Heat oven to 400°F. Spray 9-inch tart pan with removable bottom with nonstick cooking spray. In small bowl, combine cookie crumbs and 2 tablespoons of the melted spreadable fruit; mix well. Spray hands with nonstick cooking spray. Press mixture in bottom of tart pan.
Bake at 400°F. for 5 minutes. Remove from oven; spread remaining 3 tablespoons spreadable fruit over crust. Freeze 5 to 8 minutes or until cool.
While crust is cooling, in small microwave-safe cup combine chocolate chips and 1/4 teaspoon of the oil. Microwave on HIGH for 40 to 60 seconds or until melted. In another microwave-safe cup, combine vanilla milk chips and remaining 1/4 teaspoon oil. Microwave on HIGH for 30 to 40 seconds or until melted.
Arrange raspberries over cooled crust; drizzle with melted chocolate chips and vanilla milk chips. Serve immediately or refrigerate until serving time. To serve, remove outer ring from tart pan; do not remove bottom of pan.