They opened a knitting shop in the Greater Lawndale area of Chicago, where Rosten and his younger sister grew up among other working-class Jewish families.

Rosten showed an interest in books and language very early and began writing stories when he was only nine.

During the Great Depression, when he was unable to find other work, he taught English for recent immigrants at night.

These experiences eventually became the source of his most popular works, 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. Rosten studied political science, economics, and psychology at both the University of Chicago, where he obtained his doctorate in political science, and the London School of Economics.

[1] From this time date his life-long friendships with Milton Friedman, W. Allen Wallis and other economists who would become influential in forming American neoliberalism.

[4] After the war, his connection with Allen Wallis led to his involvement with forming the Social Sciences division at the RAND Corporation.

Rosten is best remembered for his stories about the night-school "prodigy" Hyman Kaplan, written under the pseudonym Leonard Q. Ross.

[14] In his book The Joys of Yiddish, he defines the word chutzpah as "that quality enshrined in a man who, having killed his mother and father, throws himself on the mercy of the court because he is an orphan."

In his novel Silky, he defines "nebbish" as "The kind of person, when he leaves a room, you have the feeling someone fascinating just walked in."

Carrie followed in her grandfather's literary footsteps and has written three books, including a young adult novel, Chloe Leiberman (Sometimes Wong).

His obituary in The Independent on February 21, 1997, written by Chaim Bermant, describes his personality as follows:[20] Rosten was an inveterate Anglophile.

He had enjoyed his years at LSE, was amazed by the enthusiastic reception Kaplan had received in the English press, and returned to London whenever opportunity dictated and even when it didn't.