Combine ice cubes, coffee, milk, and syrups in a blender or food processor. Blend until completely smooth, about 30-60 seconds. Pour into serving glasses, top with whipped cream, and drizzle with chocolate syrup and/or raspberry puree.
To make the raspberry drizzle, combine the about 1 cup of raspberries with 2-3 tablespoons of sugar in a medium saucepan over medium heat. Cook, stirring occasionally, until the berries have released most of their juices and the juice has reduced a bit, about 10 minutes. Puree the berries with in a blender or with an immersion blender. Pour the mixture through a fine mesh sieve and discard the seeds. Chill.