The Princess Bride (1987) movie poster

The Princess Bride

1987

5 / 5

Director Rob Reiner

Cast Cary Elwes, Robin Wright, Mandy Patinkin, Chris Sarandon, Wallace Shawn & more

  • fantasy
  • romance
  • comedy
  • adventure
  • classic
  • quotable

↩ Would Watch Again

A perfect blend of fantasy, romance, adventure, comedy and revenge. The Princess Bride should not work on paper, which is exactly why it works so well. Every time I watch it, it is still effortlessly entertaining.

Synopsis

A farm boy falls in love with a princess.

The princess is kidnapped.

A giant, a swordsman and a criminal mastermind get involved.

There are sword fights, revenge plots, poisonings, kidnappings, miracles and unusually large rodents.

Or, put another way:

A straightforward project rapidly expands beyond its original scope and somehow becomes one of the most beloved films ever made.

What I Expected

I honestly cannot remember the first time I watched The Princess Bride.

It’s simply always been there.

Like Star Wars.

Like Monty Python.

Like that one server nobody knows who built but everyone is terrified to switch off.

I’ve watched it countless times over the years and every time I put it on, I know exactly what’s coming.

The jokes.

The sword fights.

The quotes.

The characters.

And yet somehow I still enjoy every minute of it.

What I Got

Perfection.

Not technical perfection.

Not cinematic perfection.

Just pure entertainment perfection.

The Princess Bride is one of those rare films that understands exactly what it wants to be.

It does not try to be clever.

It does not try to launch a cinematic universe.

It does not spend half its runtime setting up six sequels.

It simply tells a story.

And tells it brilliantly.

Review

Where do you even start?

The cast is exceptional.

Cary Elwes is perfect as Westley.

Robin Wright is excellent as Buttercup.

Mandy Patinkin delivers one of the most iconic revenge arcs in film history.

And then there’s Andre the Giant.

Fezzik remains one of my favourite characters in any film.

His problem-solving methodology can best be described as:

Apply additional force until the issue disappears.

A strategy still widely used in enterprise IT.

The sword fight between Westley and Inigo Montoya remains one of the greatest scenes ever filmed.

Not because it’s realistic.

Not because it’s particularly violent.

Because it’s fun.

Something modern films often forget.

The dialogue is endlessly quotable.

Every character is memorable.

Every scene serves a purpose.

Even the smallest roles leave an impression.

The film somehow manages to combine:

  • Fantasy
  • Romance
  • Adventure
  • Comedy
  • Action
  • Revenge

And makes all of it work.

On paper, this should not be possible.

Any architecture review board would reject this concept immediately.

Requirements unclear.

Scope excessive.

Success criteria undefined.

Yet somehow every component fits together perfectly.

Security Assessment

As a Security and Identity Architect, I feel obligated to point out several significant concerns.

Identity verification appears non-existent.

Westley is believed dead.

Westley returns.

Westley spends a significant portion of the film wearing a mask.

Nobody performs identity validation.

No MFA.

No Conditional Access.

No Authentication Context.

Nothing.

The Dread Pirate Roberts repeatedly bypasses physical security controls with alarming ease.

Prince Humperdinck demonstrates all the classic indicators of an insider threat.

Excessive privilege.

No oversight.

Questionable decision making.

And a complete disregard for governance.

Meanwhile Vizzini’s security strategy appears to rely entirely on believing he is smarter than everyone else.

This proves unsuccessful.

Enterprise Architecture Assessment

The Princess Bride should not work.

That is what makes it brilliant.

This is the startup that succeeded despite every consultant advising against it.

No governance framework.

No steering committee.

No change control board.

No operating model.

Just a talented team with a clear vision executing brilliantly.

Sometimes organisations spend years building governance structures designed to guarantee success.

The Princess Bride demonstrates something equally important.

Success still requires creativity.

Heart.

Character.

And people who understand the product they’re building.

Final Verdict

I’ve lost count of how many times I’ve watched The Princess Bride.

I’ve watched it as a child.

I’ve watched it as an adult.

I’ve watched it when I wanted something familiar.

I’ve watched it when I wanted something funny.

And I’ve never once regretted pressing play.

The jokes still land.

The characters still work.

The story still entertains.

And somehow it remains just as enjoyable today as it was decades ago.

Very few films achieve that.

Even fewer make it look effortless.

Completely Unqualified Verdict

Hello.

My name is Inigo Montoya.

You killed my father.

Prepare to cry when he finally gets his revenge.

Scorecard

Story: 5/5

Acting: 5/5

Comedy: 5/5

Sword Fighting: 5/5

Quotability: Inconceivable/5

Insider Threat Detection: 0/5

Andre the Giant Solving Problems: 5/5

Would Recommend: 5/5

Likelihood of Watching Again: Absolutely

Overall: 5/5

Scorecard

Story
5 / 5
Acting
5 / 5
Comedy
5 / 5
Sword Fighting
5 / 5
Quotability
5 / 5
Insider Threat Detection
0 / 5
Andre the Giant Solving Problems
5 / 5
Would Recommend
5 / 5
Overall 5 / 5

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