann, artists renowned and known for elevating the western.

No matter, Dodge City is smart enough to keep a propulsive energy that barrels forward, like its climatic train on fire. We get a stampede, one of the finest (and largest) barroom brawls, and that aforementioned fiery train sequence all in 104 minutes. Toss in some scenes of Ann Sheridan as a tough-talking saloon girl and a romance between Flynn and ingenue-mode de Havilland and it offers you a lot in its slim package.

But Errol Flynn is too much of a dapper persona for the Old West. He sticks out with his odd, semi-British accent and refined body carriage in a story set in the post-Civil War era. While he still manages to project his joyous spirit and elegance, he never quite settles into the cowboy role. Apparently, he was uncomfortable with the prospect for all the reasons I have outlined and that mild discomfort with the material is occasionally viewable on his face. He makes so much more sense as a gentlemanly pirate or a roguish figure from folklore than he does as Civil War veteran.

Meanwhile, de Havilland was growing despondent with these thinly written and unchallenging parts. According to de Havilland, this string of uncomplicated, lady-like parts left her bored and unable to memorize her lines. A certain bit of frustrated energy is captured behind her eyes as her character disappears for long periods of time before showing up again consistently in the final third. Her part is easily reduced to “love interest” and it is no shock that she coveted parts like Melanie Wilkes and sued the studio over its arcane contractual obligations.

I bring up the discomfort and boredom of the leads to demonstrate why Dodge City is so frustratingly near greatness while occasionally touching it. Working to offset their ennui, Bruce Cabot, Victor Jory, Alan Hale, and Sheridan are clearly having a hoot and holler playing up these stock characters. And Curtiz manages to generate sustained dramatic tension from its love story (Flynn and de Havilland first meet when he kills her no-good brother before a stampede), its wild town in need of taming (they kill a kid in a pretty gruesome way), and its mustache twirling villains (Cabot is a self-glazing ham). It is a glorified B-movie made with all the prestige trappings and budget that goes along with an A-list feature.

Also released in 1939, The Private Lives of Elizabeth and Essex is a tour de force for Bette Davis, playing twice her age and masticating the scenery, which demonstrates the acting limitations of Flynn and has de Havilland in a thankless supporting role. I guess no one warned Flynn to fasten his seatbelts as his nervousness about taking the role caused him to frequently flub lines and arrive late. Allegedly, Curtiz threatened to replace him with Vincent Price, who appears in a minor role as Sir Walter Raleigh. Yet Davis got along swimmingly with de Havilland and the two remained lifelong friends. They often spoke highly of each other as people and of their work, including how they both sued the studio for less restrictive contracts and better parts.

Davis was widely tipped to get an Oscar nomination that year, and the smart money was on Private Lives to be the vehicle. Instead, it came from Dark Victory, a melodrama with Davis against type as a good girl with a terminal movie illness. Posterity has proven that the Academy got it right. Not that Davis isn’t a treat, especially when twisting her performance into a camp spectacle, but this kind of neurotic scenery-chewing was already part of Davis’ charm and persona.

And The Private Lives of Elizabeth and Essex is a bit of pomp and circumstance that feels like the aged prestige film it is. Flynn is outmatched as an actor but, my god, what a movie star he was! Davis and Flynn hated each other, a scene where she slaps him is the real deal, and she thought he was inadequate to the challenge of holding his own against her onscreen and wanted Laurence Olivier, then an unknown actor to American audiences. The mind spins conjuring up Davis and Olivier locked in ferocious verbal battles.

Years later, Davis would watch the film with de Havilland and remark that she was wrong. Flynn was good in the part in her reassessment. I would not go that far as she gets more enjoyment and mileage out of sparring with someone like Claude Rains than the buoyant and boyish Flynn. But Davis and de Havilland would go on to costar several times and make for a nice contrast against each other. Davis in her Brechtian manner and de Havilland concealing thoughts behind those doe eyes that are darker and more disturbed than she initially seemed capable.

If I have spent a lot of time talking up Bette Davis instead of the ostensible focal points of this essay it is simply because no matter what the title of the movie actually is, this is The Bette Davis Show to the core. Flynn keeps his chin up and merrily goes to the hell she sends him. But de Havilland’s thinly-written supporting part was retribution from Jack Warner for participating in Gone with the Wind and getting all the glory for a rival’s production. They are secondary figures to Warner Brothers’ then reigning queen of the lot.

An entertaining if not totally successful film that tries to combine a frontier adventure story with a moralizing message, 1940’s Santa Fe Trail ends up being a bit of a mess, but it has its moments. Flynn and de Havilland had the kind of chemistry that can make any piece of work watchable no matter its qualities, which is good since Trail needs a lot of help. While Santa Fe Trail is horrific as history, but when has that ever been the strongest point in Hollywood storytelling, it is also problematic and tonally inconsistent about its desire to be either a romantic adventure story or a sermon disguised as a western. It has less to do with the titular trail than it does as a back-handed compliment for Abolitionists.

For every great shoot ‘em up scene there is another which positions Abolitionists as zealots with quite a few loose screws, even if their end goal is justified. This split personality is not helped by any of the supporting actors – Raymond Massey and Van Heflin would turn in far better performances in other films and here decided to chew the scenery and act like ridiculous fire-and-brimstone caricatures. The film’s presentation of the black characters is both symptomatic of the times and a clear hedged bet that they did not want to offend the southern audience. The presentation of blacks as child-like and naïve is something any viewer of old films will just have to get through, but once we are told that they are by and large completely ignorant of their circumstances I had reached my limit.

But I will give the film credit for presenting the main characters as divided and shades of gray over the major conflict of the plot. They are more like defined pros and cons engaging in debates that push the others to explore the murky middle ground, and it gets heavy-handed if well-intentioned at times. Yet this is also hampered by a series of noncommittal lines again rendering Santa Fe Trail as a cursory and curious experience.

As for what the title has to do with the story – nothing other than a quick and cursory mention and stop. None of the main action has anything to do with the real Santa Fe Trail, so who knows why the film was dubbed this. To call it uneven would be putting it mildly, but Santa Fe Trail has its moments. I do not know if the rest of the film is worth the trip to get to them, but if you are a fan of Flynn, de Havilland or Curtiz, I suppose you must give it a glance. (Santa Fe Trail is in the public domain which makes it the most easily accessible film in the Flynn/de Havilland series.)

Their final film, 1941’s They Died with Their Boots On, revisits similar narrative and historical terrain as Santa Fe Trail. Whereas that film was critical of abolitionist John Brown and his anti-slavery campaign in the leadup to the Civil War (remind me again how Hollywood is a liberal paradise?), They Died with Their Boots On is a fictionalized portrait of George Armstrong Custer. Hollywood has always had a specious understanding and relationship to historical truth, which is occasionally fine for the purposes of dramatic need and narrative movement, but this is just revisionism masquerading as a historical epic.

They Died with Their Boots On slowly, ever so slowly, emerges as nothing but a star vehicle for Flynn that gives him a chance to play a frontier hero to stand alongside his swashbuckling rogues and daredevil aviators. But his star charisma and presence are better served by those rogues and legendary figures. They can handle his outsized sexual magnetism and bad boy charms better than Custer, a blowhard who was great at publicity and had a wife who stoked his largely fictitious claims after his premature death.

The whole thing is a bit too somber for the likes of Flynn. He needed more braggadocio and happy-go-lucky adventures to feel fully formed and coherent in a film. He was not exactly a great thespian, and that is where de Havilland often picked up the slack to counterbalance their pairings. The context around him mattered. He made sense as a fallen man turned romantic pirate or as a bareknuckle boxer (Gentleman Jim is perhaps his finest acting hour). The Custer presented here has nothing to do with the real person, even by Hollywood’s already flimsy standards, and everything to do with pouring Flynn’s megawatt smile and trademark mustache into another outsized personality.

At least Flynn and de Havilland are clearly having fun in their romantic scenes together. While not quite believable as a tongue-tied military man in the face of this feisty love interest, they are in simpatico in a love scene where he keeps trying to avoid her father’s protective gaze. He brought out the sense of mischievous fun that de Havilland possessed off-screen, just look at her bloopers filled with beautifully enunciated swear words, like no other co-star (except for maybe James Cagney in The Strawberry Blonde). And while it is nice to see de Havilland and Hattie McDaniel acting opposite each other (seriously, their staircase scene in Gone with the Wind is some of the best work in both of their careers), McDaniel is once more squandered in a role that lacks imagination and reveals the horrid racial attitudes of the time.

Same goes for all of the scenes involving the indigenous characters, especially a young Anthony Quinn as Sitting Bull who gets referred to as “boy” by Flynn’s Custer. Quinn is wasted in the role, which a bit amazing considering he was largely an actor who exploded on the screen no matter the size of the role. A small part in The Ox-Bow Incident shimmers with his coiled tension threatening to explode at any given moment, for example. But this gargantuan film swallows up a lot of the good of the various players involved with its sheer length and uneven sense of adventure and action.

Strange to think that this, the lone film not helmed by Curitz, was handled by Raoul Walsh, a pioneering director of such classics as Thief of Bagdad, White Heat, and The Roaring Twenties. He manages a mixed bag here, but his action sequences cannot be faltered. It is just everything orbiting around them that feels so largely formless, reductive, or grossly revised. Yet he still manages one of the finest scenes in all of the Flynn/de Havilland films in the final goodbye between Custer and Libby. A scene that is doubly poignant for the fact that this was also the farewell for the screen pair.

Flynn would die young at age 50, his real life was as large, expansive, and adventurous as one of his movies. There would also be the posthumous controversies, specifically that of his relationship with Beverly Aadland, and the inevitable reappraisal of his career. Charles Higham’s biography did damage for a time before largely being sued, corrected, and counterargued out of the popular consciousness. (If Higham were to be believed, then Timothy Dalton’s character in The Rocketeer was a fictional surrogate for Flynn’s real-life activities.)

While de Havilland would spend the remainder of her life being asked about their chemistry, talking openly about how much she adored working with him, how the rapport we saw on the screen carried over into real life with the two being flirtatious but chaste with each other. She would go on to win two Oscars, become one of the finest actresses of her generation, and demonstrate an envious range as a performer. But what endures are her sterling performances in works as varied as her Flynn vehicles, A Midsummer Night’s Dream, The Snake Pit, and The Heiress.

They were an unlikely duo, the cad and the lady, but they were one of the greatest pairings in the history of cinema. Her sweet, virginial face in their earliest films alight with awakened sensuality and playfulness at the sight of Flynn in full swagger. Spending time with them, even in their weakest vehicles, is never entirely without merit. My only hope is that something like The Adventures of Robin Hood continues to impress young minds like it did mine watching it on VHS in my grandparent’s living room. They are a gateway to worlds of pure imagination, romance, and daring.