Pintor de pin-ups durante más de 20 años para calendarios y publicidad, con gran sentido artístico e imaginación.
Para su primer trabajo en 1947, para Kelly-Springfield’s Celebrity Tires, Medcalf pintó una hermosa niña que paseaba a su perro en una finca, con un coche deportivo en el fondo, Entonces, Dorman. Products (fabricantes de piezas de automóviles) quiso algo parecido para su publicidad y Medcalf creó una imagen impresionante de una niña y su perro con un picnic en frente de un automóvil.
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