Too Much, Too Soon (1958)

Too Much, Too Soon (1958)

[6] Dorothy Malone and Errol Flynn play father and daughter John and Diana Barrymore, real-life members of Hollywood's famous Barrymore family, both of whom suffered famously from alcoholism. Flynn is very good here in the final noteworthy role of his…
Montana (1950)

Montana (1950)

[4] Errol Flynn clings to the last few years of his good looks in Montana, before his opium and alcohol addictions sent him to an early grave at the age of 50. Montana seems unintentionally silly to me -- it's…
Captain Blood (1935)

Captain Blood (1935)

[8] Warner Brothers caught lightning in a bottle when they took a chance on a relatively unknown Tazmanian actor and cast Errol Flynn as Peter Blood in the Oscar-nominated crowd pleaser Captain Blood. Flynn became an instant star with his…
The Dawn Patrol (1938)

The Dawn Patrol (1938)

[8]

Errol Flynn and David Niven star as World War I pilots confronting the grimmest odds of survival in this exciting and moving remake of Howard Hawks’ 1930 original. With its wartime setting and nary a woman in the cast, The Dawn Patrol is another great bromance in the grand tradition of war stories — it’s all about camraderie, brotherhood and sacrifice.

The Private Lives of Elizabeth and Essex (1939)

The Private Lives of Elizabeth and Essex (1939)

[7] Bette Davis plays Queen Elizabeth the first, in love with Errol Flynn's Earl of Essex, in this period technicolor drama from director Michael Curtiz (Casablanca, The Adventures of Robin Hood). Both stars conjure the necessary pathos of their characters'…
Gentleman Jim (1942)

Gentleman Jim (1942)

[7]

Errol Flynn plays a banker who takes up boxing and makes it all the way to a climactic match against the heavyweight champion of the world. Gentleman Jim is more entertaining than I imagined, thanks to Flynn’s persistent charm and healthy doses of wit and humor. Alan Hale returns to Flynn’s side, this time playing his proud papa, while Alexis Smith takes over the leading lady duties. She’s no De Havilland, but she holds her own in a romantic subplot that is unusually tolerable for the time.

The Aviator (2004)

The Aviator (2004)

[9] Martin Scorsese directs Leonardo DiCaprio in this biopic of Howard Hughes, the billionaire aviator, filmmaker, and playboy whose considerable ambition was tragically counterbalanced by his mental illness. The Aviator opens with Hughes' mammoth, three-year-long production of the aerial battle…
Edge of Darkness (1943)

Edge of Darkness (1943)

[10] If you want to watch Errol Flynn fight the Nazis, this is your movie! Edge of Darkness is one of those great old World War II propaganda films, this time told from the perspective of a small Norwegian fishing…