Throughout his career, Thurber's fiction often reflected elements of his personal experiences. Most of his contributions to the New Yorker appeared during the 1930s, with his earlier stories exhibiting a more playful and innocent tone. However, his writing adopted a darker edge during his troubled marriage to Althea, which ended in divorce in June 1935. Just a month later, he married Helen Wismer. This period overlapped with major social upheavals, such as World War II and the McCarthy Era, both of which he openly criticized.

In addition to these challenges, Thurber suffered from serious health issues, undergoing multiple surgeries and struggling with worsening blindness, which eventually led to an emotional breakdown. The stories he crafted during these challenging times are marked by their terrifying, bitter, and harsh qualities. Works like "The Cane in the Corridor" (published on January 2, 1943, and later included in The Thurber Carnival in 1945) exemplify this darker side of Thurber. These stories delight in cruel pranks and others' misfortunes, signaling a shift away from conventional humor.

Despite the passage of time, Thurber's exceptional humor remains unparalleled, and he consistently delivered top-notch comedic fiction throughout his career. One of his early pieces for the New Yorker, "The Night the Bed Fell," ranks among his best works. Part of the 1933 series "My Life and Hard Times" (originally published on July 8 and later included in a hardcover collection of the same name), this story highlights the semi-autobiographical and semi-fictional style that Thurber perfected. It narrates a comical series of events and misunderstandings that supposedly took place one night during his childhood in Columbus. The humor escalates as each incident builds on the previous one, with the pace quickening as the story progresses.