In the “Class of …” series, Nick Rogers takes a monthly look back at films celebrating either their 20th or 30th anniversary of initial release this year — six from 1995 and seven from 1985 (the extra from August’s double-feature column). The rules: No Oscar nominees and no films among either year’s top-10 grossers.

Time confers a certain absolution on megaton box-office bombs that their legendarily red ledgers do not.

Protective fans help morph once-unmarketable madness into cult eccentricity (The Adventures of Baron Munchausen, Hudson Hawk). Audiences simply age out of even understanding the punchlines (Gigli, Ishtar). More often than not, most folks — and cable networks — just forget these failures ever existed in the first place (The 13th Warrior, The Adventures of Pluto Nash, Final Fantasy: The Spirits Within). 

Fiscal infamy fades even further in the modern blitzkrieg of box-office news, where fortunes are now foretold months, or even years, before a film hits theaters. And the major studios’ year-round, go-big-or-go-home approach didn’t exactly exist back then. The good number of medium budgets in the mix only further magnified any big-budget follies. On four films since 2011, Warner Brothers lost up to $400 million. Over that same time, five other Warner Brothers films raked in a collective half-trillion dollars.

If you can call that risk at all, it’s not just comfortable. It’s luxurious.

This business evolution into billions-or-bust has burnished the reputation of few megaflops more than it has for 1995’s Cutthroat Island, a bomb whose detonation destroyed one prolific production company, two thriving careers and, for several years, any serious thought of dropping a doubloon on a movie about pirates. Island once held the Guinness World Record for the largest box-office loss at $88 million, but that category has been retired. What’s so special about a designation that has changed 13 times since? This year alone, Jupiter Ascending and Pan each lost that much.

To watch Island today is to see just how much of it Disney’s Pirates of the Caribbean: The Curse of the Black Pearl simply did better eight years later. A partnership between unctuous upper-crusters and treacherous pirates to pursue a treasure? A Capuchin monkey for comic relief? Somebody who looks like Orlando Bloom? An award-winning actor hamming it up as a bad guy? Destroying harbor towns around the Caribbean? A purposefully unlikely action hero? That’s a half-dozen checks. Prettier supporting players, supernatural undertones and intentional connections to the theme park ride for beloved corporate synergy are the only real changes in Black Pearl.

So … why didn’t Cutthroat Island reap the same reward? Carolco Pictures simply threw the very last of its good money after up to $115 million of bad into the definition of a vanity project. (Some might say the same about that year’s Waterworld, but at least it made some money for Universal Pictures.)

In the 10 years prior, Carolco — it of the unassailably cool opening-credits logo — produced, among others, a pair of profitable Rambo movies, Total Recall, Terminator 2: Judgment Day, Basic Instinct, Cliffhanger and Stargate. In 1995, Carolco executives bankrolled Island instead of Paul Verhoeven and Arnold Schwarzenegger’s historic epic about the Crusades, one of the most mythologized unmade films of the 1990s. (They instead let Verhoeven make Showgirls, which like Island, carried a bloated budget, bad press and stiff Razzie competition.)

Whatever brought on Carolco’s fiscal mismanagement certainly doomed them well before Island ran aground, but it nevertheless became a convenient scapegoat; only this year has the Carolco brand reemerged under new ownership, and with one of its long-time leaders, Mario Kassar, hired to help develop projects.

Hot off a hit Die Hard sequel and Cliffhanger, action director Renny Harlin saw Island as his path to becoming an artistically independent icon of spectacle a la James Cameron and anointing his newlywed Oscar-winning wife, Geena Davis, as the next great female action star. She plays Captain Morgan Adams, commander of the Morningstar who avenges her father’s death at the hands of her uncle Dawg (Tony winner Frank Langella) and pursues a bountiful treasure on the titular island.

(For all of Island’s issues, Langella fondly reflects on Dawg as one of his favorite roles, and it’s easy to see why. Dawg is the sort of scoundrel who, when confronted with a food shortage, feeds bullets to underperforming members of his crew. Langella is arguably the only one truly having fun here. He fixes his gaze of fury with fervor, shouts “I love this!” during a swordfight, acquires the best tan of his life in the process and seems fully aware that if he could survive playing Skeletor in the similarly maligned Masters of the Universe, he could, and would, surely emerge unscathed from this.)

Island was the first of Harlin and Davis’s two-pronged Hollywood honeymoon plan, alongside 1996’s The Long Kiss Goodnight. That R-rated caper is certainly more in Harlin’s wheelhouse of grisly misanthropy … or maybe New Line Cinema had spent so much at that point that they couldn’t simply cancel it in the wake of Island’s misfortune.

Harlin’s signature slow motion lets you linger on the craftsmanship behind his chaos, at the center of which he prefers to place his actors whenever possible. There are at least a half-dozen long shots in Island where it’s certainly Davis and co-star Matthew Modine scampering around; in one scene, Modine appears to be conked in the noggin by a blasted barrel. Davis achieves the believable physicality that Tom Cruise has made his stock-in-trade today. If that’s not really her faux cold-cocking foes, barreling through windows, rolling off balconies into a moving carriage and riding away from explosions during a fiery siege on Port Royal in Jamaica, Island has some of the best stunt doubles of all time.

Sadly, said carriage’s swift acceleration through clumps of horseshit in an attempt to keep moving speaks volumes to what doesn’t work in Island. Propulsion and a persuasive sense of place aren’t the problems In fact, Harlin’s juggernaut bombast wears you down into a sort of slightly stimulated submission, especially when the Morningstar does battle with Dawg’s Reaper in the final act; this is point-blank expenditure of all the ammunition at which Harlin excels, and the ensuing explosion is divine. Multitudes of extras mill about in believable bustle behind the actors. Sets above and belowground are ornate and detailed. John Debney’s majestic, exciting score is one of the decade’s best for an action film, particularly in its regal opening fanfare.

You can certainly see where, and how, all of this money was spent. But Harlin’s camera often feels like it’s simply canvassing all this costly collateral rather than conjuring any movie magic. So focused, too, was he on foisting stardom upon Davis that he forgot to let her intrinsic charisma flourish — a flaw he admittedly fixed in Goodnight, largely due to that script’s more accomplished characters. (More on that movie, and the personal and professional fallout for Harlin and Davis, to come in a 2016 “Class of …”) Where Island could be larger than life, it is merely matter of fact.

A fire sale of genital gags passes for repartee in a crudely stitched by-committee screenplay from Bruce Evans and Raynold Gideon (Oscar nominees for Stand By Me), Robert King (eventual creator of CBS’s The Good Wife) and Marc Norman (who won an Oscar in 1998 for Shakespeare in Love despite Tom Stoppard’s heavy rewrites). Basic connective tissue seems to have eroded somewhere along the line, such as how and when certain characters debark or re-board the Morningstar.

Plus, Davis is paired opposite a real limp noodle in Modine, who was — get ready — the 12th choice to play Shaw, a roguish lout and eventual love interest for Morgan.

Michael Douglas originally agreed to play Shaw on two conditions: Filming had to accommodate his busy schedule and his role would be expanded to equal Davis’s screen time. Douglas allegedly bailed after rewrites grew Davis’s role, and it’s suggested even she and Harlin wanted to back out but faced severe contractual penalties.

So began Harlin’s brutally long search for a leading man, purportedly rejected by Tom Cruise, Keanu Reeves, Liam Neeson, Jeff Bridges, Ralph Fiennes, Charlie Sheen (!), Michael Keaton, Tim Robbins, Daniel Day-Lewis and Gabriel Byrne. (One wonders, given the breadth of that list, whether Johnny Depp’s name ever seriously crossed anyone’s lips.) The PR spin on Modine, who hadn’t headlined a feature since 1992? He can actually fence!

Modine certainly doesn’t seem miserable to have been a dozen spots down the dance card, and his much-ballyhooed fencing is fine enough. But Modine’s untouched mid-’90s hair makes it seem like he wandered in from a short-lived ABC sitcom where he plays the bad boy, and there’s also a vacant abyss where Shaw’s scalawag soul should reside. One of Shaw’s go-to lies to mask his pickpocket prowess is that he’s an upstanding doctor. Instead of simply making that a fraud, why not really make him a doctor and reveal how he was laid low? It’s the sort of positive studio note a production company not simply struggling to stay afloat may have insisted upon, and it’s easy to see why so many actors passed on the part as written.

The delay in finding the right (or even any) man to play Shaw sent the budget skyward. An impatient Carolco hired crews to build sets and assigned screenwriters. Displeased when he finally saw what they’d done, Harlin ordered the sets struck and the script retooled — an acrimonious retaliation fueled by $1 million of his own money after Carolco balked at spending more on those items.

Eventually, cameras rolled on a six-month shoot. Dozens of crew members left the production after bad blood erupted between Harlin and a chief camera operator. Broken pipes at a Malta studio caused sewage to spew into a tank where actors were swimming. Original cinematographer Oliver Wood broke his ankle in an accident on set and was later replaced. The closing credits list drivers for Harlin and Davis, who presumably rode to set together; oh, to be a fly on the wall for those conversations.

Some might argue that the unruly, disorderly nature of the Island shoot count as some sort of thematically appropriate badge of honor in piratic filmmaking. The film has a certain ramshackle charm, but Harlin never quite harnesses it in the right way.

Island’s outlook didn’t improve from there. MGM, which distributed the film, was in the midst of a sale and barely marketed the movie. Carolco filed for bankruptcy a month before its release. And in its Christmas-week opening, “Island” wound up marooned in 13th place — racking up totals of only $10 million domestically and $8 million internationally. Strangely enough, were Island made today, it might have recouped its cost in foreign lands; after all, international grosses have pretty much kept the Pirates of the Caribbean franchise afloat for a fifth round in 2017.

The very existence of that fifth Pirates, for better or likely worse, continues to nudge Island closer toward the side of novel curiosity than cautionary tale; more so than Roman Polanski’s Pirates (which itself imposed a decade-long genre drought), it now feels less like a giant bomb and more like a profitable formula that wasn’t quite finished. Cutthroat Island isn’t the landlubber suggested by its reputation. But if all involved knew they were going broke, they should have gone for broke to boot.