I remember the first time I saw one of the Salvadoran prep cooks at a restaurant where I worked slice up a pineapple for us to eat as a cool snack on a particularly hot night. The pineapple was great, but the truly awesome part was the way in which she prepared it. Up until then, I was of the just hack away until it looks like I can eat it school; as a consequence, I ended up throwing a lot of edible bits into the trash along with the skin.
Her method, which I've since seen everywhere from the streets of Cartagena to the streets of Bangkok, was to remove the dark, spiny eyes with a series of shallow, diagonal, wedge-shaped cuts. It takes a bit of practice before you can do it efficiently (I'm still nowhere near as fast as she was!), but the reward is a much higher yield of pineapple (read: fewer sweet edible bits in the compost), and the ability to look badass and inspire badassery in anyone who sees you do it.
Here's how it's done.
Step1: Trim off the top
Slice off the top of the pineapple, being generous with the slice. The top of the pineapple can be pretty woody and fibrous.
Step 2: Trim off the bottom
Similarly, be generous when you slice off the bottom.
Step 3: Trim the sides
Stand the pineapple on its end, then slice off the sides, working your way around the pineapple. Here, it's better to be conservative with how much you remove. Take off just enough so that there's no dark green or pale brown skin remaining, but don't worry about taking out the eyes just yet, we'll get to them.
Step 4: Identify the pattern in the eyes
Once you have the sides removed, you should be able to identify a distinct array of straight parallel diagonal lines that connect all the eyes. You're going to be cutting them out along these lines.
Step 5: Start slicing eyes
Start by cutting your knife into the pineapple along one of these lines at an angle so that your knife slides underneath them. Don't cut too deep, and don't try to get too many at a time.
Follow that cut up by slicing along the opposite diagonal, removing the eyes in a single wedge.
Step 6: Take out rows of eyes in wedges
Keep working around the pineapple, taking out wedge-shaped rows of eyes as you go.
Eventually you end up with this: eye-free, and very high yield.
Step 7: Split lengthwise
Next, split the pineapple lengthwise into halves...
...then into quarters (or sixths if you prefer).
Step 8: Trim out the core
Like the top and the bottom, the core can be very woody, so it's best to remove it. Stand a wedge up on its end, feel the fibers to see where it starts to get tough, then slice down to remove the core.
Step 9: Slice into bite-sized pieces
Slice each wedges crosswise into bite-sized pieces (or if tacos al pastor are on the menu (and they should be!), leave those big wedges intact!).
Step 10: Serve
Arrange your slices, serve, and let the badassery commence.