Begin by cutting up your pineapple into spears, and then place in a zip bag with brown sugar. Seal and shake to coat the pineapple in sugar, set aside until ready to grill.
Heat oil to 375 degrees, and place tortilla bowls in oil one by one, turning as needed and frying until golden brown. Immediately when the bowls are removed from the oil, sprinkle all over with cinnamon sugar, so that it will stick.
Grill pineapple on the bbq.
Serve the cinnamon sugar tortilla bowls with ice cream, grilled pineapple, and other toppings. Enjoy!