Skidmore graduated in political science and philosophy in 1954 from Denison University. He received a Fulbright Fellowship to study philosophy at Oxford University where he met his wife Felicity. He received a second B.A. in Philosophy, Politics and Economics in 1956 and a master's degree in 1959. He obtained his Ph.D. at Harvard University in 1960 with a thesis on the German Chancellor Leo von Caprivi.[1]
His attention shifted to South America after the Cuban Revolution. His Harvard post-doctorate focused on Brazil. In 1967 he published Politics in Brazil: 1930-64, An Experiment in Democracy.[1]
In 1966, Skidmore joined the faculty of the University of Wisconsin, Madison. He became a full professor in 1968. In 1986, Skidmore moved to Brown University.[1]

"Politics in Brazil became an instant classic. Its detached, elegant narrative and wide array of sources on the history of twentieth-century Brazil compelled Brazilian historians, who had until then focused on the colonial era, to confront the complexities of the politically decisive republican period."--