For the Oven-Grilled Pineapple- Preheat your oven to 400 degrees Fahrenheit. Place an oven-safe rack (or grill pan) on a large enough baking tray, spray with cooking spray, and place it in the oven. Cut the pineapple rings in half. Remove the hot tray from the oven and place the pineapple slices on top about 2” apart. Bake for 9 minutes. Remove the pan from the oven and use tongs to turn the slices over. Bake for another 9 minutes. Let cool completely.
Place a pineapple slice into 6 sundae cups.
Scoop ⅓ cup of Halo Top into each of the sundae cups.
Then, scoop ¼ cup of frozen whipped topping, and top with another ⅓ cup of Halo Top. Freeze for 1 hour.
Garnish with a maraschino cherry. Feel free to add an extra helping of whipped cream, a sprinkle of shredded coconut, and a wedge of fresh pineapple. Enjoy!