I’m a little shocked at how many figures in my backlog fall into the “pirates and swashbucklers” category. Doing another sweep I remembered I still had 20+ plastic pirate crew from the “Weapons & Warriors” game, 10 or so dwarves with guns and horned helmets that seemed seaworthy, and about a dozen Landsknechte (who technically would be a little early and landlocked for Age of Sail gaming but who are a) flashy, b) mostly unarmored, and c) armed with guns or Zweihanders, so they really fit in better here than Medieval fantasy or Modern/Sci-fi which are the other two categories I tend to put RPG minis into).
The plastic pirates were a challenge because there are so many and they ought to be non-uniform. What I ended up doing was limiting them to 20 and breaking them up into groups of five, each of these four groups getting a single color for their shirts and trousers. Then I chose five different colors for their bandannas and sashes, and used them on up to 1 from each group of four. Lastly I used dark brown on half and black on half for their vests and shoes. So, no two are exactly alike but I can easily form groups of various sizes (4 blue bandannas, or 5 blue shirts, or 8 blue anything, or 10 black vests, etc.). I will probably number their bases too.
I used a lazy but fast shading technique that I’ve been experimenting with a bit: a black wash (which I used to do back when I started painting, knowing no better) but with some Future Floor Finish mixed in to greatly reduce the surface tension and allow better pooling into crevasses than plain paint and water would. This basically creates an effect like black lining (which is very tedious) and adds a simple shading in one step. I’ve tried Minwax “Polyshades”for the same purpose (with has the added benefit of being a polyurethane varnish too) but it tends to make things look too dirty, like a regular black wash. The new wash mix is not perfect, especially on the orange and yellows, but pirates should be dirty so I’m OK with it. I can’t imagine getting 20 pirates done in three 1 hour painting sessions otherwise!
At some point I may add eye patches (to the ones with the sloppiest eyes) and mustaches (the figures look like they either have bushy mustaches or really heavy sneering lips). I might also go back and give half of them darker skin tones, since historically pirates could be from anywhere.
They all seem to have a pistol in one hand and a sword in the other, with what might be a knife tucked into their sash. (One detail that I like is that the swords are manifestly NOT cutlasses, which only became common in the early 19th century. In the golden age of piracy, the swords might be anything, and the short hangers they have look right).