How do you cut/process a whole pineapple?

First, you have to peel the pineapple.

• Cut off the top and bottom of the pineapple and set it upright on your cutting board
• Using a sharp knife shave the skin off from top to bottom, following the contour of the fruit

You then have two ways to cut it into either rings or chunks:

Pineapple Rings

Next, you lay it sideways and cut it into slices as thick as you wish.

You then use a paring knife to cut out the corky centers of each slice. You now have a pineapple ring.

Pineapple Chunks

Next, cut it lengthwise down the center. Cut out the exposed corky center. This can be done with a V-shaped cut. You can then break down the fruit into chunks as desired.

Here is a step-by-step guide with photos: http://howtocutapineapple.com/

Here is a step-by-step guide on video: http://www.youtube.com/watch?v=AJJ-iQkbRNE

I never cut rings -- I always cut pineapple so it's more like a pickle spear. (I find it easier to grill that way)

• trim the bottom of the pineapple, so it sits flat on the cutting board.
• (don't trim the top, it's a useful handle)
• Hold the top, and take a sharp knife, and start at the top, slicing down along the outside edge ... you start going out, then down, then back in, to follow the shape of the pineapple. Depending on what you're going to be doing with it affects how deep you need to cut. (I've never had a problem with the occassional little brown circle; if you want to cut those off, feel free, though).
• cut off the top of the pineapple
• set it back upright again, and cut it down the middle, then rotate 90 degrees and again, so you have 4 quarters.
• slice out the center of each of the quarters ... you should see a slightly lighter bit ... that's the core, and it's kinda tough, so you want to take it out.

• slice the quarters into sticks, then chunks if you want.

• munch on the cores you removed when no one's looking. (it's not all core, so I kinda nibble on the edges)

All the other answers say "Step 1 - peel the pineapple." I don't do that. Instead, I make what our family calls "boats". In addition to being a pretty presentation, it's a way less messy way to handle the fruit; you're not wrestling with a peeled and juicy pineapple and you lose way less juice. We cut pineapple this way even when we intend to toss the chunks into fruit salad or something.

• Cut the pineapple lengthwise in half. Do not trim or cut anything else off yet. The leaves, bottom, all the skin are still on and you actually cut the top leaves in half too.
• Cut each half lengthwise in half. Now you have four wedges, each a quarter of a pineapple, each with a tuft of leaves at the top.
• Lay a wedge skin-down on the board. Make a vertical cut partway through (just to the skin) close to the bottom, separating the bottom you might otherwise have trimmed off from the main body of the fruit, but don't cut through the outer skin
• Make a similar vertical cut by the top, again not cutting through the outer skin
• Holding your knife parallel to the cutting board, get under the corky triangle at the top of your wedge and cut it away. Because the main part of the pineapple is still attached to the skin, this is easy to do
• Make a lengthwise cut (from the leaves to the bottom) straight down (from where the core was towards the skin) but as before stop when you reach the skin. At this point your wedge has the core removed and has two spears that are only connected on one side to the outer skin.
• If you want spears, slice underneath them to free them from the skin.
• Assuming you want chunks, cut vertically repeatedly (again stopping just before the skin) to make the spears into smaller pieces, then slice underneath them to free them from the skin.
• You can now turn the boat over and drop the chunks and juice into whatever you want the pineapple for, or simply put the boat on a plate and serve it to people. Optionally, give them toothpicks to spear individual chunks with.
• If you really want to show off, push every other slice to the left or the right so that the slices are staggered and easier to pick up.

There are some pictures at http://pinecreekstyle.blogspot.ca/2012/05/pineapple-boat.html though that person does the steps in a slightly different order than I do and takes the leaves off.

if you're not going to use a pineapple corer (which I don't), grab a sushi or a long sharp knife, and:

• deskin the pineapple like you would cutting a donair
• cut a square around the core
• push the core out
• Now you have a hollow cylinder
• if you want chunks the type you put on a pizza:
  • Cut the pineapple with the required thickness
  • and then just chop it like you'd chop a tomato or mango

A slightly different technique than the one in hobodave's post.

a picture speaks a thousand words: http://www.youtube.com/watch?v=GViaOUTC3rY

this technique gives you a nice looking pineapple at the end, with the pieces able to be eaten like a lolly.

Pineapple Rings

Pineapple Slicer

This thing is sweet.