Add egg, milk and vanilla extract to a blender and blend for about 1 minute. Alternatively, you can add ingredients to a medium bowl and beat with an electric mixer. Pour mixture into a shallow baking dish and set aside.
Melt 1 tablespoon in a griddle or medium skillet set to medium heat.Dip both sides of bread into egg mixture. Place on griddle and cook for about 5 minutes.
While bread is cooking, sprinkle one tablespoon of brown sugar on each slice of bread. Add one pineapple ring to each slice of bread.Turn bread and cook on the other side for about 5 minutes or until well-browned and brown sugar is melted. Serve immediately.