In this book chapter, I describe two artistically and scientifically motivated experiments created in the Republic of Côte d'Ivoire over a period of 28 years, as well as the first official portrait of a European monarch made by an African artist. My own work, (1999), corresponds with a mask portrait experiment (1972) by the German anthropologist Hans Himmelheber (1908-2003). The predominant gaze is similarly challenged in an earlier work, the portrait of Queen Elizabeth II by Nigerian artist Odinigwe Benedict Chukwukadibia Enwonwu (1917-1994) from 1956, which is also discussed. The volume contains contributions by: Ebenezer Kwabena Acquah and Isaac Opoku-Mensah, Jane Otieno, Mary Clare Kidenda, Rashida Resario, Melisa Achoko Allela and Odoch Pido, Alexis Malefakis, Stefan Eisenhofer, Mark Evans, Njeri Gachihi, Frauke Gathof, Clara Himmelheber, Lydia Nafula, Bea Lundt, Benjamin Merten, Esther Kute and Odoch Pido, Lize Kriel, Lydia Muthuma and Fred Mbogo, Amanda du Preez, Ernst Wagner and Sokari Douglas Camp, Runette Kruger, Avitha Sooful, Paul-Henri Souvenir Assako Assako, Angelika Boeck, Ronnie Watt.