Captain Blood (1935) was the movie that made him an overnight star and also established the lovely de Havilland as an actress to watch. Flynn plays Peter Blood, a British doctor whose stint as an unfairly incarcerated political prisoner convinces him to become a pirate, dividing his time between plundering other ships and wooing the niece (de Havilland) of the cruel governor (Lionel Atwill) determined to bring him down. Working with limited screen time, fourth-billed Basil Rathbone nyuks it up as a duplicitous French pirate, and his sword fight with Flynn is just one of this classic's innumerable high points.
Dodge City (1939) spirited Flynn from the high seas to the Wild West, and the match proved so natural that the Australian actor found himself cast in several more sagebrush sagas over the ensuing years. But none could quite match this one, which if nothing else will always be remembered as the movie that served as the primary inspiration for Mel Brooks' Blazing Saddles. Flynn's cast as Wade Hatton, who, with trusty Rusty (Hale) by his side, sets out to clean up the title town by ridding it of all criminal elements. De Havilland's in this one, too, though even her beauty gets upstaged by a massive barroom brawl that even today retains its reputation as Hollywood's finest.
Like Dodge City, The Private Lives of Elizabeth and Essex (1939) was filmed in early Technicolor, and both movies suffer for it: While the images look fine in close-up, the colors tend to bleed in medium and long shots (not a problem in Robin Hood, which remains the most gorgeous of all Technicolor opuses). That's less a distraction in Dodge City than in this historical tale that relies on exquisite costumes and set designs for its atmosphere. But no amount of sloppy saturation can diminish the excellent performance by Bette Davis, whose Queen Elizabeth finds herself enamored with the dashing (and much younger) Earl of Essex (Flynn) even as her devious advisers (including Vincent Price as Sir Walter Raleigh) attempt to turn her against him.
Hale, Claude Rains and several other Warner reliables joined Flynn for The Sea Hawk (1940), an oceanic epic that's every bit as exciting as Captain Blood. Flynn is in fine form as Geoffrey Thorpe, a British commander and leader of the patriotic "Sea Hawks" who tries to convince Queen Elizabeth (Flora Robson) that Spain has grand ambitions to conquer the globe, including England. Leading lady Brenda Marshall pales in comparison to de Havilland (who's in every film in this set except this one), but Robson is magnificent as the Queen, rivaling Davis' spin in the role the previous year.
Warner's biopics weren't exactly known for their adherence to historical accuracy, yet They Died With Their Boots On (1941) is often so outlandish that viewers will instantly realize that history is getting assaulted and murdered right before their eyes. Yet the results are so entertaining that it's hard to get too indignant. Flynn delivers one of his best performances as General George Custer, whose career arc is traced from his days as a young cadet to his final stand at Little Big Horn. The Civil War battle scenes, as well as the Little Big Horn massacre (look for a young Anthony Quinn as Crazy Horse), are superbly staged, and the film also marks the final screen teaming of Flynn and de Havilland.
As with Warner's recent Gangsters Collection, each movie in the pack includes an incisive feature detailing the history of the film, as well as Leonard Maltin hosting "Warner Night at the Movies," which (emulating the moviegoing experience from decades past) includes a newsreel, a short film, a cartoon and a theatrical trailer before the main attraction. The set also includes a sixth disc containing the new 90-minute documentary The Adventures of Errol Flynn.
Captain Blood: ***1/2
Dodge City: ***1/2
The Private Lives of Elizabeth and Essex: ***
The Sea Hawk: ***1/2
They Died With Their Boots On: ***
- Matt Brunson