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Van der Waay studied at the Amsterdam State Academy. He was educated there from 1871 to 1875. After his education, he shared a studio for some time with his classmate Jan Hillebrand Wijsmuller (1855-1925). In 1880 he won the Willink van Collen Prize for his painting Among friends. In the early eighties, he and his childhood friend Ernst Witkamp (1854-1897) - who was also a student of Koopman - moved into a workshop on Koningsplein. Later Van der Waay owned a studio on the Rozengracht. Van der Waay was the only one to compete for the Prix de Rome in 1883, but because of the lack of competition he was not awarded this prize. August Allebé, however, provided him with a ministerial subsidy of one thousand guilders for a study trip through Italy. He was a teacher at the Rijksakademie for over 30 years and together with Allebé he took care of the painting class. Since 1891 he held a professorship at the State Academy, succeeding Prof. Bart Wijnveld. He held this position until his retirement in 1927. One of his most famous works is Kerkgang van Burgerweesmeisjes, painted around the beginning of the 20th century, which is kept in the Amsterdam Museum. Every Sunday, the civilian orphans went in a long procession from the Burgerweeshuis to the Westerkerk on the Prinsengracht or to the Nieuwe Kerk on Dam Square. Van der Waay made a series of drawings and paintings after existing models, dressed in their typical red and black clothing. At the end of the nineteenth century he became strongly influenced by his fellow painter Isaac Israels and his painting touch became looser and his style more impressionistic. His range of subjects also closely matches that of Israels. Like Israëls, Van der Waay was a master of capturing cityscapes and mundane scenes, often with women in the leading role. Various museums in the Netherlands own work by Van der Waay, including the Rijksmuseum in Amsterdam and Museum Boijmans Van Beuningen in Rotterdam. Van der Waay also drew illustrations for books, such as for the girl's book Het betooverde ravine door Cora (pseudonym of C. van Berckel-van Heek), published in 1895. In 1915 he produced a watercolor for the Liber amicorum of Coenraad Kerbert, the then director of Artis. Van der Waay, just like Witkamp and Wijsmuller, belonged to the secret artists' society MAB; an abbreviation that stood for the initials of the painter Michel Angelo Buonarotti they admired. He was also an honorary member of the "Rembrandt" Society, a society for art and art desires, founded by Jan de Boer (1877-1946) on 28 October 1922 in Amsterdam. In addition to De Boer, nine other artists were members of this association. One of the aims of the Society was to bring art to the common man at affordable prices. Van der Waay's most important pupils were: Lizzy Ansingh, Tjeerd Bottema, Johannes Elsinga (from 1915 to 1918), Henri Goovaerts, Harry Koolen (from 1922 to 1926), Piet Mondriaan (in 1892 and 1893), Paul Rink, Jan Sluijters (during one academic year, from October 1901 to July 1902).