By early 1888 Russell had begun illustrating magazines and books. He eventually worked on volumes by Theodore Roosevelt, Bret Harte, and Owen Wister. For the 1911 edition of The Virginian, Russell contributed forty-three drawings. Concerning this phase of Russell’s career, Donald A. Barclay wrote in Dictionary of Literary Biography, “Although he did good work illustrating the writings of others, some of Russell’s best book and magazine work was done for his own first-person stories of western life. Never a good hand at spelling or grammar, Russell was nevertheless a master storyteller. He was so gifted, in fact, that it is often said that when Russell and his friend Will Rogers were together in a roomful of people, it was Rogers who took a back seat to listen while Russell amused the crowd with his droll tales of cowpunching and western life . . . . It was only natural for Russell to illustrate his stories when he eventually took on the laborious task of writing them. Like his paintings, Russell’s oral and written stories were based in part on his own experience, in part on stories he had heard, and in part on his nostalgia for the frontier. Whatever the subject of the story, Russell’s ear for dialogue and his sense of humor came through.” 

Writing---inscriptions, poems, letters, or published stories---was not an easy undertaking for Russell. He eventually began to use images to express himself on paper. This he termed “paper talk.” In this mode, rules of grammar, spelling and punctuation did not apply. Historian Brian Dippie in Charles M Russell, Word Painter observed that Russell “reserved his highest praise for writers . . . . He modeled and drew with ease but labored so mightily to put his thoughts on paper that he was convinced writing was a higher gift.” Gradually Russell’s self-confidence grew, but the process remained difficult. In writing the now legendary tales that appeared in the Rawhide Rawlins Stories and other publications, Russell would struggle with his pencil and paper with Nancy Russell or Percy Raban (a friend who was a journalist and one of the founders of the Montana Newspaper Association) eventually taking down his thoughts as Russell talked. The character of Rawhide Rawlins is an old cowboy who narrated or quoted others to relate his tales. These yarns appeared in various Montana newspapers between 1916 and 1921. In the early 1920s Russell gathered the stories into a volume and the Montana Newspaper Association published them. Rawhide Rawlins appeared in 1921 and More Rawhides was printed in 1925. Russell insisted that the volume be priced at one dollar to be therefore affordable to Montanans who were already suffering from drought and economic recession. A reporter from Great Falls recounted a conversation with Russell, “These are hard times for a lot of folks . . . .  If this book is going to give anybody a laugh and make him forget his troubles for a while, I want the price low enough so that people to whom a dollar means a dollar will feel that they’re getting their money’s worth.” The Rawhide Rawlins stories were well received but were not as financially successful as had been expected.

In 1926, the year of his death, Russell was working on the stories and illustrations for his second book, Trails Plowed Under. The volume was completed the following year by Nancy Russell and published by Doubleday, Page and Company. Trails Plowed Under contained eight stories that Russell had newly written, thirty-three tales reprinted from Rawhide Rawlins Stories and More Rawhides, and an introduction by Will Rogers. Trails Plowed Under was successful with the public and with literary critics. Since its publication in 1927, it has remained almost continually in print. 

Nancy Russell in 1929 published 145 of her husband’s illustrated letters in a volume entitled Good Medicine, a title chosen she explained, “because they bring a kindly thought or laugh.”  She also wrote a biographical section and Will Rogers again contributed the introduction. Good Medicine was another success and was an immediate favorite with Russell admirers. The charm of the volume, however, was somewhat diminished by the decision to present the text of most of the letters in typeset format instead of Russell’s handwriting. An additional problem was that several of Russell’s friends declined to loan their numerous letters to Nancy Russell for inclusion in the book. Brian Dippie expressed, “Charlie Russell sprang back to life from the pages of Good Medicine---droll, wise, charming, a painter in words as well as pigments. No book will ever supplant it in the affection of Russell’s multitude of admirers.”