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A dashing swashbuckler; a New Guinea plantation master; a drunk and opium fiend; a hero of the land and man of the sea; a published author; a man of action; a gentlemen and a Don Juan; a cowboy and a Castro sympathizer. From Australia through Hollywood and to Jamaica, Errol Flynn remains one of Hollywood’s greatest stars, and possibly, its greatest enigma.

Flynn was never bestowed any of Hollywood’s honors or awards, although his persona was an embodiment of the greatest asset a film star requires – charisma – of which he had an abundance. Flynn’s qualities as a film star were undeniable from his first starring role in CAPTAIN BLOOD (1935). His charisma often helped camouflage his limitations as an actor, and although his skills constantly improved, leading to a tour-de-force performance as John Barrymore in TOO MUCH, TOO SOON (1958), Flynn rarely embodied a character – the character embodied Flynn. Ironically, as his career deteriorated and his star faded, his performances became better and better.

Flynn’s virtues were many, but so were his vices. After a notorious statutory rape trial in 1943, in which he was acquitted, Flynn was stigmatized as an incorrigible ladies’ man, diverting any discussion of his film work to his sexual conquests, eventually consuming his life and career. Flynn may be the only actor with a phrase coined after him to describe a man’s sexual success – “In like Flynn.” This, unfortunately, still overshadows his achievements, leaving him a vastly underappreciated actor to this day.

The rape trial was a turning point in Flynn’s life and career, but problems with maintaining his public image began when he failed to join the war effort in WWII. He desperately wanted to enlist, and was rejected from every branch of the army he applied to. Flynn’s long health record, including tuberculosis and malaria, kept him from joining. He even wrote to the Office of Strategic Services, offering himself as a foreign diplomat. Regardless of his struggles to join, the public noticed the irony of Flynn, the great athlete and hero, staying at home while fellow actors like Clark Gable, James Stewart, and David Niven were fighting for their country.

Previously, Flynn had traveled to Spain as a Franco supporter during their civil war; later on he traveled to Cuba in support of Castro’s revolution; but his only way to participate in WWII was by raising the nations’ morale through cinema. The new TCM box-set, Errol Flynn Adventures, celebrates 5 of Flynn’s WWII films, allowing him to do something he so badly wanted to be doing in real life – killing Nazis.

Four of the five films in the TCM collection were directed by Raoul Walsh, who became Flynn’s signature director after the star parted ways with Michael Curtiz, who directed him in twelve films. Curtiz knew how to bring the dashing hero out of Flynn, whereas Walsh recognized the dualities inherent in Flynn’s persona. His dark sense of humor and melodramatic tendencies worked to incorporate melancholy even when Flynn was at his most charismatic.

In DESPERATE JOURNEY (1942) he certainly is at his most charismatic. When his plane is shot down over Germany, Flight Lt. Terry Forbes (Flynn) must lead his crew through enemy territory back to England. A fantastic story befitting an old Men’s Adventure Magazine, DESPERATE JOURNEY embraces and delights in its far-fetched plot. Walsh called it “a war comedy spiced with enough tragedy to give it reality.” The ensemble cast includes Ronald Reagan, Arthur Kennedy, and Alan Hale. They appear to have a genuine good time, roaming through Germany, beating the odds. The comedic tone doesn’t hurt the high suspense captured by the fast-paced plot, the striking black and white photography, and the beautiful Nancy Coleman as a German ally. Adventure films rarely get better than this.

Flynn’s rape scandal broke when DESPERATE JOURNEY was in release theatrically, but it didn’t hurt the box-office. During that time he was filming EDGE OF DARKNESS (1943). Directed by Lewis Milestone, it brings to screen the Norwegian resistance in WWII. Flynn plays a fisherman, the leader of the underground resistance in a small village, but he gets limited screen-time in what’s more of an ensemble film including Ann Sheridan, and Walter Huston.

EDGE OF DARKNESS tries hard to be important. The script features too many moments of high melodrama and over sentimentalism that’s not supported by its form. Even if the high aspirations of the filmmakers result in a flawed film, much could be said to its credit. Milestone directs the camera with incredible vitality, inventively utilizing dolly shots and zoom lenses to punctuate movements within the frame. The score, by Franz Waxman, beautifully compliments those movements, almost in dialog with them. Flynn and Sheridan, despite their uninspired performances, share wonderful screen chemistry, and Huston is worth watching in every scene he has ever done.

NORTHERN PURSUIT (1943) was the first film he shot after his statutory rape trial. Flynn stars as a Canadian Mountie trying to infiltrate a group of German spies on a mission in the Canadian mountains. Flynn seems bored with the material and with his female co-star, Julie Bishop. Raoul Walsh goes through the motions. The result is a mediocre vehicle for both. A bare-boned, slow-moving plot turns what starts as a promising snow adventure into a rather static affair. Conceived from the start as a quickie, NORTHERN PURSUIT would serve, at most, as a pleasant Sunday matinee.

When Flynn’s contract with Warner Brothers expired, he negotiated a new one that allowed him to choose his projects. UNCERTAIN GLORY (1944) was his first choice. Co-written by famed Western author, Max Brand, UNCERTAIN GLORY isn’t quite a WWII film as much as a Film Noir set against the backdrop of Nazi occupied France. Flynn portrays French criminal Jean Picard, condemned to die by the guillotine for the crime of murder. Preferring death by a firing squad, Picard offers Inspector Marcel Bonet (Paul Lukas) to hand himself over to the Gestapo, pretending to be a wanted saboteur, saving the lives of a 100 men the Germans threaten to kill unless the saboteur is brought to justice. Reluctant to turn himself in and become a martyr, Picard tries to escape at every given chance.

Flynn’s performance is sincere even when he lies. He plays Picard with conviction, and with a melancholic quality that characterizes his best performances. Beyond the façade of the dashing hero appears a thinking man, sometimes a broken one – an enigma not just to those around him but also to himself. Picard remains one of Flynn’s most interesting and personal performances.

The final collaboration between Flynn and Walsh, OBJECTIVE, BURMA! (1945), is an unsung masterpiece. A war picture, ahead of its time, that should be celebrated alongside other classics. Flynn heads a group of paratroopers who find themselves stranded in the Japanese-occupied Burmese jungle. With few supplies, they face a long walk back to safety. Flynn’s performance is restrained and powerful, starting off as a charismatic leader, progressing to a man who sees his friends butchered by the Japanese, struggling to keep his composure. One of his personal favorites, he’s truly at his best.

OBJECTIVE, BURMA! is uncharacteristically gritty and unrelenting, offering a glimpse into the miserable state of men in war. To achieve a realistic look, Walsh decided to shoot it on location, versus on a studio set, filming in swamps around Orange County. The photography, by the great James Wong Howe, is reminiscent of the period’s newsreels, never beautifying or highlighting the actors, giving the film a documentary atmosphere (Walsh also incorporated newsreel footage within the film). The score, by Franz Waxman, achieves a lot by resorting to minimalism. As the men venture through the jungle the score remains a low, suspenseful, undertone. Instead of bathing in glorifying music, Walsh thrusts heavily in terrifying silence. In terms of form, OBJECTIVE, BURMA! almost serves as an anti-war film considering the genre’s conventions in the 1940s.

Still, OBJECTIVE, BURMA! was made during the war as a tool of Hollywood propaganda. It had to comply with certain demands to raise morale, bookending it with positive affirmations to make it heroic. But Walsh intelligently subverts this notion. In the end, when Flynn is congratulated for a successful mission, he hands his commander a stack of dog tags belonging to the men he lost. “Here’s what it cost,” he tells him. The men’s lives become nothing more than currency. Walsh asserts his grim point of view about the film industry, that “war does many things besides killing a lot of people. It can make instant millionaires out of struggling businessman.”

OBJECTIVE, BURMA! opened in Britain and closed within a week. Severely criticized for its depiction of the Americans winning Burma, when the invasion was predominantly British. It is understandable how at the time, with tensions high, such matters would be highly offensive. In retrospect, we should treat Hollywood war epics not as a depiction of history, but as historical fiction. In his autobiography, My Wicked, Wicked Ways, Flynn remembers a later meeting with the King George VI. The British monarch inquired why people laugh about Flynn every time Burma is mentioned. “Sir,” responded Flynn. “Apparently the picture proved conclusively that I took Burma singlehanded and it was a pushover, sir.” This is Flynn’s war, and he’s winning.