Rosten is best remembered for his stories about the night-school "prodigy" Hyman Kaplan (first published in The New Yorker in the 1930s, and later reprinted in two volumes—The Education of H*Y*M*A*N K*A*P*L*A*N and The Return of H*Y*M*A*N K*A*P*L*A*N, under the pseudonym Leonard Q. Ross).