Special equipment: wooden skewers, soaked in water for at least 30 minutes
Preheat an outdoor grill.
Peel and cut the bananas into 1/2-inch thick slices. Trim the top off the pound cake and cut the rest into the same size squares as the banana chunks. Cut the top and bottom off the pineapple and remove the rind from around the sides. Cut the pineapple in half and then into quarters. Trim the core and cut each piece again lengthwise. Cut the strips into 1/2-inch thick pieces. On a wooden skewer, alternate pieces of banana, pound cake, and pineapple until the skewer is full, leaving about 2 inches for a handle. You should have 8 to 10 skewers. Finish with a cherry. Brush with melted butter and grill for 1 to 2 minutes on each side. (Alternatively, you can broil the skewers for about 1 to 2 minutes per side.)
Meanwhile, heat the cream in a small pan over medium heat; do not let it boil. Add the chocolate to the warm cream. Let sit for a few minutes, then stir the mixture to melt all the chocolate. Cool for a few minutes and pour into a squeeze bottle.
Scoop ice cream into bowls and top with a skewer. Squeeze some chocolate sauce over top and serve.