Images of sailing adorn popular life here in America, but not because lots of us actually sail – in fact, it’s quite the opposite. Jewelry, fashion, and financial companies – or rather, their advertising agencies – bank on yachting’s perceived exclusivity to sell their high-dollar wares. Yachts are featured as bit players in film, too; hundreds of them, but rarely does sailing play a big part in the story. But sometimes it does, and since we can’t find any article that’s ever given a ‘best of sailing movies’ review, we decided it was our duty to do just that.
But who’s got time to research the best movies to watch? No one. So we decided to do the heavy lifting for you, and along with a few forum members, we came up with the official Sailing Anarchy Top Ten Sailing Movies Of All Time. We tried to restrict these to full-length feature fiction or documentary films, and we left off pretty much everything from the olden days; those swashbuckling films may look good in your memory, but with very few exceptions they didn’t age well at all. You can find most of these on Amazon or Netflix or the various BitTorrent or Free TV Search Sites out there, and feel free to tell us what we missed in the thread.
10 – Morning Light
Take a pile of young sailors, give them a shit hot TP-52 and some of the best coaches in the world to train them to race it, and send them on a race to Hawaii. Throw in a custom-modified power trimaran to follow them every step of the way, and you’ve got the recipe for the ultimate sailing movie. Right? Somehow, it didn’t’ work out that way. This could’ve been Roy Disney’s final and most enduring legacy to a sport he adored, but it fell flat in almost every way: The race itself was a dull one, they didn’t even end up being the youngest team in the race, and somehow, the editing team managed to make some damned interesting and opinionated kids look downright dull. They had hours and hours and hours of gates-of-hell style sailing off Hawaii during training, tons of shots of fights and drama and the real stories about a crew having to come together to win, yet somehow, none of that made it to the final cut after an editing process frought with disagreement and delay. Morning Light makes it to the Top Ten solely on the strength of the offshore training footage – it’s by far the best-produced big-water sailing footage of a modern racing boat available. On a big screen, you tend to fast-forward through the rest of it.
9 – 180 South: Conquerors of the Useless
This recent feature doco contains maybe the least amount of sailing of any of these Top Ten pictures, and most of it is over and done with before the first half of the documentary. But that bit includes a very real and quietly beautiful piece of ocean passagemaking from the US to the South Pacific that is an absolute must-see piece for any ocean sailor, combined with more reality with a dramatic dismasting and the month-long jury rigging process on wild Rapa Nui (Easter Island), followed by the eventual landing in Chile. Once in Patagonia, Jeff Johnson meets up with Yvon Chouinard and Doug Tompkins; the conservationist heroes who helped tell the world about this most wild of places nearly 50 years ago. Whether you’re surfer, sailor, scientist, climber, or just a kid, the haunting beauty and incredible video work in a place that can easily overwhelm the lens is some of the best you’ll ever see. And the conservationist message is powerful without being preachy, thanks to Johnson’s Warren Miller-esque narration and a script that’s more surf movie than Discovery channel. A great one for kids and adults alike, and one you can turn schoolteachers onto as well if you want to see the next generation conserving more than this one.
8 – Dead Calm
A young Nicole Kidman shows off her tits and ass, then later has a wheel in one hand and a spear gun (or was it a flare gun) in the other, kicking ass and taking names. At least that’s how we remember it, so do we really need to go into the plot? There’s plenty of suspense, but the movie loses sailors with some of its seaborne silliness, and loses regular folk with the stupidity of its main characters. Billy Zane plays a pretty good maniac, while Sam Neill is the useless foil to Kidman’s badassery. But Kidman’s flesh and her expressiveness are the real stars, and no matter how dumb the plot, she makes you want to cheer for her as she opens up a can of beatdown up on Zane.
Bonus Fact: The movie was shot mostly just off Hamilton Island, Australia – the site, of course, of the famous Hamilton Island Race Week. Kidman’s “Saracen” was actually the Van De Stadt 73’ plywood ketch “StormVogel”, which won the Sydney Hobart in 1965 and is still racing today. Bonus Rumor: A pair of Kidman’s panties still hangs in the stateroom of StormVogel.
7 – Pirates of the Caribbean
Yes, the sailing is ridiculous. But the movie – if you can remember back to before it was a billion-dollar franchise wiuth a litany of crappy sequels and merchandise overload – was a roller-coaster ride of fun and adventure that brought swashbucklers into the 21st century. This one makes the list for its sheer enjoyment value, as well as for the interest it created in tall ships for literally hundreds of millions of kids around the world.
6 – White Squall
One of the true classics for the thousands of kids and adults that have gone through some form of tall ship training, this pic casts a flawless Jeff Bridges as Skipper Chris Sheldon of the Brigantine Albatross in 1962 – a sail training/university ship for well-off kids long before such a thing became accepted. Directed by visionary director Ridley Scott, the script was written using many of the actual documents produced during the maritime hearings from the real-life tragic loss of the brig, which took four students’ lives along with those of the cook and Sheldon’s wife. This one is worth watching for anyone, but the capsize and sinking scene gives sailors a particularly harrowing look at all of our biggest fear: Being trapped in a sinking boat. Bonus Fact: Captain Sheldon went into the Peace Corps after losing the Albatross, and in 1965 he bought another ship – she burned to the waterline off West Africa on only her second voyage, and Sheldon would never return to sea. Bonus Education: Daniel S. Parrott spent years researching the loss of the Albatross along with those of four other tall ships, and carefully pieced together the very simple explanation for why these boats were inherently dangerous in the 2002 book Tall Ships Down. An excellent read after watching the movie.
5 – Master and Commander: The Far Side of the World
Bringing one of every bored cruiser’s favorite seafaring characters to the big screen, director Peter Weir brought in a great cast and spent some serious money making brutally believable battle and storm scenes from the Age of Sail. It’s a combination of a couple of books from Patrick O’Brians epic series, and the great characters and detailed realism of the chases and skirmishes at sea help the movie appeal to a broad audience, both lubbers and salts. An enjoyable movie on every level, and easily watchable more than once. Bonus Fact: Weir hired longtime SA’ers to teach Russell Crowe and other crew how to handle lines properly and to safely climb the rigging of a tall ship at their base in Baja California.
4 – Masquerade
Rob Lowe is a studly young rockstar skipper running loaded old FBO Brian Davies’ S&S 70’ Mini-Maxi “Obsession” for the summer out of the Hamptons. He’s also running Davies’ trophy wife (a Kim Catrall already the slutty older women back in ’88!) around the bedroom, but he falls in love with a very young and exceptionally cute Meg Tilly instead. To complicate matters, someone is trying to steal Tilly’s massive fortune, Lowe is blowing hundreds of thousands on modifications to the boat, the cops are dirty, and the propane isn’t the only thing that’s explosive. This is a fun thriller with lots of sailing, most of it – including some of the sailor stereotypes – being quite accurate. And don’t even think that you sounded any cooler than the douchebag yachties in this 80’s classic. Viewing Tip: This one will hold the attention of a non-sailing wife. Bonus Fact: The hull of the Hinckley 36 used as “Masquerade” in the production was, according to a Hinckley Company newsletter, in good shape after they blew her up in a ball of fire. She was acquired by an experienced boatbuilder to be subsequently restored. Where Are They Now: At least a couple of years ago, Obsession was still doing head boat daysails out of Seattle’s waterfront.
3 – Deep Water
This one is deep indeed, and painful too, and it asks all the right questions about the first solo offshore racer to truly step into the void. The 93-minute documentary about Donald Crowhurst’s infamous leap into the chaos of the first non-stop, Round-The-World race relies on riveting footage found aboard the ghost ship Teignmouth Electron months after Crowhurst disappeared along with words and video from Moitissier and Sir Robin. The film documents Crowhurst’s descent into madness, and the reasons it was almost a foregone conclusion. Filmmakers Louise Osmond and Jerry Rothwell force all seafarers to ask themselves some of the deeper questions behind our own motivations for escaping a land-bound life, be it for a few hours or a few years.
2 – Captain Ron
We’ll always love this one for its unending stream of memorable quotes, combined with just how hilariously true all the delivery skipper stereotypes seem to be when seen through a comic director’s eyes. Kurt Russell fits the bill perfectly, with Martin Short as the clueless owner and a hilarious crew keeps it interesting, and if you haven’t seen it in a while, medicate yourself with your favorite elixir and sit back for an hour and change of laughs.
1 – Wind
Still the gold standard by which all other crappy sailing movies are judged, Wind succeeds for sailors because a) it’s our only real ‘sports/drama’ movie and it loosely follows the reality from 1983 to 1987, and b) because of the utter ridiculousness spewed in nearly every scene. From the sail that goes “Whomp” to the pickup truck/salt flat wind tunnel tests to the stupid Geronimo dance, it keeps you laughing even as you check out Jennifer Grey’s sailor chick credentials. We don’t need no stinkin’ rules for yacht racing, do we? Not when it goes from flat calm to ocean gale in the middle of a single buoy race! For all of its substantial stupidity, Wind was still the first movie to really capture some of the excitement of sailing that Hollywood’s ever seen; the 14-foot skiff (a/k/a I-14) footage is breathtaking, and some of the AC racing scenes in the big stuff will be remembered forever. And as long as we keep it alive for the next generation, there will be Whompers in the sail locker for another 50 years. Bonus Fact: Iconic lifetime yachting commentator Peter Montgomery does most of the ‘TV commentary” in the movie.