The Golden Age of Hollywood was a pinnacle time for iconic duos such asKatharine HepburnandSpencer Tracy,John WayneandMaureen O’Hara, andWilliam PowellandMyrna Loy. While there are countless cinematic couples,Errol Flynnand two-time Oscar winnerOlivia de Havillandeffortlessly stole the hearts of audiences with their genuine real-life friendship and flirtatious on-screen chemistry. Ultimately, these two cemented themselves as one of the most alluring and complex on-screen duos in Hollywood history.
Flynn and de Havilland made their feature film debut in the classic swashbuckling filmCaptain Blood, becoming an instant hit with movie-goers and one of Warner Bros.’s top on-screen duos. Throughout their careers, Flynn and de Havilland collaborated on eight films together, including their most famous, 1938’sThe Adventures of Robin Hood. Eventually, the two formed a lifelong friendship, which further contributed to their timeless legacy on the big screen.This list will rank de Havilland and Flynn’s eight collaborationsbased on how memorable the movies are, how strong the actors' chemistry is, and the project’s overall quality.
8’Four’s a Crowd' (1938)
Directed by Michael Curtiz
De Havilland and Flynn co-star inFour’s a Crowd, which also starsRosalind Russell,Walter Connolly, andMargaret Hamilton. Russell stars as Jean Christy, a local reporter who tries to save her newspaper after her editor-in-chief, Robert Landsford (Flynn), clashes with the paper’s new owner, Pat Buckley (Patric Knowles). When Christy tries to make a deal with a public relations firm, she and Landsford learn that the owner’s granddaughter (de Havilland) is Buckley’s fiancé, leading Christy to pursue Buckley and Landsford to go after the granddaughter.
After the immense success ofThe Adventures of Robin Hood,Flynn had been concerned about being typecast as an action starand insisted on being cast in other genres, specifically the then-successful butnow-defunct screwball comedy. WhileFour’s a Crowdwasn’t a success at the box office,it still allowed de Havilland and Flynn to trade in their traditional dramatic pacefor a more lighthearted collaboration that showcases both stars' comedic chops and slapstick wit.
Four’s a Crowd
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7’The Private Lives of Elizabeth and Essex' (1939)
Based on the popular stage production,The Private Lives of Elizabeth and Essexis a historical romantic drama starringtwo-time Oscar winnerBette Davisas Queen Elizabeth I. It follows a fictionalized version of the relationship between the Queen and the Earl of Essex, Robert Devereux (Flynn). De Havilland takes on a supporting role of one of the Queen’s lady-in-waiting, Penelope Gray, who plays a crucial role in the romance between the aging Queen and the dashing Earl of Essex, entangling them in a torrid love triangle.
The Private Lives of Elizabeth and Essexwas a financial success, earning over half a million dollars, but much of the film’s praise went to Davis and her prestigious performance.Despite some reviews, Flynn effectively holds his own against Davis. Still,his few scenes with de Havilland are among some of the film’s most compelling and unforgettable, accurately alluding to them being a better romantic fit compared to Davis and Flynn.
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6’The Charge of the Light Brigade' (1936)
De Havilland and Flynn star in their second film together,The Charge of the Light Brigade, which is set during the Crimean War and leads up to the historical Battle of Balaklava. While action and violence play a vital role in the film, there’s also an underlying story of betrayal and redemption between Flynn’s character and his brother (Patric Knowles), who secretly steals the affection of his fiance (de Havilland).
According to Warner Bros.' financial ledger,The Charge of the Light Brigadewas amongthe studio’s most expensive productionsand has been noted as one of the year’s most popular films, mainly due to Flynn and de Havilland’s recent status as major box office draws.Flynn and de Havilland give spellbinding performancesinThe Charge of the Light Brigade, regenerating their authentic dynamic with romantic tension and compassion that initially captivated audiences.
The Charge of the Light Brigade
5’Santa Fe Trail' (1940)
Michael Curtiz’sSanta Fe Trailis based on the controversial anti-slavery campaign led by abolitionist John Brown, who, despite his honorable intentions, left immense bloodshed and destruction in pursuit of his crusade. Flynn stars alongside future presidentRonald Reaganas two recent West Point graduates who are stationed in Kansas, where they meet Brown (Raymond Massey). As the two cadets go head-to-head with Brown, the friends also find themselves competing for the heart of a charming Southern Belle (de Havilland).
Santa Fe Trailmarked the seventh film starring Flynn and de Havilland and was one of the highest-grossing films of the year for Warner Bros. While Reagan and Flynn are the main focus of the film,Flynn and de Havilland effectively convey their natural chemistry and passionin every one of their scenes, adding a unique quality and intriguingromance to this Western classic.
Santa Fe Trail
4’Dodge City' (1939)
Flynn and de Havilland take on their first Western together in the 1939 classicDodge City. It follows a lone cowboy turned successful settler, Wade Hutton (Flynn), who decides to clean up the lawless town of Dodge City, Kansas, and agrees to be the new sheriff. While Hutton tries to rid Dodge City of a gang of outlaws, a romance develops between him and Abbie Irving (de Havilland), who is one of several settlers in Hutton’s group.
While de Havilland gained success in various film genres, Flynn was concerned audiences wouldn’t accept him in the role of Hutton. However,Dodge Citywent on to become a major hit as well as one ofWarner Bros.’s highest-grossing filmsof 1939. Flynn and de Havilland bringa sentimental touch to this rough and rugged Western adventurewith their undeniable attraction and emotional connection.Dodge Cityis one of Flynn and de Havilland’s all-time best films together and a refreshing change of pace for the charming leading man.
Dodge City
3’They Died With Their Boots On' (1941)
Directed by Raoul Walsh
De Havilland and Flynn team up for another Western inThey Died With Their Boots On. It follows a fictionalized account of the life of General George Armstrong Custer (Flynn), with de Havilland starring as Custer’s wife, Elizabeth. The film starts with Custer’s early days at West Point and leads up to his final stand against Crazy Horse. Although Flynn and de Havilland are both at the top of their game in this Western, Flynn’s performance is credited as one of his finest.
They Died With Their Boots Onwas the final film starring Flynn and de Havilland (but they do appear together as themselves in the Warner Bros. filmThank Your Lucky Stars).Flynn and de Havilland are both gripping and movinginThey Died With Their Boots On, deliveringa fitting send-off to the now-beloved on-screen couplewho, at this point, had developeda real-life devotion and friendship. Their real-life connection ultimately heightened their final performance together as one-of-a-kind.
They Died with Their Boots On
2’Captain Blood' (1935)
Flynn and de Havilland made their feature film debut together inMichael Curtiz’sCaptain Blood, leading the on-screen duo to strike box office gold for Warner Bros. The movie tells the story of Dr. Peter Blood (Flynn), who, after treating a man who was wounded in a rebellion against King James, is convicted of treason and sold into slavery. Blood is purchased by a young, kindhearted woman, Arabella (de Havilland). Despite her good heart, Blood escapes to pursue a life of piracy, never expecting to cross paths with the beautiful Arabella again years later.
Captain Bloodis among the movies that ushered in the era of swashbuckling adventures and established Flynn and de Havilland as major up-and-coming stars and two ofWarner Bros.’s top classic contract players. De Havilland and Flynn give animpeccable performance together that is simply natural and unfeigned. WhileCaptain Bloodis widely noted for its significance to the film genre and thrilling action sequences, it alsoignited an unextinguishable spark between de Havilland and Flynn, defining it as their most crucial and pivotal film together.
Captain Blood
1’The Adventures of Robin Hood' (1938)
Directed by Michael Curtiz and William Keighley
Flynn stars in his signature role as the cunning Sir Robin of Locksley inThe Adventures of Robin Hood, with de Havilland as the lovely Maid Marian. The film follows the classic story of Locksley, who, along with his group of merry men, fights to protect the crown and the townspeople from the king’s tyrannical, cruel, and greedy brother, Prince John (Claude Rains).
Flynn and de Havilland inThe Adventures of Robin Hoodare consideredone of classic cinema’s greatest romances. The frequent co-stars give star-making performances that are intensely warm and the epitome of a fairytale romance that refrains from coming off as cliché and forced. AlthoughThe Adventures of Robin Hoodis packed full of epic performances and vibrance,Flynn and de Havilland’s flawless chemistry and depictions of heroism and romancedeem them to be one of the greatest on-screen couples in cinematic history.
The Adventures of Robin Hood
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