Errol Flynn was the original Hollywood bad boy. Long before the tabloids were obsessed with modern stars, Flynn was living a life that made his onscreen sword-fighting look like a Sunday school picnic. If you’ve ever looked for the My Wicked, Wicked Ways movie, you’ve likely stumbled upon the 1985 made-for-TV biopic technically titled My Wicked, Wicked Ways: The Legend of Errol Flynn. It’s a wild ride. Honestly, trying to cram Flynn’s entire autobiography into a television movie is a bit like trying to fit the Pacific Ocean into a thimble. It's messy. It’s loud. It’s occasionally very, very problematic.
But it works because Flynn himself was a walking contradiction.
The film stars Duncan Regehr as the swashbuckling icon. Now, Regehr had the look. He had the mustache. He had that specific brand of arrogant charm that Flynn weaponized during the Golden Age of cinema. The movie basically tracks Flynn’s meteoric rise from a rough-and-tumble drifter in New Guinea to the king of the Warner Bros. backlot. It’s based on Flynn’s own posthumous memoir, which—let’s be real—was probably 40% exaggeration and 60% drunken honesty.
The Reality Behind the My Wicked, Wicked Ways Movie
People forget that Errol Flynn wasn't just a guy who looked good in green tights. He was a disaster. A beautiful, charismatic, self-destructive disaster. The My Wicked, Wicked Ways movie tries to capture that tension between the man the public loved and the man his friends feared for.
Think about the context of 1985 television. You couldn't show everything. Flynn’s book is notoriously graphic for its time, detailing his sexual exploits, his opium use, and his general disdain for authority. The movie has to dance around some of the darker corners. It focuses heavily on his relationship with his father, his tumultuous marriage to Lili Damita—played with a wonderful sort of frantic energy by Barbara Hershey—and his legendary friendship with David Niven.
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Is it 100% accurate? No way.
Biopics rarely are, especially ones made for CBS in the eighties. But it captures the vibe. It captures that sense of "live fast, die young, and leave a scarred corpse" that defined Flynn’s philosophy.
Why Errol Flynn Still Matters in 2026
You might wonder why we are still talking about a 40-year-old TV movie about a guy who died in 1959. It’s simple. Flynn was the blueprint. Every "troubled" male lead we see today owes a debt to the template Flynn created. He was the first to prove that you could be a massive jerk behind the scenes and as long as you could fence and flash a crooked grin, the world would forgive you. Until they didn't.
The movie shows the cracks.
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It shows the moment the drinking starts to take its toll. It shows the exhaustion of being "Errol Flynn" 24 hours a day. Honestly, it’s a cautionary tale disguised as a glamorous adventure. If you watch it today, you see the shadows of the "Me Too" era looming over his legendary "in like Flynn" reputation. It’s a difficult watch through a modern lens, but that’s exactly why it’s worth discussing. We have to look at how we used to mythologize men who were, by all accounts, pretty toxic.
Production Hustle and 80s Glamour
The filming of the My Wicked, Wicked Ways movie wasn't exactly a smooth sailing adventure like The Sea Hawk. They filmed in various locations to mimic the tropical heat of Flynn's early years. The costumes are actually one of the highlights. They got the high-waisted trousers and the slicked-back hair just right. It feels like a time capsule.
Interestingly, the film features Hal Holbrook as Bill Morrison, a character who acts as a sort of moral compass or narrator for Flynn's chaos. It’s a necessary anchor. Without a "normal" person to react to Flynn, the movie would just be a series of parties and fistfights.
- Duncan Regehr didn't just play Flynn; he channeled the exhaustion.
- The cinematography leans heavily into that soft-focus 80s glow.
- It covers the 1942 statutory rape trial, which was the beginning of the end for Flynn’s career.
That trial is the pivot point of the story. It’s where the "wicked ways" stop being charming and start being criminal. The film handles it with the sensibilities of the 80s, which is to say, it’s a bit glossed over compared to how a modern HBO miniseries would handle it. But the weight of it is there. You see the public's perception shift in real-time.
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How to Watch and What to Look For
Finding the My Wicked, Wicked Ways movie today can be a bit of a treasure hunt. It pops up on YouTube in grainy quality or on specialized classic film streaming services. If you do find it, don't expect a 4K masterpiece. Expect a gritty, somewhat melodramatic look at a man who was his own worst enemy.
Pay attention to the scenes between Flynn and his father. Those are the most "human" moments in the film. They strip away the "Robin Hood" persona and show a boy who just wanted approval. It’s a classic trope, sure, but in Flynn’s case, it feels earned. His father was a respected scientist, and Errol was... well, Errol.
Actionable Takeaways for Film Buffs
If you're diving into the world of Errol Flynn or looking to understand why this specific movie exists, here is how to approach it:
- Read the book first. The movie is a sketch; the autobiography is a vibrant, terrifying painting. Flynn’s writing is surprisingly sharp and self-aware.
- Compare it to The Last of Robin Hood. This is the 2013 film starring Kevin Kline as an aging Flynn. Watching both gives you the full arc—from the rising star in My Wicked, Wicked Ways to the tragic, fading figure at the end of his life.
- Check the sources. Look into the memoirs of David Niven (The Moon's a Balloon). Niven provides a much more grounded perspective on what it was like to actually live with Flynn during their "Cirrhosis-by-the-Sea" days.
- Analyze the "Bad Boy" Trope. Use the film as a case study. Notice how the narrative shifts from celebrating his rebellion to mourning his waste of talent.
The legacy of the My Wicked, Wicked Ways movie isn't just about the acting or the 80s production value. It's about the enduring fascination with people who refuse to play by the rules, even when those rules are there to keep them alive. Errol Flynn lived several lifetimes in his 50 years. This movie is just one small window into that beautiful, tragic mess.
To truly understand the impact of the film, you have to look at the transition of Hollywood. We went from the studio system "cleaning up" star images to movies like this that finally started to pull back the curtain. It wasn't the full truth, but it was a start. It showed that the man behind the mask was far more interesting—and far more broken—than the heroes he played on screen.