Here then, is a guide for the collector, a chronological overview of the essentials, optionals, and avoidables. (What's not here, for space reasons, are pirate-oriented comedies, musicals, TV series, cheap direct-to-disc knockoffs, cartoons, or any other strictly kiddie-matinee fare).
The Black Pirate (1926) You see a silent movie in color and instantly think, "those pesky colorizers, desecrating a classic with their high-tech Crayolas." But no, this seminal genre gem actually was shot in a very early Technicolor process; to a 1920s audience it must have seemed quite an extravagant visual feast. The prototype of the movie swashbuckler, Douglas Fairbanks grins, cavorts, leaps about, and sets the template here for much of what will follow in years to come; some stunts that originated in this old chestnut still get ripped off from time to time. The ship looks ridiculously fake - more like some sort of stylized playground edifice - and the swordplay comes off like just a bunch of frenzied flailing. But a genuine high-spiritedness pervades The Black Pirate.
Kino's DVD is a loving restoration, with a clean image (considering the film's antique vintage), the original music score replicated, and a host of worthwhile special features. The movie's entertainment value has grown somewhat creaky, but its historic importance is unassailable.
Three skull & crossbones. More for the serious collector than casual viewer.
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Treasure Island (1934) A fine rendering of Robert Louis Stevenson's classic with a top-drawer cast of 1930s MGM stalwarts, nice location filming at Catalina Island, and a memorable performance by big, boozy Wallace Beery as Long John Silver. Beery captures the blend of rascally charm, manipulativeness, and underlying danger that defines fiction's most infamous one-legged pirate. Jackie Cooper (frequently paired on screen with Beery) is pretty darn awful as young Jim Hawkins; as he's the film's protagonist, Cooper is its weakest link. The pirates are all portrayed as a scruffy, dirty, malevolent lot. Warner's DVD of Treasure Island sports a clean black-and-white restoration.
Three skull & crossbones. Worthy addition to the collector's library, although better Treasure Island versions would follow.
Captain Blood (1935) This is where the golden age of movie piracy really begins. By casting a young, relatively unknown Tasmanian hell-raiser into the lead role in a major production, Warner Brothers gambled—and won. Errol Flynn became an overnight superstar, and it's still easy to see why. No other leading man ever made perfection seem like such an effortless, natural thing. Even here, before he's got his acting chops all the way down, Flynn owns the screen. Based on the best-selling 1922 novel by Rafael Sabatini, Captain Blood is the saga of a physician who's wrongly convicted of treason during the Monmouth Rebellion of 1685 and shipped out to Jamaica in chains, only to emerge eventually as the craftiest, most daring pirate on the Spanish Main.
Erich Wolfgang Korngold's musical score is so rousing it's still performed by symphony orchestras. Here it backs up thrilling ship battles, one of movie history's best swordfights (Flynn vs. Basil Rathbone), and the first of many pairings of the star with the glowingly beautiful Olivia de Havilland. Warner's DVD of Captain Blood is the best this classic has looked in ages.
Four skull & crossbones. Essential viewing.
The Sea Hawk (1940) Five years on, with a string of box-office successes under his belt and unchallenged status as the king of the swashbucklers, Errol Flynn made this adventure masterpiece at the peak of his prowess and fame. The title derives from another Sabatini novel, but that's all the movie has in common with the source material. Flynn plays an Elizabethan sea rogue in the Francis Drake/John Hawkins/Richard Grenville mold. To the queen, he's an important captain of the crown; to his Spanish victims, he's a pirate, plain and simple.
Action and romance abound, served up with sumptuous production values and another stirring Korngold score that has entered the orchestral canon. There's also another excitingly choreographed swordfight (this one with villainous Henry Daniell). Flora Robson, one of the best movie Queen Elizabeths, delivers a stirring speech at the finale, aimed at 1940 British audiences facing the threat of Nazi Germany. Warner's DVD of The Sea Hawk offers pristine clarity. Midway through, it preserves the original tint-change as reels switch, and the image goes from silver to sepia tones for the tropics sequence.
Four skull & crossbones. A must-have for the collector's library.
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The Black Swan (1942) Yet another ostensible Sabatini adaptation, and the sound-film era's first great Technicolor pirate swashbuckler, The Black Swan stars rakish Tyrone Power, 20th Century Fox's answer to Warner Brothers' Flynn, in a rollicking salty-dog tale set on the Spanish Main. Maureen O'Hara smolders and storms in trademark fiery fashion, though you miss her usual red hair (she's brunette here), especially in such a crowning early example of splashy, colorful cinema. Laird Cregar is a standout in the key supporting role of Sir Henry Morgan.
Some of Power's ill-conceived and flamboyant costumes are downright ridiculous, and villain George Sanders' blatantly phony red beard looks like a joke, but those are things you let slide in an old movie that so thoroughly entertains overall. The swordplay is furious and frequent, the overall spirit is grog-soaked and rowdy, and the rough-and-tumble courtship between Power and O'Hara overflows with innuendo. The Oscar-winning color cinematography is vivid, gaudy, and beautifully captured on Fox's DVD.
Three and a half skull & crossbones. Certainly collector-worthy.
Captain Kidd (1945) The idea of Charles "Captain Bligh" Laughton taking on the role of history's most misunderstood "pirate" sounds intriguing. Too bad the movie's a guaranteed cure for insomnia. Kidd's just another generic movie pirate here. Several DVD editions of this public-domain title are floating around, and all are of inferior quality. You can pick it up ultracheap, but the substandard picture image and boring story combine to make this a one-time watcher at any price.
One skull & crossbone. Strictly a shelf-space occupier.
Treasure Island (1950) Walt Disney's first feature-length live-action foray is an enduring pirate-movie classic and the best overall version of Robert Louis Stevenson's oft-filmed novel. Every year on International Talk Like a Pirate Day (19 September), most people you run into going "Arrrr!" and "Shiver me timbers, matey!" might not realize they're specifically referencing the voice of Robert Newton, as heard here in one of the most, if not the most, archetypal pirate portrayals ever committed to celluloid. Newton is the definitive Long John Silver, and what's interesting in revisiting this film is how nuanced his characterization is, rather than the cartoonish clich e that years of "Arrr!" imitators have led you to expect. Bobby Driscoll also is cinema's best Jim Hawkins, American though he may sound. The DVD of this Treasure Island looks excellent; the image is noticeably sharper than on earlier home-viewing incarnations, and the colors are rich.
Four skull & crossbones. A must for the collector.
The Fortunes of Captain Blood (1950), Captain Pirate (1952) The prolific Rafael Sabatini followed up his Captain Blood novel with a couple of short story collections, Captain Blood Returns (1931) and The Fortunes of Captain Blood (1936). A hit movie plus plenty of literary source material made the character's screen reappearance eventually inevitable. Louis Hayward takes on the role with breezy style and convincing action ability. Largely forgotten today, Hayward was a fine swashbuckler in some pre-World War II movie gems. During the war he served in the U.S. Marine Corps as captain of a photographic unit, shooting footage of the brutal Battle of Tarawa. The frontline horrors he witnessed had their effect on him, and like so many other movie-star veterans, Hayward had a seasoned, slightly world-weary appearance in his postwar work that seemed due to more than just the fact he'd aged a few years. Both of his early '50s Captain Blood pictures, entertaining and well made Saturday-morning B-movie fare, are available in this two-disc set from Sony. The first is in black and white, the second in color, and both feature the ravishing '50s screen queen Patricia Medina.
Two and a half skull & crossbones each. Fun old-school adventure in a reasonably priced set; recommended for the collector. Watch a Clip 
The Crimson Pirate (1952) Burt Lancaster outgrins Flynn in this jokey, perennial favorite. There's plenty of jumping, flipping, and sundry extreme gymnastics from Lancaster and costar (and former acrobat partner) Nick Cravat. In one elaborate action set piece after another, they perform some seriously impressive gravity-defying bits, real proto-Jackie Chan stuff. But The Crimson Pirate is ultimately more of a loving spoof than anything; we're told it's the 18th-century Caribbean, but specific nationalities and the historical backdrop are amorphous and vague. Beneath all the Saturday matinee sense of fun there hides a sly political allegory. Set in its own quasi-historical universe, The Crimson Pirate may have been the first major pirate movie that was more about tweaking pirate-movie conventions than about pirates. (Nearly all would become this way.) The picture quality on Warner's DVD version is so crisp and brightly hued that the movie looks like new.
Three skull & crossbones. Overrated but fun nonetheless; probably worth a purchase for the serious collector. Watch a Clip 
Against All Flags (1952) Years of notorious and unrepentant debauchery had begun to take their toll on Errol Flynn by the early 1950s, but here, even no longer at his best, he's still better than just about anybody else. The livin'-large lush was making movies mainly just to stay ahead of his creditors at this point, but every now and then he'd rise to the occasion and the old swashbuckling magic would return. In Against All Flags, Flynn genuinely seems to be enjoying himself, a cocky, confident alpha dog who knows how to carry a picture with aplomb (provided he's able to show up on set). Here he plays a Royal Navy captain who goes undercover to smash up the pirates' lair on Madagascar. He crosses swords with Anthony Quinn and falls in love with lady pirate Maureen O'Hara-and the chemistry between the pair is combustible.
If The Crimson Pirate has somewhat of an inflated reputation among critics, Against All Flags, the best pirate movie of the '50s, is underrated and deserving of rediscovery. It's available on DVD as part of Universal's "Pirates of the Golden Age" two-disc, four-movie set. It alone is worth the purchase price, and the picture quality is excellent.
Three and a half skull & crossbones. A collection essential.
Yankee Buccaneer (1952) At one point late in the Against All Flags shoot, Flynn broke his ankle during an action scene and production had to be suspended for several weeks. Universal made the most of the downtime by using the same sets to film Yankee Buccaneer, noteworthy to U.S. Navy buffs as the movie on this list in which the grand old U.S.N. takes center stage. Jeff Chandler and Scott Brady star as Captain David Porter and a young, impetuous Lieutenant David Farragut, respectively. Their friction-fueled pairing gets the job done with the same script-formula dynamics found in countless antagonistic cop-buddy movies.
Set in the early 19th century, Yankee Buccaneer offers a Hollywoodized take on the pirate-hunting the Navy engaged in during that period. A Navy ship is tricked out in pirate-ship disguise, and the Bluejackets masquerade as pirates in order to catch the real ones. Pure hokum, indeed, but it's enjoyable to see real-life Navy figures portrayed. Since it comes as part of the same "Pirates of the Golden Age" DVD set as the must-have Against All Flags, Yankee Buccaneer is something the collector is going to own by default.
Two and a half skull & crossbones. Worth its salt as the secondary entry in a double feature.
The Master of Ballantrae (1953) Errol Flynn's final pirate picture (he would make two more swashbucklers, but not involving pirates) is a globe-trotting escapade based on the (even more globe-trotting) novel by Robert Louis Stevenson. Flynn plays the Scotsman of the title, a roguish, temperamental, self-described "ill man to cross." On the outs after the Battle of Culloden, he ends up in pirate waters, conspiring to hijack a treasure horde and return to Scotland to reclaim what he's lost. The film is fast moving and action packed, ranging from colorful Scottish locations to a bright-blue Mediterranean standing in for the Caribbean. Warner's DVD captures the image in all its vibrant glory. The pirate-minded collector will want to own it, and general-interest adventure fans will want to see it at least once.
Three and a half skull & crossbones. Highly recommended. Watch a Clip 
Long John Silver (1954) Robert Newton reprises his signature role in this Australian-made unofficial sequel to Disney's 1950 version of Treasure Island. Helmed by the same director as the Disney film (the prolific journeyman Byron Haskin), Long John Silver serves up a convoluted tale of scheming, trickery, and double-cross, and even offers a love interest (Connie Gilchrist) for the reluctant Silver. Here, even more than in its predecessor film, one can see what a direct influence the Silver character is on Captain Jack Sparrow in Pirates of the Caribbean; both stumble and swagger their way through life on a constant stream of rum-tinged pirate patter, perpetually underestimated, manipulating and outfoxing government officials and rival pirates alike.
There are several DVD editions of Long John Silver, also sometimes billed as Return to Treasure Island or Long John Silver's Return to Treasure Island. The only one remotely worth a purchase is VCI's, which has restored the film to its colorful, widescreen CinemaScope image. It's still a pretty rough picture.
Two and a half skull & crossbones. Not a library essential, but fun for Newton fans.
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Pirates of Tortuga (1961), With the post-Pirates of the Caribbean resurgence of interest in swashbuckling cinema, studios dipped into their dusty vaults for hitherto forgotten obscurities to release in hopes of cashing in on the New Buccaneer Wave. Pirates of Tortuga—what a promising title! What evocative and exciting opening credits! What a talky drag. What a letdown. This movie looks sumptuous and sharp on DVD, but it's all dressed up with nowhere to go. For long stretches, it seems like nothing happens..
One skull & crossbone. A snore; worthy of purchase strictly for genre completists only.
The Pirates of Blood River (1962), The Devil-Ship Pirates (1964) From the 1950s to the 1970s, England's legendary Hammer studio reinvented the horror film in bright, garish hues. But Hammer dabbled in a lot more than just horror, as these two colorful outings demonstrate. Christopher Lee, Hammer's biggest star and arguably the ultimate screen Dracula, makes for a mean pirate.
In The Pirates of Blood River, he's the eyepatched captain of a crew of buccaneers besieging a Huguenot settlement. In The Devil-Ship Pirates, he leads a cutthroat band of Spanish pirates turned privateers turned pirates again. Suffering ship damage after the defeat of the Spanish Armada, the buccaneers put in along the marshy English coast for repairs. They convince the nearby villagers, isolated from any news of the outside world, that the Armada actually won, and that Spain has conquered England. Can they maintain the ruse long enough to patch up and set sail? These movies come packaged with two other (non-pirate) Hammer films in Sony's "Icons of Adventure" two-disc set. The image is just a bit soft at times, but the colors jump out at you, Hammer-style.
Three skull & crossbones each. Unique stories, ample action, and the menacing presence of Lee make this pair collection-viable. Watch a Clip 
A High Wind in Jamaica (1965) This offbeat antiadventure is very much a product of the turbulent 1960s Zeitgeist. Gone are ship battles and swordfights, and in their place are moral ambivalence, grittiness, and the theme of the older generation trying unsuccessfully to shield the younger generation from life's dark side, which naturally fascinates the younger generation. Victorian parents ship their children from Jamaica back to England so that they may experience a prim, proper upbringing, but they are waylaid en route and end up on a pirate vessel headed by Anthony Quinn and James Coburn. It's the tail end of the age of piracy, and these sea-thugs are the devolved last of the breed. Soon it's "The Ransom of Red Chief" on the high seas, as the precocious youngsters impart anarchy, superstition, and general disruption of routine among the big, bad pirates.
The leader of the kids is played by Deborah Watson in one of the most memorable child-actor performances ever (she only made a couple of other movies, but a career was hers if she'd wanted it). The relationship between Quinn and the girl occasionally teeters on the very brink of creepiness, and the downer ending seems forced and illogical. Fox's DVD of A High Wind in Jamaica features both cropped and widescreen versions; flip the disc to side B and watch the movie widescreen. The restoration is less than pristine, but at least you get the entire seascape this way.
Two and a half skull & crossbones. Rent before buying; not for everybody.
Swashbuckler (1976) You'd think the puffy-shirt, big-hair 1970s would have welcomed a pirate-movie revival with open arms, but Swashbuckler landed with a thud when it hit theaters in the summer of '76. It's hard to know what to make of this infamous flop. It's not as irredeemably awful as reputed but does suffer from a certain confused tone. Coming fresh off his shark-obsessed-skipper stint in the blockbuster Jaws, Robert Shaw makes for a boisterous pirate—Red Ned Lynch. He had starred in the 1950s British TV series The Buccaneers, so Swashbuckler must have felt to him like a homecoming of sorts. James Earl Jones—young, fit, and without a touch of gray—is initially unrecognizable as Lynch's brawling first mate.
Worthwhile swordfights and action sequences abound, as does a '70s-era increase in the level of explicit sensuality. Ultimately, it's as if the movie's progressive elements are at odds with its forced efforts to be just a happy-go-lucky matinee lark like its forebears. The pirate ship, a replica of Sir Francis Drake's The Golden Hinde that just happened to be available, looks anachronistic in an 18th-century setting. The DVD of Swashbuckler presents a nice anamorphic widescreen image.
Two skull & crossbones. Rent before buying.
Nate and Hayes (1983) Raiders of the Lost Ark hit the movie world like a B-12 shot in 1981. The thrill-ride escapades of Indiana Jones set a new standard; hereafter, the pace of incident in action flicks accelerated exponentially. Nate and Hayes opens with a Raiders-esque jungle-cliffhanger bang, and the e lan continues throughout the picture.
Tommy Lee Jones brings just the right all-American gentleman-roughneck quality to his portrayal of real-life 19th-century South Seas rapscallion William Henry "Bully" Hayes, aka "the last of the buccaneers." Going from Caddyshack to pirate attack, Michael O'Keefe is along for the ride as a young missionary who seeks help in rescuing his kidnapped fianc e e and ends up learning the fine points of roguery from Hayes. The lush tropical locales look inviting in widescreen, but the film stock has that pallid, washed-out look endemic to so many movies of the '70s and early '80s. It's no fault of Paramount's DVD, which is quite adequate.
Three skull & crossbones. A little-known pirate movie worthy of finding a wider audience.
Cutthroat Island (1995) History's pirates of the female persuasion finally got their due with this hyperactive romp. As a bold piratess, Geena Davis manages to convey both radiant natural beauty and a convincing toughness; she throws a mean punch and kicks where it counts with conviction. Matthew Modine often gets a bum rap for his performance as her sly paramour; he's perfectly so-so, and the spotlight's not on him anyway. This, the ultimate woman-pirate adventure flick, has great location photography, a rousing score, action galore, and a hot-blooded heroine - in all, quite an entertaining package.
Cutthroat Island fizzled famously in its initial theatrical release, but it has gained an ardent cult following through the ensuing years on videocassette and DVD. With its unapologetically kick-butt leading lady and pirate chic, the movie just came out about a decade too early. The DVD of Cutthroat Island sports an adequate widescreen presentation, but it's non-anamorphic, so if you've got a big flatscreen you'll have to put up with a smaller image and broad black borders for the sharpest picture.
Three skull & crossbones. Deserves a more fully loaded DVD release, but current edition recommended for the collector nonetheless.
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Pirates of the Caribbean (2003, 2006, 2007) No one, not even the filmmakers themselves, could have predicted that a movie inspired by a Disneyland theme-park ride would turn into the pop-culture phenomenon of 2003. Pirates of the Caribbean: The Curse of the Black Pearl took a moribund genre, added just the right level of supernatural elements, and came up with an irresistibly fun film-going experience.
Much is made of Johnny Depp's bizarre, slightly subversive performance as Captain Jack Sparrow; Depp, obviously having a blast, took the part and ran off in strange directions with it. The character as written clearly was not intended to come off as Depp played him. But the star made pirates hip again and spawned more water-cooler impersonations than any screen scalawag since Robert Newton. The rest of the cast is likable as well, and the plot is just complex enough without being complicated to keep the ghostly skullduggery rollicking along. Hans Zimmer's lusty, swaggering score is the perfect accompaniment to the onscreen action.
The film's monumental box-office bonanza made sequels a given. Here, the genius instincts of the filmmakers went awry, for both follow-up installments—Pirates of the Caribbean: Dead Man's Chest (2006) and Pirates of the Caribbean: At World's End (2007)—took all that was magical in the first outing and crushed the life out of it. The first movie had judiciously used the supernatural to spice up a classic sea adventure (who could resist a deck battle with skeleton pirates by the light of the moon?). But in the sequels, the supernatural elements become more central, more amplified, and more numbingly over the top. The eye-popping special effects are impressive, but the humor becomes more forced, the plot becomes increasingly convoluted to the point of absurdity, and the characters' story arcs make less and less sense with each successive chapter in the saga. Disney should have opted for stand-alone adventures rather than try to craft a seagoing Star Wars trilogy.
All three Pirates of the Caribbean movies look stunning on disc (available in both standard and Blu-Ray formats) and come either as one-disc offerings, in two-disc special editions, or in boxed-set packaging.
Four skull & crossbones. The Curse of the Black Pearl Essential to the collector; a latter-day pirate classic, well worth revisiting time and again.
Two and a half skull & crossbones - Dead Man's Chest and Two skull & crossbones - At World's End Strictly optional and somewhat depressing for the missed opportunities they represent.
Blackbeard: Terror at Sea (2006) The most notorious pirate in history—Edward Teach, aka Blackbeard—has a spotty track record onscreen. Robert Newton turned him into a hammy variation of Long John Silver in Blackbeard. Roly-poly Peter Ustinov played him for laughs in the goofy Disney comedy Blackbeard's Ghost. Angus McFayden also portrayed him in a rather generic Hallmark TV production. But to date, only one screen incarnation has managed to convey the sheer dangerousness of the man. In Blackbeard: Terror at Sea, James Purefoy is a revelation as the title character. A rangy, threatening presence with a Clint Eastwood-like killer's glint in his eyes, Purefoy convinces as the cool, calculating manipulator who artfully exploits fear as a military tactic. Here is a violent, remorseless Blackbeard, simultaneously charismatic and scary.
The story authentically charts his meteoric rise and inevitable demise. Don't let the production's pedigree, a National Geographic made-for-TV offering, fool you; Blackbeard: Terror at Sea is not a documentary. It's a dramatic film, adhering to the historical record but played out with actors, well-staged action, and production values above and beyond what one would expect. It proves that a pirate movie can aspire to historical accuracy and still be exciting and entertaining.
Three and a half skull & crossbones. A collection essential. Watch a Clip