Slice off the top. Place the pineapple on its side on a large cutting board. Secure the pineapple with one hand and using a large, sturdy chef's knife to slice off the top (approximately 1/2-inch from where the green crown and pineapple flesh meet).
Slice off the bottom. Rotate the pineapple and trim approximately 1/2-inch from the bottom of the pineapple.
Slice away the outer peel. Place the pineapple upright on the cutting board. Holding the pineapple in place with one hand, use the knife to carefully cut away the outer peel, slicing down from top to bottom. Careful not to cut away too much of the flesh as the outer edge of the pineapple has the sweetest flesh.
Remove any brown "eyes" left in the pineapple. Using the same knife or a small paring knife to carefully remove any of the brown "eyes" remaining in the pineapple.
If making pineapple rings, place the pineapple back on its side and cut the rings into desired thickness. Use a small round cookie cutter, biscuit cutter, or paring knife to carve out the middle core.
To chop the cleaned pineapple into small chunks, cut the pineapple in half vertically through its center. Cut each half in half again (now you'll have 4 equal-sized pineapple pieces).
Cutaway the core. Working one at a time, place the pineapple wedge upright on the cutting board and cut the thick fibrous core from the center (the core is usually pale, and lighter in color when compared to the pineapple flesh).
Chop into chunks. Slice each wedge in half lengthwise again and chop into slices, larger chunks, or small bite-size-pieces.