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Monday Nights in April | 41 Movies 

A rogue. A swashbuckler. A gentleman…of sorts. The wicked, wicked ways of April’s TCM Star of the Month Errol Flynn are as fabled as the epic tales to which he lent his charismatic wit and style. Whether romancing Olivia de Havilland in a historical adventure on screen or side-stepping contract suspensions courtesy Warner Bros. studio boss Jack Warner, Flynn holds a rare status that rises above movie actor and truly qualifies for the overused term “icon.”

Yet Flynn’s fall from Hollywood grace was perhaps the saddest of those Golden Age icons. His seminal autobiography My Wicked, Wicked Ways (co-authored by ghostwriter Earl Conrad) was released by G. P. Putnam’s Sons just two months after Flynn’s sudden death at age 50 in 1959. The rights to his story were purchased for the seemingly paltry sum of $9,000, a deal taken by a performer that Hollywood either didn’t want or just simply couldn’t risk gambling a project on anymore. His last film, Cuban Rebel Girls (1959), a barely-watchable, semi-biographical story in and of itself, was produced on the cheap in Cuba. His last studio projects, Too Much, Too Soon (1958) and The Roots of Heaven (1958), had major talent behind them, including Oscar-winners like Dorothy Malone and John Huston, but were considered disappointments.

By the time the 1950s rolled around, Flynn’s penchant for booze and hard living had taken its toll on his health, finances, appearance and reputation. He never stopped working, but the heights of his early fame were never again approached. Still somehow, the sheer legend of Errol Flynn ultimately grew greater after his death. The posthumous timing of his memoir propelled the book to blockbuster status, and it has never been out of print. The stories spun throughout are jaw-droppingly blunt, humorous, self-reflective and, oftentimes, unbelievable. As his final act, Flynn managed to produce a work that launched his screen persona into myth.

And what a myth it was.

In describing his birth in My Wicked, Wicked Ways, Flynn led by writing, “Better begin where it all begins—in the womb—except where, as in my unique case, it so often ends.”

Errol Leslie Thomson Flynn was born in Tasmania on June 20, 1909 to Australian parents, a marine biologist and college educator father and a distant mother, who branded him “a nasty little boy.” Flynn had a childhood and young adulthood that saw him in a series of outrageous sexual liaisons, kicked out of school, caught in an embezzling scheme and mining for gold in New Guinea. And that was just by the age of 17. He claimed to have worked every odd and unusual job imaginable, including as a gigolo, a pearl-diver, a diamond smuggler, a charter-boat captain and a bird-catcher.

Eventually, Flynn’s myth segued into motion pictures after his looks caught the eye of an Australian producer. He appeared in his home country as Fletcher Christian in the first sound adaptation of Mutiny on the Bounty, In the Wake of the Bounty (1933). Warner Bros. took note of the actor’s spark and shipped him across the Pacific to Hollywood, where he started his long tenure as a WB contract player. After appearing in bit parts in Murder at Monte Carlo (1935), The Case of the Curious Bride (1935) and Don’t Bet on Blondes (1935), Flynn was launched into superstardom when he was cast as the lead in Captain Blood (1935), alongside then-equally-unknown Olivia de Havilland. The pair were quickly reteamed in The Charge of the Light Brigade (1936), setting a historical, swashbuckling pattern for Flynn’s future films.

He appeared occasionally throughout the 1930s in non-action movies, including Green Light (1937), co-starring Anita Louise, Another Dawn (1937), co-starring Kay Francis and The Perfect Specimen (1937), his first comedy co-starring Joan Blondell.

But Warner Bros. kept Flynn’s steady stream of action flicks consistently on theater marquees, and his box office prowess allowed the often-frugal studio to spring for Technicolor in such epics as Dodge City (1939), Dive Bomber (1941) and San Antonio (1945). They even gave a newly-erected sound stage, capable of holding large ships in a gigantic water tank, the moniker “The Sea Hawk Stage” in honor of its inaugural production, The Sea Hawk (1940).

Flynn worked often with WB favorites, including director Michael Curtiz, with whom he collaborated on 12 pictures, among them Four’s a Crowd (1938), Virginia City (1940) and Santa Fe Trail (1940). He also teamed with director Raoul Walsh seven credited times in movies like Gentleman Jim (1942) and Silver River (1948). He worked with the studio’s undisputed queen Bette Davis twice, in The Sisters (1938) and The Private Lives of Elizabeth and Essex (1939), though they infamously did not get along. Flynn seemed to enjoy goading Davis, slipping his tongue into her mouth during kissing scenes. Davis repaid Flynn by making what was supposed to be a fake slap real during a sequence for The Private Lives of Elizabeth and Essex. Olivia de Havilland said that years later she watched part of the film on television with Davis, and afterwards Davis begrudgingly exclaimed, “Damn it! The man could act!”

De Havilland proved to be his most popular co-star with audiences, and the eight films they made together remain amongst their most-widely seen. The Adventures of Robin Hood (1938) was arguably their most successful outing, casting them as Robin Hood and Maid Marian, respectively. One of the top money-makers of the year, the movie took home three Academy Awards for its art direction, film editing and its classic Erich Wolfgang Korngold score. It was also nominated for best picture. In 2003, the American Film Institute named Flynn’s Robin Hood the 18th greatest hero in cinematic history.

The star’s last pairing with de Havilland was They Died with Their Boots On (1941), which found him playing another historical figure in battle, this time General George Custer. Their last scene plays poetically with the hindsight they’ll never act together again. His final words to de Havilland’s Elizabeth Custer are, “Walking through life with you, ma’am, has been a very gracious thing.” While their chemistry lit up movie houses and each claimed to have had crushes on the other, both parties maintained they never acted on their attraction. De Havilland told People in 2016, “there are no word to describe my feelings for Errol Flynn.”

Due to various health concerns, Flynn was unable to enlist in World War II, but he appeared in a number of war-themed roles during the 1940s, including Desperate Journey (1942), Edge of Darkness (1943), Northern Pursuit (1943) and Objective, Burma! (1945). During the decade, Flynn also first dabbled in producing with a crime drama co-starring Paul Lukas, Uncertain Glory (1944). His Technicolor epics continued with Adventures of Don Juan (1948) and Montana (1950). He made his only foray into film noir with the potboiler Cry Wolf (1947), co-starring one of the genre’s stalwarts, Barbara Stanwyck.

Due to Flynn’s caviler attitude and frequent drunken antics, he was often at odds with studio head Jack Warner. Warner Bros. tour guides still regale guests with tales of how Flynn managed to hide booze, banned from Errol Flynn pictures, around his movie sets and dressing room. He was even said to inject oranges with vodka so to sneak alcohol past the WB gates. The studio brass came to the aide of their commodity, however, to help Flynn through a high-profile statutory rape case brought against the actor in 1942. He was acquitted in February 1943.

After The Master of Ballantrae (1953), Flynn left Warner Bros., a studio where he had made memorable pictures ranging from The Prince and the Pauper (1937), Footsteps in the Dark (1941), Never Say Goodbye (1946), Escape Me Never (1947) and Rocky Mountain (1950). He had been working with other studios since he was loaned out for That Forsyte Woman (1949) at MGM, where he also made the highly-successful Kim (1950), shot partially on location in India.

His star faded as his personal life became more unstable in the 1950s, though he released films like Against All Flags (1952), Mara Maru (1952), The Warriors (1955) and The Big Boodle (1957). He also ventured into television during the decade, hosting a short-lived British anthology series The Errol Flynn Theatre. 

Too Much, Too Soon found Errol Flynn coming face-to-face with his past, portraying his once-idol and friend John Barrymore in the biopic of Diana Barrymore. The movie details her struggles with alcoholism, a trait she shared with her famous father. Flynn, who was deep in his own issues with the disease, was a meta choice for the part, and he divided contemporary critics with his performance. The New York Times, however, offered glowing praise, writing, “Mr. Flynn steals the picture lock, stock and keg. It is only in the scenes of his savage disintegration, as the horrified girl looks on, that the picture approaches real tragedy.” When the real-life John Barrymore died in 1942, Raoul Walsh allegedly played a practical joke on Flynn by propping Barrymore’s fresh corpse, straight from the morgue, in a chair with a lit cigarette at Flynn’s house. The typically unflappable actor was scared out of his wits.

In the end, Flynn would succumb to the hard-living, hard-boozing lifestyle for which he, like Barrymore, was infamous. He was in Vancouver, B.C. to look at a yacht he was considering purchasing when he had a heart attack at age 50. The doctors who examined him said he had the physical ravages of a 75-year-old. He left behind two ex-wives, one then-wife and four children, including photojournalist Sean Flynn, who’s own life met a mysterious and tragic end when he was captured by communist guerrillas in Vietnam. His body was never found.

As tragic as Errol Flynn’s end might ring, his filmography largely stands the test of time, and his larger-than-life persona continues to attract new audiences.

My Wicked, Wicked Ways closes with the rather prophetic line, “The second half-century looms up, but I don’t feel the night coming on.”