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22. Pedro Almodovar/Penelope Cruz
Notable Collaborations: "Live Flesh," "All About My Mother," "Volver," "Broken Embraces"
What makes them special: Cruz is easy to dismiss because she is almost absurdly beautiful, but a few times over the course of her career, directors have taken chances on her and she has proven to be far more than just a perfect surface. She may have won her Oscar working for Woody Allen, but there is no moment better for her in any film than the scene where she sings in "Volver." Almodovar, like George Cukor elsewhere on this list, has a particular gift for directing women, and you could make the case for Camen Maura's work with him as another all-time-great pairing of filmmaker and actor. But Cruz was born to be a movie star, and Almodovar is still the one who has best showcased her gift.