Apply creme foundation to each actor. Choose a foundation one shade darker than the actor's normal skin color. Begin on the forehead and work up into the hairline, then cover the face. Blend foundation all the way down the neck so there are no lines and the actor's features stand up under the light.
Highlight the cheekbones with either blush or lighter foundation, then create shadows or highlights as appropriate for the character. The Dorothy character should have normal face makeup, so creme blush on the cheekbones. The Lion character should use a lighter creme makeup on the cheekbone, then shadows under the cheekbone to define the cheeks. Widen the nose with lighter creme along the bridge and sides. For the Scarecrow character, use a neutral highlighter three shades lighter than the foundation makeup on the cheeks. The focal point of the scarecrow is the brown nose, so the rest of the makeup is chosen from a neutral palette. For the Wicked Witch Evillene, use blush high on the cheeks, then darker shadows under the cheekbones to sharpen the face. Narrow the nose by using darker makeup, about three shades darker than the foundation, along the sides of the nose.
Use eyeliner to outline the eyes of each character. The main characters of Dorothy, the Tin Man, the Lion and the Scarecrow should have a brown eyeliner running from the inside to the outside corner of the eye on the top lid. Shadow the lids in a neutral color just lighter than the foundation. For Evillene, use a heavy application of black, liquid eyeliner on the top and bottom lids. Extend the line slightly on the inside and outside corner of the eyes. Use heavy mascara to accentuate the lashes, or add fake lashes.
Apply neutral or light brown lip coloring to Dorothy's three friends. Outline the lips lightly in a neutral color. Rely on accessories and hair to complete the look of these characters. The foundation makeup should be simple. Dorothy should use a rose lip color with lip liner and gloss. Evillene needs heavy red or black lip coloring, with age lines over the upper lips to sharpen the look. Feather eye liner pencil in vertical lines from the bottom of the nose to the upper lip to create the shadows.
Add or create a mane on the Lion by using a wig or braiding the hair. Dreadlocks on a wig or natural dreadlocks make a good look for the Lion. Use facial hair as well. The Lion should have a mustache, and may have a shaped beard as well. The Scarecrow should have a large, brown nose. Make it with rubber, or use brown makeup. The movie version resembled a round candy wrapper, but use creativity to make a distinct face for the scarecrow. His hair should spike out, either with a wig or with his natural hair moussed or gelled into place. If the character is played by an African-American, use an afro look. For the Tin Man the hair is not as important as the accessories. Use silver wires, headphones, cameras, CDs and other metallic materials to create a headpiece and facial accessories. Use silver makeup to draw lines in patterns resembling computer chips, or go for a cleaner look with just a few metallic accents. To create Evillene, use metallic, futuristic fabrics for an elaborate headpiece, or go with a grittier look using black fabric. Consider accents on her face as well, using jewels or feathers to create the wicked witch look.
Finish the makeup by applying powder with a makeup brush.