Peel and core the pineapple. Cut the pineapple into small cubes. Gently squeeze out excess juice through cheesecloth or a sieve.
In a large bowl, combine the cream cheese and shredded cheddar. Add chopped pineapple, garlic powder, and crispy bacon. Mix until smooth.
Form the "pineapple". Place the mixture on plastic wrap. Form an oval shape, tapering toward the top - like a real pineapple. Wrap in plastic wrap and refrigerate for at least 2 hours (preferably overnight).
Remove the cheese ball from the refrigerator, and remove the plastic wrap. Place the ball on a serving board. Arrange pretzels to resemble pineapple skin. Place the cut top of the real pineapple as the top.
Surround with crackers, fresh fruit, herbs, or flowers.