Shenker enrolled at the University of Pennsylvania (UPenn) for college but interrupted his studies to serve with the Army Air Corps in World War II.
Among the notable figures he interviewed and profiled over the years were Isaac Asimov, Jorge Luis Borges, Fernand Braudel, Noam Chomsky, M. C. Escher, Al Hirschfeld, John Kenneth Galbraith, Graham Greene, Alf Landon, Marcel Marceau, Groucho Marx, Vladimir Nabokov, S. J. Perelman, Pablo Picasso, Menachem Mendel Schneerson, Isaac Bashevis Singer, and Aleksandr Solzhenitsyn.
In the latter half of his career, Shenker was known in particular for his coverage of letters, lexicography and languages, especially Yiddish, to which he retained an ardent lifelong attachment.
In later years, in ostensible retirement, he wrote freelance articles for The New York Times on European travel.
[4] His work also appeared in other magazines from Sports Illustrated to American Heritage, and he intermittently authored "Talk of the Town" pieces and other articles for The New Yorker from the 1960s to the 1980s.