In high school, Toole, as editor of the school newspaper, had written, under a pseudonym, a column of gossip and wit,
Fish Tales, and while at Tulane he worked on the college newspaper, the
Hullabaloo, writing articles, reviewing books, and drawing cartoons. The cartoons were noted for their subtlety and sophistication. Around this time, Toole began associating with a local blues band that performed at high schools, in the
French Quarter, and in the
Irish Channel. Because Toole's classmates and family looked down on the French Quarter as being for tourists and the Irish Channel as a place for lowlifes, Toole kept his trips to those places a secret. His closest friend was guitarist Don Stevens, nicknamed "Steve Cha-Cha," with whom he bonded over their shared love of blues music and
Beat poets. Stevens also had a side job pushing a hot
tamale cart around town and, on days when he was unavailable for work, Toole would fill in for him. According to Stevens's bandmate Sidney Snow, Toole loved eating the tamales. Toole later used these experiences as material for his novel
A Confederacy of Dunces, whose protagonist Ignatius J. Reilly pushes a hot dog cart around town, usually eating most of the profits. Also, like Reilly, Toole later worked at a family business that manufactured men's clothing, Haspel Brothers. He worked for J. B. Tonkel, who married one of the Haspel daughters. "Ken watched the Haspels' business dealings with great interest, absorbing and remembering their troubles and intrigues," He enrolled in
Columbia University in New York on a
Woodrow Wilson Fellowship to study English literature. He took on a heavy workload so that he could earn his master's degree in a single year. In his free time he dated Ruth Kathmann, another student from Tulane, who was studying journalism at Columbia. The couple would go dancing at the
Roseland Ballroom, as the $2.00 entrance fee allowed them to dance all night and suited their limited budget. Toole was considered a talented dancer. There is some question as to whether they were engaged, with friends claiming they were but Kathmann saying only that Toole asked her to marry him, but she declined. After he returned to New Orleans they rarely saw each other, and she married another man. This year is generally considered one of the happiest of his life. While at USL he rented a dilapidated apartment from an elderly and eccentric widow on Convent Street. Toole described the apartment as a "
Conradian metaphor" to friends. Because he was saving for a return to Columbia to get his PhD, Toole was a notorious skinflint during his year at USL. His friends noticed this and forced him to pay for and throw a party at his home. The party was a success and generally considered the best party thrown that year. In contrast to this image of an outgoing, lively young man, when Toole's mother came to visit, friends noticed that he became sullen and withdrawn. His friend Pat Rickels commented that Thelma "was absolutely convinced that he was without flaw and that all the hopes of the world lay in him. It was an extreme form of maternalism, where all your pride and all your hopes are in one person. He had to grow up with that burden. She was a very ostentatious, shrill, loud-voiced, bossy, bragging woman." with
the Wheel of Fortune from a medieval manuscript of a work by
Boccaccio. Fortuna, as interpreted by
Boethius in his
Consolation of Philosophy, was a favorite subject of Toole's
A Confederacy of Dunces protagonist Ignatius J. Reilly. It was at USL that Toole met Bob Byrne, an eccentric English professor who is considered one of the primary inspirations for the character of Ignatius J. Reilly. Byrne specialized in the medieval period, and he and Toole frequently discussed the philosopher
Boethius and the wheel of
Fortuna, as described in Boethius's
Consolation of Philosophy. Boethius was the favorite philosopher of Ignatius J. Reilly, who frequently referred to Fortuna and
Consolation of Philosophy. Like Ignatius, Byrne was a self-admitted devoted slob who played the lute, and also wore a
deerstalker hunting cap, which Toole frequently chided him about. On several occasions while listening to her music with friends he enigmatically remarked, "Is Frances Faye God?" In May 1960, Toole accepted a three-year fellowship to study for a PhD in Renaissance literature at the
University of Washington at Seattle. However, when he was offered a teaching position at
Hunter College in New York, which suited his desire to study at Columbia, he chose Hunter instead. At 22, he became the youngest professor in Hunter's history. Although he pursued a doctorate at
Columbia, he became unhappy with his PhD. He, however, wrote to Fletcher that he still liked Hunter, "principally because the aggressive, pseudo-intellectual, 'liberal' girl students are continuously amusing." Fletcher surmised that based on these girls, he created the character Myrna Minkoff for
A Confederacy of Dunces. Toole, although generally only a "Christmas-and-Easter churchgoer," "Every time the elevator door opens at Hunter, you are confronted by 20 pairs of burning eyes, 20 sets of bangs and everyone waiting for someone to push a Negro," he is reported to have said. Both women said their relationships with Toole never progressed beyond the level of a good night kiss. ==Military service==