Morton next headed to Chicago, a town where he would eventually make a name for himself, but where nothing was happening upon his first visit. He also traveled to Houston, and finally out to California before returning for his last visit to New Orleans, where he took up with a gentleman named Jack the Bear. The two lit out across the South selling a unique tuberculosis cure: Coca-Cola spiked with salt. All the while, Morton was playing piano when he could, and no doubt absorbing all the music he encountered along the way. He encountered Hispanic music on his trips into Texas and to California (not to mention Tijuana), and he later told Alan Lomax that it was impossible to play jazz without any Latin flavor. He played in minstrel shows, turning up in Chicago again, and St. Louis. Then it was back to California, arriving in Los Angeles in 1917, where he and a woman named Anita Gonzalez ran hotels and nightclubs. Some say it was Gonzalez who bought Morton the large diamond he wore in his front tooth, pawning it whenever he desperately needed money. Next, Morton was in Denver, playing with bandleader George Morrison.

Years later, there were plenty who doubted Jelly Roll's accounts of all the placed he had been and the things he had seen. However, his accounts have largely proven to be true, as have some of his more verifiable claims. Though he may or may not have "invented" jazz, he certainly was instrumental in moving music from the rather mechanical two-step feel of ragtime to something approaching swing. Many saw him as an anachronism, an embarrassing holdover from the distant days of New Orleans when what would become jazz music was inextricably bound up with brothels, card cheats, and the tall tales of the carny. It would be wrong to deny that he had a very strong sense of self and a pretty good dose of self-esteem, even that he was a braggart. But so much of what he claimed for himself has turned out to be true that it is sad to see how much he suffered because of what others took to be outright lying.

The fact is that he wrote tunes such as "New Orleans Blues" and "Jelly Roll Blues" around 1905, "King Porter Stomp" in 1906, and "Georgia Swing" in 1907, as he took pains to point out in a 1938 letter to a Baltimore newspaper, a letter that was also printed in Downbeat magazine. As guitarist Lawrence Lucie said of Morton:

"Jelly was a walking encyclopedia, and he was very entertaining. He always smiled after he said something outrageous. He knew exactly what he wanted in his music, and he believed in his style. Some people thought he was old-fashioned, but he was greater than we all thought he was. He'd been ahead of his time for a long time before times caught up to him."

Indeed, by 1923, when Morton arrived in Chicago, times had changed. Sheet music was becoming a large industry, and for those who composed popular tunes, like Morton, there was money to be made. Previously, musicians had been scared of publication (and sometimes recording, too) fearing that other musicians would be able to steal their best riffs and tricks. But now there was simply too much money to be made to ignore, and Jelly Roll Morton was sitting on a goldmine of musical compositions.