In addition to writing and drawing the Skippy strip, Crosby wrote several books based on the character, and they grew increasingly ruminative, political, and odd. After the first Skippy novel for young readers, Crosby wrote Dear Sooky, a collection of letters from Skippy to a dead little friend of his in heaven. Its follow-up, Skippy Rambles, was a collection of short essays of political and social comment written in an erratic voice, part Crosby, part Skippy, part speaking in tongues. With his next book, A Cartoonist’s Philosophy, Crosby largely abandoned Skippy and rambled, for the most part incoherently, about economics, religion, politics, racketeering, and taxes. Since no publisher would take the book, Crosby had it printed himself. In a typical section, Crosby writes:
I believe that it is the Divine Will that the whole structure will eventually crash, because it has been erected on a foundation of hypocrisy and greed. Out of the chaos the real leaders will rise; leaders who are not interested in wealth nor political power, but who have been ordained by a higher power to lift humanity from discord to the realms of harmony. Then a new race will be born to the world, here in America, and their worship of God will be built on science and philosophy through the great corridors of Universal Brotherhood.
More self-published books and pamphlets followed through the late thirties, all of them dealing in part with Crosby’s conviction that Franklin Roosevelt, in conspiracy with Stalin, was transforming the United States into a totalitarian Socialist state. Crosby submitted article-length versions of his ramblings to the major newspapers (including The Washington Post, The Washington Herald, and The New York Times); when they were rejected, he paid to have them published in the same papers as full-page and double-spread ads. As Robinson reported in his book, Crosby spent more than $30,000 on these advertisements in a single year.
Crosby lost his syndication contract for “Skippy” in 1945. Four years later, after a failed suicide attempt, he was taken to Bellevue, then transferred for long-term care to the psychiatric ward at Kings Park Veterans’ Hospital on Long Island, where he remained until he died, on his seventy-third birthday, in 1964. What happened to Crosby? Robinson, struggling in the last pages of his book to come to terms with Crosby’s decline, found an easy answer: “genius is an enigma.”