No man has personified a film genre like Errol Flynn. He is the icon of Swashbuckling. He was rarely acclaimed for his acting, which is unfortunate. He may have been limited both in his abilities and in his opportunities, but given the right part, no one was better. Who else could wear tights and project pure masculinity? He could stand on a tree branch, laughing, wearing a funny little hat with a feather, his hair curled, and look completely natural, comfortable, and manly. That’s some kind of weird skill.
Flynn costarred with Olivia de Havilland in eight films. While pairings of other major stars tended to be structured to consistently give the couple a happy ending (in similar type films), that wasn’t the case with these two. Only half of the time did they end up together, and in three, Flynn died.
Flynn is an exception to the rule that while women are not allowed to age gracefully in Hollywood, men are. As soon as a few lines creased his face and he added a few pounds, his career was over.
While remembered as an action star, Flynn also was very effective in comedies—that shouldn’t have been surprising as he could be funny in those action parts. His eight films are made up of four Swashbucklers, three comedies, and one WWI film.
An honorable mention to Don’t Bet on Blondes (1935), where the yet-to-be-a-star Flynn has a long cameo. The star was Warren Williams as a bookie turned insurance agent and Flynn was a suitor for a girl whose father had bought anti-marriage insurance. Clearly, this was a comedy.
#8 – Adventures of Don Juan (1948) — The last and least of Flynn’s epic Warner Bros. Swashbucklers, it is a fun farewell to an aging sub-genre and an aging star. (Full Critique)
#7 – The Charge of the Light Brigade (1936) — This is the least of the major British-in-colonial-India adventure films, mainly due to the weak romance (poor Olivia de Havilland gets stuck with the worst role of her career). It is also bizarrely historically inaccurate (they didn’t even get the guns right, much less the reason for the charge) and the production was so vile it caused animal welfare laws to be passed. But Errol Flynn is charming, the combat exciting, and it all looks spectacular. [Also on the Olivia de Havilland list]
#6 – Four’s a Crowd (1938) — Flynn is a charming cad who runs positive PR for the worst people. It’s a romantic comedy and one of his pairing with Olivia de Havilland. [Also on the Olivia de Havilland list]
#5 – Footsteps in the Dark (1941) — Flynn plays a respectable man who secretly writes lurid murder mysteries and stumbles upon a real murder.
#4 – The Dawn Patrol (1938) — One of the finest war pictures, with Flynn, Basil, Rathbone, and David Niven as WWI pilots in horrible situations, having heroism forced upon them. [Also on the Basil Rathbone list]
#3 – Captain Blood (1935) — The first of the three great Flynn Swashbucklers. Flynn is a physician forced into piracy. His costar is Olivia de Havilland. (Full Critique) [Also on the Olivia de Havilland list and the Basil Rathbone list]
#2 – The Sea Hawk (1940) — The last of his three great Swashbucklers, it shares much of the cast and crew with Captain Blood and The Adventures of Robin Hood. Besides being a fine adventure film, is was a solid piece of propaganda for an England that needed it. (Full Critique) [Also on the Olivia de Havilland list]
#1 – The Adventures of Robin Hood (1938) — The greatest classic Swashbuckler and one of the Best films ever made. It is beautifully shot, with a wonderful score and a strong supporting cast, including de Havilland. It is here that Flynn became an icon. (Full Critique) [Also on the Olivia de Havilland list and the Basil Rathbone list]