One of the frustrating things about Lego was the choices! We'd get to the Lego aisle and be instantly overwhelmed, wanting it all and coming away with one, but knowing all the while that whatever we came away with wouldn't disappoint, even if it was your standard Renegade's Raft or Battle Cove (both of which I know we had). Every little piece added to the Legoland mythos we were slowly building up in the bedroom. The Lego Pirates were always my favorite Lego system because they had the coolest boats and I was really into boats. Introduced in 1989, the Lego Black Seas Baracuda (pictured) had to be one of the classiest Lego products ever assembled, with its striking red-striped sails and stern-side cabin (complete with little windows), raft, real-working pulley and anchor system, plank (as in, "walk the plank!"), and two canon ports, it really just doesn't get any more cool from Lego (and that's saying a lot).
That was of course until the even more impressive Skull's Eye Schooner came along in 1993. On this one they really outdid themselves, decking it out with all the above (minus extensive stern-side cabin although it's still there), but adding taller masts, black-striped sails, and four canon ports. They even threw in a shark for good measure. So if you were lucky enough to get your hands on the best of the Legoland universe, it was still sure to be the choice of "I want both."
Then there was the more battle-rattled Red Beard Runner, which featured some more movable parts and torn up sails for combat action and functioned as the the pirate's response to the Armada Flagship. For those who don't know, the Lego Pirates system included a few spinoffs with its Imperial Armada and Islanders collections designed to give the pirates some foes to contend with and ultimately some more sets for you to buy to complete the saga. The Imperial Armada were supposed to be the "good guys," but as any swashbuckler will persuade you, the pirates were always the real good guys with the heart for adventure while the Armada was just "the Man" trying spoil the fun. That "man" (so to speak) was called Commander Broadside, the archenemy of the fierce Captain Red Beard, or so we are told. This was the equivalent of Treasure Island on my 8yo me's imagination.
Many of the Imperial Armada sets had something to do with brigs and jails for the pirates, but they also had their own fleet of ships which weren't as impressive as the pirates of course, like the Armada Flagship (also called the Royal Warship), which only had one main mast and stern sail, one canon, and movable masts for combat, so of course you just had to have both to get any high-seas adventure going. Despite this, just the contrast of the blue-striped sails and feather-hatted, stuffed-shirted soldiers clashing with the patch-eyed reds made this also a must-have, and it's actually not as small as it looks. It was joined by the more striking Imperial Flagship, which had two canon ports and was obviously designed more to go ship-to-ship with the pirates. 2010 apparently also saw the release of an even more impressive Imperial Flagship to rival its pirate archenemy, showing just how much progress they made the first time around. You can't beat the pirates, but you can certainly try!