For sauce, in a small saucepan heat port to boiling; reduce heat. Boil gently, uncovered, 3 to 4 minutes or until reduced to 1/3 cup. Add 1 tablespoon sugar; cook and stir 1 minute. Add cherries; cook 2 minutes more, stirring occasionally. Remove from the heat and whisk in butter; cover to keep warm.
Meanwhile, heat oil in a 2-quart saucepan over medium heat until temperature reaches 350 degrees F. While oil heats, lightly brush edges of one wonton wrapper with some of the beaten egg. Place 1 piece of chocolate in center atop wonton wrapper. Place another wonton wrapper atop. Press edges to seal.
Cook filled wontons, one at a time, in hot oil for 1 minute or until golden brown, turning frequently to brown evenly. Remove with a slotted spoon and drain on paper towels. Adjust heat as needed to maintain oil temperature. Cool wontons slightly. Sprinkle wontons evenly with sugar.
Serve wontons with sauce and ice cream. Sprinkle ice cream with grated chocolate and serve with two spoons. Makes 2 servings.