Bet your bottom dollar that tomorrow there'll be sun.  I always love when I receive requests for cookies that I've never made before.  It's been a long time since I've seen the movie "Annie".  But I remember the main parts of the movie to make the cookies. 

I used this Ecko girl cookie cutter to create Annie, found on Ebay.  I cut off her pig tails before baking (shown in photo).  I started by piping and flooding the white collar and arm band detail.  Once dried, I piped and flooded the red dress.  I allowed the dress to dry over night.  The next day, I added flesh toned legs, arms, and face.  I added the button and waist sash detail.  I piped white socks and black shoes on once the flesh toned icing was dry.  For Annie's hair to achieve highlighted look, I used orange and red icing and swirled them together.  I used pink luster dust to make her cheeks rosy.  Final touch was to pipe on black eyes and a red smile.

For Annie's dog, I used a cookie cutter similar to this one.  I piped and filled the dog with brown icing that was a bit thicker than flood-type icing.  I used a 1 inch flat paint brush and pounced it in the icing to create fur texture.  Once that layer of icing had dried, I added more in a few spots and repeated the same technique.  Finally I added eyes, nose and ear.

I used this plaque for the "The sun will come out tomorrow" cookie.  I started out by piping and flooding the plaque white and letting it dry.  I used my Silhouette to create a sun stencil.  I purchased this shape and cut of the sun.  I laid the stencil on top of the dried cookie and sprayed it with yellow color mist.  Then I piped the words on with black icing.  The final touch was piping a yellow border on the cookie.

The dress cookie cutter is from here.  I started out by piping and flooding the white collar and sleeves.  Once those two sections were dry, I piped and flooded the dress with red icing.  I allowed the red icing to dry overnight and then added the white buttons and sash at the waist.

For the taxis, I used the car cookie cutter from this set.  I drew in the wheels and windows with a food coloring marker.  Then I piped over them with light blue and black icing.  Once those sections had dried I piped and flooded the taxi yellow.  Then I added a black line and the word "TAXI".  The final touches were yellow hubcaps, fenders and a light grey bumper.