By Jessica Pickens
With a winning smile and dashing good looks, Errol Flynn’s film characters always save the day. Though he’s most famous for his role of Robin Hood of Sherwood, Flynn played a variety of debonair heroes in multiple types of settings.
Flynn played many swashbuckling leading men in costume dramas. However, he also often found himself in World War II dramas and even Westerns!
No matter if he was wearing tights, a cowboy hat or Army fatigues, Errol Flynn’s charm shines through in these films:
Prince Edward Tudor’s (Bobby Mauch) life is in danger. It’s discovered that a poor boy named Tom Canty (Billy Mauch) looks identical to the prince. Miles Hendon (Errol Flynn) protects the prince, who is posing as Tom the pauper, from the Earl of Hendon (Claude Rains), who is the only person who can tell the prince and the pauper apart.
Real life twins Bobby and Billy Mauch star as the prince and the pauper in one of their many films together. This film adaptation of Mark Twain’s novel is one of several, with versions dating back to 1909.
King Richard the Lion Heart (Ian Hunter) overthrown by his brother King John (Claude Rains). Robin Hood (Errol Flynn) steals from the rich and gives to the poor as he leads his group of Merry Men to get King Richard back on his rightful thrown. In the process, Robin Hood falls in love with Maid Marian (Olivia De Havilland).
“Robin Hood” is probably Errol Flynn’s best-known film and is filmed in Technicolor. It’s the third out of eight times that Flynn and De Havilland co-starred.
Wade Hatton (Errol Flynn) is a cattle agent and travels to Dodge City, KS. When he sees the constant shooting in the streets and the innocent lives affected, he takes the job of sheriff to clean up the town.
Australian Errol Flynn was uncomfortable taking a role in a western since his Wyatt Earp-like character was supposed to be American. The script adds a few lines where Alan Hale explains Hatton’s world travels, to help speak to his accent.
In a fictionalized biographical film about George Armstrong Custer (Errol Flynn), the film follows Custer in the 1800s as he enters West Point and is branded as a troublemaker. He falls in love with Libbie Bacon (Olivia De Havilland) and the two eventually marry. Custer is placed with the 2nd United States Calvary and the film follows him as he serves in the Civil War. The film ends with Custer’s Battle of Little Bighorn with the Native Americans.
“They Died with Their Boots On” was one of the highest grossing films in 1941 and was the last feature film collaboration for Errol Flynn and Olivia de Havilland.
In the 1890s, boxing is illegal and leaders in San Francisco are trying to clean up the sport’s image with boxers who come from respectable jobs or positions. Jim Corbett (Flynn), a bank teller is recruited as a fighter and he rises in the sport as a professional prizefighter while introducing a more sophisticated style of boxing. Corbett becomes the new Heavyweight Champion, defeating the reigning champ, John L. Sullivan (Ward Bond).
Gentleman Jim (1942) is a loose biographical film on the real boxer James Corbett, a.k.a Gentleman Jim, who died in 1933. Corbett’s love interest in the film, played by Alexis Smith, is a fictional character. The film was based on Corbett’s autobiography, “The Roar of the Crowd.”
During World War II, Capt. Nelson (Flynn) leads a group of United States Army paratroopers through Burma in a mission against the Japanese Army. The film is narrated by a war correspondent (Henry Hull).
The war correspondent in the film was based on real-life war journalist Ernie Pyle, who was killed by a sniper in 1945 in Okinawa, Japan. In real life, Errol Flynn tried to enlist in World War II, but was deemed unfit for service due to several health conditions.
Jessica Pickens is a North Carolina-based writer. She has a degree in print journalism and now works in public relations. Outside of work, she writes about pre-1968 films at CometOverHollywood.com with a special interest in musicals, films released in 1939, and World War II-era films. You can follow her on Twitter, Instagram, and Facebook.