One thing entertainment is known for is its waves, with one show, movie or song after another coming out that seems to chase the latest trend, fad or meme. From autotune-centric pop songs, to Hollywood deciding the world needed not one but two mall-cop movies, we’ve seen it all. But film, literature, and the video game world have shown there are a few things that never go out of style.

Some genres are truly timeless. We all can’t help but love pirates, and aside from Assasin’s Creed: Black Flag (which is AWESOME), there hasn’t been anyone new stepping into the swashbuckling soles vacated by Johnny Depp and the Jerry Bruckheimer’s Pirates of the Caribbean crew, let alone a cable TV series based upon the life of a motley crew of freebooters.

Enter Starz’ new show Black Sails — premiering Saturday Jan. 25 — which takes place just before the era Robert Louis Stephenson’s book Treasure Island made legendary. If early indications hold up, it is just the market correction that will jumpstart a new wave of privateer-focused entertainment. Here are five important questions that Black Sails will have to answer:

Does anyone remember Treasure Island?
The thing about prequels is that they give us characters we are hyper familiar with before we met them. It gives us a chance to see how they came to be the character we know, and in the best cases adds depth to an already established character. While Stephenson’s Treasure Island is without a doubt a literary classic, it doesn’t strike me as one that’s seen enough recent adaptations to be make viewers go, “Ohhhh, so THAT’S how they meet so-and-so,” or, “Wow, in light of what he’s doing in this episode it makes what I know comes later all the more poignant.” The fact that the last relevant adaptation was 1996’s Muppet Treasure Island should give you a good idea of where the story lies in pop culture’s collective memory.

Who will lead the show?
From Bryan Cranston as Breaking Bad’s Walter White, to James Gandolfini as Tony Soprano, it’s become blatantly clear that a show can go about as far as it’s best performers. Toby Stephens as Captain Flint — the man who buried the titular treasure that the characters in Treasure Island pursue — has the opportunity of a lifetime. Can he really carry this show into 5-7 seasons? Also the supporting cast’s chops will be watched closely. Who will fill the Omar/Jessie Pinkman aka unexpected scene stealer role? Only time will tell.

Will the Michael Bay explosion factor translate to the small screen?
The much maligned yet commercially successful director will be trying his hand at the small screen and one has to wonder what he will do given the challenge of pacing a series. He’s known for his mile-a-minute, blow-it-all-up style of summer blockbuster grandeur. Something that doesn’t traditionally lend itself well to keeping its audience interested over the course of months as opposed to grabbing them and not letting go for 2 hours. As TV quickly becomes a place for both actors and directors to display their full range of talents, it will be interesting to see if Bay becomes the next show runner to keep us tuning in week after week.

Will it be better than Crossbones?
Remember when we talked about waves, market corrections and saturation? Well get ready for TWO, count em’ TWO pirate shows soon. NBC’s Crossbones will feature the legendary John Malkovich as the pirate other pirates feared, Blackbeard. Add that to the fact that the mind behind BBC’s Luther is involved and you can see the lines being drawn in the sand. While Black Sails is attempting a dark and real take on a fictional pirate, Crossbones’ attempt is based upon an actual historical figure. With the cable vs network TV limitations/freedoms one would think that some storytelling devices available to Sails may give it an edge — it certainly will be able to show more gore, lesbian sex and dirty talk (Like the premiere episodes best line given by Hannah New as the pirate island’s shot caller, Eleanor Guthrie, “Earners make my pussy wet”). Plus, NBC has already blinked, bumping Crossbones to the Fall of 2014 in favor of more Hannibal.

Will it be a success?
Starz seems to think the answer is a resounding ‘yes,’ having made a massive bet on an elaborate set that will take many seasons to truly amortize its cost. But CEO Chris Albrecht has already doubled down by ordering a second season before Black Sails’ Jan. 25 debut. This is a big risk, but the network is smart to reassure potential veiwers made uneasy by the channels penchant for cancelling shows after two seasons as it did with the celebrated show Boss and the Mad Men-meets-Sopranos show Magic City. If it becomes a hit it could make good on Starz big push on quality originals and open the doors for further mining of classic literature. I mean, with Sails, Sherlock and Sleepy Hollow, maybe I’ll finally get the 80-episode Around the World in 80 days show I’ve been dying for since I was a kid.

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Pirates, knights, cops, robbers and cowboys are always running amok on FilmOn Classics:

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