The Absolute Best Pirate Films - Rooftop Cinema Club

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The Absolute Best Pirate Films

When you think about it, Pirates are kind of the astronauts of the sea. They definitely deserve some love, so we’re taking a dive into the deep blue to explore some of our favorite pirate movies (and yes, we’re throwing some Pirates of the Caribbean in the mix, but only the first three. Ain’t nobody got time [nor watched?] all five of those films). So please make sure your sword is securely fastened in your…whatever that belt thing is that pirates wear…and enjoy the dive.

HOOK (1991)

Pros:

Ummmm –
1. Captain Hook’s Mustache
2. Robin Williams. Biggest pro here.
3. This was the OG live-action of Peter Pan, and it’s a classic.
4. Steven Spielberg made this thang
5. And John Williams made the music to this thang

‘Nuff said, drop the mic.

Cons:

If you’re too young/old to have grown up with this film. That’s the con. Because that’s a damn shame.

Favorite Quote:

“To live would be an awfully big adventure.”

hook

PIRATES OF THE CARIBBEAN: THE CURSE OF THE BLACK PEARL (2003)

Pros:

Let’s make one thing clear here: when it comes to pirates, it’s pretty tough to find one as witty (and as sexy) as Jack Sparrow. He’s enough of a pro, but another thing worth mentioning is that this is the orig POTC and seriously set the bar high for the future sequels.

Cons:

The envy that comes from wishing you got to film an entire movie with Johnny Depp and Orlando Bloom. And Keira Knightley…SWOON!

Favorite Quote:

“But why is the rum gone?!?”

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THE PRINCESS BRIDE (1987)

Pros:

I mean, there are so many; this movie is iconic. But without a doubt, Dread Pirate Roberts’ costume is the best (and even comical). If Zorro was crossed with Sniper from Dora the Explorer, you’d get Dread Pirate Roberts.

Cons:

Yet another tale of Pirates being made out to be the villains. Sigh.

Favorite Quote:

“INCONCEIVABLE.”
“You keep using that word. I do not think it means what you think it means.”

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PIRATES OF THE CARIBBEAN: DEAD MAN’S CHEST (2006)

Pros:

#1: Just how incredible the CGI was at the time for the creation of Davy Jones.
#2: This gif of Jack running.

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#3: That badass crazy voodoo queen (Sea Goddess Calypso, to be polite)! MORE. OF. HER.

Cons:

The nightmares that came from seeing octopus-head Davy Jones.

Favorite Quote:

“I’ve got a jar of dirt, I’ve got a jar of dirt.”

slimey

THE GOONIES (1985)

Pros:

The adventure, the pirate ship, and the best part of being a pirate: a map where X marks the spot (I mean, try and tell us that doesn’t sound fun to you. A treasure hunt?! Yes please).

Cons:

One does not simply ‘find cons for The Goonies’.

Favorite Quote:

“Goonies never say ‘die’!”

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PIRATES OF THE CARIBBEAN: AT WORLD’S END (2007)

Pros:

(SPOILER ALERT) When we’re introduced to Jack Sparrow’s dad. And what’s even better: he’s played by Keith Richards of The Rolling Stones. There was just a lot of glory in the unveiling of that character, okay? #DILF

Also, this even better gif of Jack running:

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Cons:

Trying to figure out what just happened for the past 2 hours and 49 minutes. Also the fact that the movie is 2 hours and 49 minutes.

Favorite Quote:

“It’s not just about living forever, Jackie. The trick is still living with yourself forever.”

Pirates-of-the-Caribbean-5-cast-includes-Keith-Richards

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