Mix sugar and oleo. Add egg and vanilla. Stir in flour. Cover and refrigerate for 1 to 2 hours.
Shape dough into balls. Place 2" apart on cookie sheet. With thumb, make imprint in each cookie. Bake for 12 to 15 minutes in a preheated 350° F oven. Remove from cookie sheet and cool.
Mix filling and fill cookie center with ½ teaspoon of filling. In saucepan, melt chocolate chips and oleo. Mix in rest of ingredients and drizzle over cookies.