Having written that, Fast Ships, Black Sails is a very odd collection. More science fiction and fantasy stories with sea-going (or space faring) elements grafted on than tales of pirate living (and pirate dying) than I expected, that is sure. I would suspicion that editors Ann & Jeff VanderMeer did not have a wealth of choices when they put this together, but also that their collective taste is quite broad. The only author whose name I recognized was Michael Moorcock (I've noted previously that I had never read anything by him), but some have had quite a lot of success it would seem.
Some of the stories – "Boojum", "Pirates of the Saura Sea", "The Whale Below", and “Beyond the Sea Gate of the Scholar Pirates of Sarsköe” – felt like they were conceived as novels or novellas and condensed in order to find publication. This isn't much of a complaint, but rather an observation that there seemed to be much more in the backgrounds that the authors wanted to write about, and that the pacing may have been better if they were allowed to run more than 50 pages.
Some of the stories were just horrible. Waldrop's "Avast, Abaft" steals from Gilbert & Sullivan, has no narrative flow, and (worst of all) has no fucking point. Moorcock's "Ironface" felt more like a couple of pages of notes with the veneer of prose to hide the fact that he had nothing going on. Thanks for the notes on a guy in a setting, Mike, but where was the story you were going to submit? "Pirate Solutions" has the less than savory pirates=hackers theme, but it also has odd jumps in terms of whose narrative it is and a total lack of concept for what is propelling the activity (or, if there is one, it is completely at odds with the rest of the tale). Connell's "We Sleep on a Thousand Waves Beneath the Sea" is a poorly written story that seems to fight having any sense of self until the very end, and not because the author was trying to be clever.
You want something even worse than horrible. Okay. When anyone asks me what the worst thing I’ve ever read (that wasn’t self-published), I will point to Aylett’s “Voyage of the Iguana”, an unfunny, mostly unwritten, yet terribly long excuse of a story. Just a piece of shit. I'm sure he thought it was smart, clever, and sly. It isn't. It is the equivalent of used toilet paper: it is shit on the page.
There were some stories that just weren't what I thought they'd be. Barnhill's “Elegy to Gabrielle, Patron Saint of Healers, Whores and Righteous Thieves” never comes together as a story (which I thought it would), remaining a shadow of someone retelling a tale. Howe's "Skillet and Saber" gets a little too caught up in the dread of forced sodomy, decides that a lot of the characters don't need to be developed, and the ending should try to work in a staple of the pirate mythos. Freer & Flint's "Pirates of the Saura Sea" had some good elements, but felt like they were more interested in the setting than the story. Blaschke's "The Whale Below" tried to mix technologies (airships and flintlocks) to poor effect and was overwrought with the author's need to make the crew as Spanish (or maybe Portuguese) as possible, but there was a rather decent story trying to escape those traps. Swirsky's “The Adventures of Captain Black Heart Wentworth” was much more straightforward than I expected; you give me rats as pirates, firing guns at ducklings, and I am expecting it to be much more tongue-in-cheek.
So, what really worked? Hughes' "Castor in Troubled Waters" has nothing to do with pirates and everything to do with British pub humor. I know only a little of that brand of storytelling, but this short story was witty and winning. Vaughn's "The Nymph's Child", while a little too friendly with its dragon fantasy element, is well written and engaging. Batteigger's "A Cold Day in Hell", where Ice Pirates (1984) meets...well, pirates on the ice. A good example of how to sell a setting with little notes through the story rather than trying to hammer it out in huge chunks. And, of course, Nix's “Beyond the Sea Gate of the Scholar Pirates of Sarsköe". So much of the setting is missing (the characters in this story apparently have appeared in a novella prior to this adventure, so I'm betting he felt it was as developed as it needed to be) as to make the reader curious more than frustrated.
Overall, I don't think I can recommend Fast Ships, Black Sails. But how many collections of short stories are full of must read writing? There are some good stories, and it is certainly telling how some people approach telling stories in a shorter format (and that the editors let them get away with it; Naomi Novick, I'm referring to you and your blatant abuse of the comma). For the regular reader of Sci-Fi and fantasy, most of these will be in your comfort zone. But there isn't a lot of examination of what it means to be a pirate, or the life of a pirate. And I was kind of hoping for a little of that.
▸ “Boojum” by Elizabeth Baer & Sarah Monette
▸ “Castor in Troubled Waters” by Rhys Hughes
▸ “I Begyn as I Mean to Go On” by Kage Baker
▸ “Avast, Abaft” by Howard Waldrop
▸ “Elegy to Gabrielle, Patron Saint of Healers, Whores and Righteous Thieves” by Kelly Barnhill
▸ “Skillet and Saber” by Justin Howe
▸ “The Nymphs Child” by Carrie Vaughn
▸ “68̊ 07'15"N, 31̊ 36'44"W” by Conrad Williams
▸ “Ironface” by Michael Moorcock
▸ “Pirate Solutions” by Katherine Sparrow
▸ “We Sleep on a Thousand Waves Beneath the Stars” by Brendan Connell
▸ “Voyage of the Iguana” by Steve Aylett
▸ “Pirates of the Suara Sea” by David Freer & Eric Flint
▸ “A Cold Day in Hell” by Paul Batteiger
▸ “The Adventures of Captain Black Heart Wentworth” by Rachel Swirsky
▸ “Araminta, or, The Wreck of the Amphridrake” byy Naomi Novik
▸ “The Whale Below” by Jayme Lynn Blaschke
▸ “Beyond the Sea Gate of the Scholar Pirates of Sarsköe” by Garth Nix
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