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The paper deals with the first decades in the work of Dr. Seuss (the pseudonym of Theodor Geisel, 1904–1991), one of the most prominent children’s authors of the 20th century. Seuss was not only the author of children’s tales, but also a talented artist who illustrated his own books and whose manner was deeply influenced by his 15-year experience as a cartoonist. In 1920–1940s he worked for different print media, from humor magazines to a political newspaper, drew cartoons and commercial advertisements. Our aim is to study the mutual influence of Seuss-thecartoonist and Seuss-the-writer and illustrator. Our main focus is the “bestiary” of Dr. Seuss, the animal characters of his cartoons and tales. Seuss created his first eccentric animals in the series of cartoons and anecdotes for a weekly satirical magazine Judge in 1927; he blended the Victorian tradition of nonsense and the features of newspaper cartoons and comic strips of the first decades of the 20th century. The motif of eccentricity is developed in the first children’s tales that Seuss published at the turn of the 1930–40s. The same motif is significantly transformed in his political cartoons for a daily newspaper PM in 1941–1942. Seuss puts the familiar animal images into the context of World War II and gives them different political meaning, from the totalitarian insanity of the Axis leaders to the carelessness and blindness of the “America First” supporters. Interestingly enough, Dr. Seuss used in his political cartoons some plot elements of his tales for children, as well as his old sketches and drawings. In its turn, his post-war tales are peculiar parables that absorb the political issues of the previous historical period. Creating his images of tyrants, Seuss makes use of the techniques of political cartoons. He puts his human and animal characters into the situations of tyranny or isolationism, that can be overcome with the help of common sense.