Five Most Charming Film & TV Robin Hoods: An Extremely Subjective List

Just to be clear right from the get go — this is not a list of the most historically accurate Robin Hoods. It’s not about which adaptation stays truest to the medieval ballads and historic fashion trends. It’s not about the most flawlessly plotted storylines. And it’s most certainly not about grittiness, realism, or how much blood is caked onto the hero’s blade. (Which I know was the reality of Medieval England … but that’s a lot less fun to dream about, now isn't it?)

You can keep your joyless Russell Crowe. You can keep your witless Patrick Bergin. I recently saw the trailer for the Death of Robin Hood … and Hugh, you make a pretty great Wolverine, but you are not my outlaw of choice.

This is about charm.

Robin Hood, at his core, must be a charming trickster. If he can’t win you over with a grin before he robs you, the spirit of the legend is lost … and so is my attention span.

So here we go —

5. Kevin Costner – Robin Hood: Prince of Thieves (1991)

To be honest, I struggled with this slot the most. It almost went to Richard Greene, who is arguably the superior Robin. But I am a child of the ’80s, and nostalgia is a powerful force.

Robin Hood: Prince of Thieves was my gateway outlaw. (Fine. The Fox was technically first. We’ll get there.) And despite Costner’s heroic commitment to not attempting a British accent — and yes, I heard the Cary Elwes joke in my head as I wrote that — this version made it’s mark on my heart. On my soul… (Crap. Now the song’s in my head.)

If I’m honest, it may have been Mary Elizabeth Mastrantonio’s Marian that captured my young heart more than Costner’s Robin. Still, nostalgia counts for something.

According to Roger Ebert, the film was “a murky, unfocused, violent, and depressing version of the classic story…”

Which I find fascinating, because adaptations have largely grown murkier and more depressing since 1991. (And that is precisely what I am endeavoring to rectify with Hoodwinked, by the way.)

4. Jonas Armstrong – BBC’s Robin Hood (2006-2009)

Remember: this is not about plot. Or realism. Or … seriously, what the heck were they wearing?

This is about charm.

Jonas Armstrong delivers exactly what I want — a playful, mischievous, slightly irreverent trickster, harkening back to the earliest ballads. He smiles. He banters. He seems to enjoy himself.

That enjoyment matters. And it should always feel like Robin is in on the joke.

3. The Fox – Disney’s Robin Hood (1973)

Don’t look at me like that.

I said charming, not “most ruggedly attractive outlaw.” I am not a weirdo.

But if you were born before 1990 and someone says the name “Robin Hood,” tell me this isn’t the first image that pops into your mind.

Anthropomorphizing the characters was genius. The fox is clever, honorable, warm, and unusually self-aware for a children’s cartoon character. He is the perfect animal embodiment of the legend.

And yes. My first crush may have been animated and orange. I refuse to be shamed.

2. Cary Elwes – Robin Hood: Men in Tights (1993)

What can I say? I like to laugh.

This movie has played in the background of my life for decades. I’ve seen it dozens of times. I still grin when he delivers a line with that perfectly arched eyebrow.

Yes, it’s a spoof — largely of Prince of Thieves — but it also lovingly nods to The Adventures of Robin Hood. Elwes is very clearly channeling Errol Flynn, and he does it brilliantly.

He updates the charm without losing the swashbuckling spirit. (Plus he’s kinda cute.)

1. Errol Flynn – The Adventures of Robin Hood (1938)

Terrible haircut. Ridiculous costumes. Completely perfect.

Errol Flynn is the G.O.A.T.

When Flynn laughs, I smile. Sometimes I laugh right along with him. His natural charisma — the very thing he was legendary for — makes him the quintessential Robin Hood.

He’s bold without being broody. Heroic without being humorless. Daring without being dour.

He is, quite simply, charming.

And if Robin Hood isn’t charming… then he’s not Robin Hood.

Honorable Mention:

Douglas Fairbanks – Robin Hood (1922)

I feel morally obligated to nod to the original silver-screen outlaw. But alas, I need to hear the wit to fully surrender my heart. Silent films require a level of cinematic appreciation that is above my head.

However, delightful trivia: the film’s scenario editor was Lotta Woods.

Lotta Woods.

If that is not the most perfect name for someone working on a Robin Hood movie, I don’t know what is. I’m kinda reconsidering my own pen name.

And there you have it. An unapologetically subjective ranking of the most charming Robin Hoods

ever to don Lincoln green.

Charm first.Blood and guts later. Or never. That’s cool too.