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Make cookie dough. Cut out 1 tree and 3 baskets. Use gingerbread boy cutters to cut out a variety of family members. Bake and cool.
To make basket handle, on waxed paper use royal icing to pipe tip 14 "rope" handle; let dry. When completely dry, turn over and repeat. Let dry; set aside.
Stack and ice 3 basket pieces together with royal icing; ice top smooth. Pipe tip 14 basketweave on sides and tip 3 rope top border. Attach basket handle with royal icing.
Use tip 18 and royal icing to pipe stripe trunk and branches; add tip 352 pull-out leaves. Decorate family members with royal icing: Pipe-in tip 3 clothes (smooth with finger dipped in cornstarch). Pipe tip 2 string or tip 16 swirl hair. Cover some clothes with tip 16 stars. Outline tip 1 facial features, dots, flowers and stripes on clothes. Let dry.
In buttercream, ice 1-layer cake. Using toothpick, mark a 7 x 8 in. area on cake top and divide into 1 inch squares. Pipe-in tip 16 star checkered tablecloth.
Use royal icing to attach lollipop sticks to backs of cookies except two with jump rope. Pipe tip 233 pull-out grass bottom border.
Insert cookies into cake. Position basket on tablecloth. Attach two children jumping rope to cake side; cut shoestring licorice and attach in hands with icing.