Cinematical Rewind: Ye WORST Pirate Movies Ever Made! (Arrr...)

By Scott Weinberg, Reprinted from July '06

You'll no doubt remember all the controversy and skepticism that surrounded the production of Pirates of the Caribbean: The Curse of the Black Pearl... Oh wait, maybe you wouldn't remember it -- because it existed only in the deepest realms of mega-movie-geekery. Much of the skepticism and dismissive chit-chat came from the fact that the movie was based on an amusement park ride ... but the astute movie nuts knew what the problem was:

There hadn't been a good pirate movie in about three decades, and we had no reason to think that trend was about to be bucked. I know what I'm talking about, because I was one of the hand-wringers, one of the oh-so-brilliant movie nerds who knew that any sort of pirate movie was doomed from the word go. (Needless to say, in the case of The Black Pearl, I was dead wrong, and I was extremely thrilled to admit how wrong I was.)

So with Pirates of the Caribbean: Dead Man's Chest only a few days away (and AWESOME!), I thought it might be fun to dredge back over the past few decades and dig up some of the gold-plated mega-turkeys that managed to keep the pirate genre buried at sea.

7. Yellowbeard (1983) -- The flick gets a break because it's a comedy and it comes packing one helluva cast list, but really: One should expect more than a few stray chuckles from a pirate farce that features Graham Chapman, John Cleese, Eric Idle, Madeline Kahn, Peter Boyle, Peter Cook, Marty Feldman, James Mason, Kenneth Mars, Spike Milligan AND Cheech & Chong! Those who still hold some fond Yellowbeard memories may be pleased to know that the DVD just hit shelves, but they might be better served by skipping a revisit and just holding onto those fond memories.

6. The Pirate Movie (1982) -- It must have seemed a brilliant idea at the time: A youthful re-imagining of The Pirates of Penzance, complete with the combined power of Kristy McNichol & Christopher Atkins, a bunch of outrageously atrocious pop tunes, and a trasure chest full of leaden pop culture references and lame-ass movie gags. I distinctly remember enjoying this movie as a know-nothing 12-year-old movie nerdlet (yep, I even owned the soundtrack cassette, lord help me), but a recent revisit with the flick (thanks a LOT, Anchor Bay!) only managed to give me one of those really painful ice cream-style headaches, served with a chaser of sickening nostalgia. The plot is beyond comprehension; the tunes are beyond terrible; the acting is ... hell, just rent the thing, but be sure to have a little weed handy.

5. The Island (1980) -- Once upon a time a man called Peter Benchley wrote a rather simplistic novel called Jaws, which was made into a film that not only improved upon its pulpy source material, but pretty much decimated the book all over the place. Following the success of that book/movie, Mr. Benchley got to give us two more flicks: The Jacqueline Bisset jiggler known as The Deep -- and the stunningly nasty Michael Caine adventure flick The Island. It's about a gang of ferociously unpleasant buccaneers who have somehow avoided extinction, popping out of their hidey hole only to rape, kill, and plunder when necessity calls for it. (Yes, in modern times. Well, if 1980 is "modern.") The flick's even stupider than it sounds, but it's also true Guilty Pleasure material -- what with all the horrific violence and the he-man Michael Caine and the always awesomely villainous David Warner... (There's probably a good reason Paramount won't dust this one off for DVD treatment already.)

4. Treasure Planet (2002) -- I'm simply of the opinion that Disney animation and pirates don't really go together. And then you throw the whole thing into outer space... Another ice cream-style headache, despite the admittedly pretty animation.

3. Nate and Hayes (1983) -- Here's another one I had very old and very fond HBO memories of, but a recent DVD release cured THAT fandom real fast. A grungy-looking and entirely unconvincing high seas adventure packed with plaster sets, cardboard scripting, wooden acting, and tons of derring-don't. Tommy Lee Jones looks positively embarrassed throughout the mess, while co-star Michael O'Keefe looks as reliably clueless as ever. Co-screenwriter John Hughes would move on to better things before dropping off the face of the planet.

2. Pirates (1986) -- I saw this movie on opening night: Leo Mall Twin Theater, 2/28/86. I think there were maybe 25 people in the whole audience. My memories of the flick are foggy, at best, but I do remember that Walter Matthau played a drunk, semi-shaven bear who wore a pirate hat and desperately wanted to get his hands on a throne made of solid gold. Directed by Roman Polanski (seven years after Tess and right before Frantic), the flick sank like a freakin' stone the world over. Me, I'd just like to see the thing get a DVD release already. The flick could turn out to be an overlooked mini-masterpiece -- or, more likely, it's just hilariously bad, which is even better. (Either way, it's got that really hot girl from The Golden Child in it.)

1. Cutthroat Island (1995) -- Points for trying to ressurect the genre, but after an approximate expense of $100 million and an approximate gross of $10 million, this flick did a whole lot more harm than good. Following this debacle, the mere mention of the words "pirate" and "movie" in the same sentence were enough to get a producer banned from Hollywood forever. In what might be the limpest tentpole cast ever assembled, Geena Davis and Matthew Modine sail away from Frank Langella. Often. Given my affection for the pirate genre, I'm semi-tempted to give this flick another run-through. But it'd just sit in my Netflix queue for the next 5 years, perpetually being bumped down by titles like Cannibal Zombie Death Shack and Hellraiser Part 16: Hellisher. (Then again, Roger Ebert gave Cutthroat Island 3 stars, so into the queue it goes.)

(Films considered for the list, but dismissed for various and obvious reasons: Cabin Boy (1994), Captain Lust and the Pirate Women (1977), Captain Ron (1992), Hook (1991), The Ice Pirates (1984), Pirates of Silicon Valley (1999), Pirates of the Plain (1999), Six Days Seven Nights (1998), and Sky Pirates (1986). I also meant to give careful research to this title, but, oddly, I kept nodding off after only one or two scenes.)