 From 1928 to 1937, Crosby produced 3,650 "Skippy" strips, ten books of fiction, political and philosophical essays, drawings and cartoons, as well as numerous pamphlets, while also mounting a dozen exhibitions in New York City, Washington, D.C., London, Paris and Rome of his oils, watercolors and other paintings and drawings.With its success, he befriended a pantheon of famed creators, including the author Marc Connelly, the humorist Robert Benchley, "The New Yorker" editor Harold Ross, "Life" magazine editor and future Pulitzer Prize-winning playwright Robert E. Sherwood, and the cartoonists and painters George McManus, H. T. Webster and Guy Hoff.Crosby's marriage to Gertrude Volz had become strained during the 1920s, and after a few years of legal separation the two were divorced in 1927.