Several popular Shakespearean characters are dramatically portrayed on stage with striking physical appearances caused by medical and dermatologic disorders. Shakespeare's colorful portrayal of their maladies not only helps to entertain audiences but also serves to define the characters' personalities and behavior. Shakespeare himself emphasizes this point in his play Richard III, in which the notorious English king states that his evil nature is a direct result of his hideous spinal deformity. This contribution discusses four other famous Shakespearean characters: Bardolph, who appears to be suffering from rosacea; the Witches of Macbeth, who have beards; Juliet, who has green sickness (chlorosis); and Falstaff, who is morbidly obese. In all of these cases, their skin disorders and medical maladies serve to highlight their underlying nature.