In a microwave-safe bowl, combine chocolate chips and olive oil. Microwave on high for 20 seconds, stir, and continue to microwave at 10-second intervals until melted.

In a blender, purée tofu until creamy, scraping sides as needed. Add vanilla and purée until smooth. Add melted chocolate and purée until well blended, scraping sides as needed.

Spoon into 10 custard cups and chill, covered, for 4 hours or overnight.

In a small saucepan, combine the granulated sugar and water and cook, stirring, over medium-high heat until sugar dissolves. Bring to a simmer, remove from heat and transfer to a small bowl. Add the cranberries to the bowl and toss to coat completely. Cover and chill for 4 hours.

Drain cranberries in a colander. Place the raw sugar in a shallow dish. Roll cranberries in the raw sugar. Spread sugared cranberries in a single layer on a baking sheet and let stand at room temperature for 1 hour, or until dry.

Serve pudding topped with a dollop of whipped topping and sugared cranberries.