A true overnight sensation, Errol Flynn ascended from Tasmanian obscurity to international stardom when he joined a then-unknown Olivia de Havilland to work for Michael Curtiz on the 1935 film Captain Blood. He stayed at the top for years, mostly by repeating himself so charmingly that it became tough to care that each Flynn character resembled the last. The times seemed to demand his kind of heroism. And when the times changed, he changed with them, at least for a while.
A Warner production made to capitalize on the then-rising demand for swashbuckling adventure films, Captain Blood—the first of five films in the Errol Flynn Signature Collection box set—casts the star as an Irish doctor who ends up on the losing end of 17th-century British politics, and becomes a slave in Jamaica. Circumstances turn Flynn from slave to pirate, in the process allowing him to find the keynote that would characterize his early career. His pirate-captain character flouts authority, but behind his mischievous eyes and devil-may-care attitude lurks a high-minded hero committed to a higher cause. He ends the film not by changing his wicked ways, but by bringing the world around to his way of thinking.
There's something tremendously satisfying about seeing a wronged rogue proved right, and Flynn refined that persona to perfection in the tremendously entertaining The Adventures Of Robin Hood (available elsewhere) before offering variations in the Technicolor Western Dodge City and the swashbuckler reprise The Sea Hawk, all helmed by Curtiz. These films find the studio system working at its peak, with arresting direction, Erich Korngold and Max Steiner scores, and the supporting cast (which usually included de Havilland and Alan Hale) all conspiring to squeeze as much entertainment as possible into the length of a feature. True, Curtiz and Flynn could hardly stand each other, but they made the collaboration work for 12 films. (Most of the time, anyway: The Private Lives Of Elizabeth And Essex throws Flynn into a lousy costume drama opposite a bizarrely made-up, literally shaky Bette Davis.)
With 1941's George Custer biopic They Died With Their Boots On, Flynn broke with Curtiz and took up with White Heat director Raoul Walsh. As history, it's mostly bunk. Flynn's Custer is a heroic, high-spirited, Indian-respecting dunderhead prone to plunging into battle without thought and winning the day in spite of overwhelming odds (until, of course, the odds catch up with him). Dramatically, however, it's much more interesting. There's a new world of doubt behind Flynn's mask of confidence, and ultimately, it's too much faith in the American way that leads to his undoing, in a theme that anticipates the noirs of the decade's end.
Offscreen, Flynn did himself in a little at a time, as the respectful but unblinking TCM documentary The Adventures Of Errol Flynn makes clear. But the self-destructive undercurrents weren't what made him a star. As the DVD collection progresses from the '30s to the '40s, the accompanying vintage shorts and newsreels become increasingly consumed with war, as America moves from the sidelines to the thick of the action. If it wasn't already clear that The Sea Hawk's Philip II was a Hitler stand-in, the contextual material casts it in the proper light. It's no wonder that a hero with a brash attitude and unwavering sense of right and wrong found such mass appeal. Flynn wasn't made to last, but he did his part anyway.