Cut off the green top (crown) of the pineapple. Peel the pulp from the skin and tough core, and chop the pineapple into small pieces. Squeeze the pineapple to release excess juice - allowing to drain a few minutes.
Place the softened cream cheese in a bowl. Mix it with the grated cheddar.
Using your preferred method, cook the bacon until crisp, and chop into small squares.
Combine the pineapple, cream cheese and cheddar mixture, bacon, and garlic powder in a bowl. Mix until well blended.
Place the mixture on a large piece of plastic wrap, shape into an oval, tapering towards the top. Tighten the wrap on the open ends and leave the cheese ball in the refrigerator for 4 hours to overnight. (The longer, the better!)
Place the pineapple cheese ball on a board, insert the top (crown) of a real pineapple into the more narrow part (top) of the cheese ball. Cover the appetizer with pretzels to mimic the outer texture on a pineapple, pressing lightly.
Serve the appetizer on a board with crackers or chips.