Painter, printmaker, journalist and writer Cyrus Leroy Baldridge was born May 27, 1889, in Alton, New York. His parents divorced when he was very young, and his mother took up a door-to-door traveling sales route, bringing Baldridge along and giving the young artist an appreciation of the nomadic lifestyle that he would carry with him throughout his career. 

His mother eventually settled in Chicago, marrying artist Frank Holmes when Baldridge was ten years old. Under Holmes' tutelage he flourished in the field of drawing, learning how to create quick sketches of figures and facial expressions on the street and apply his observations to more detailed works in Holmes' studio. With this knowledge, Baldridge applied to the University of Chiacgoin 1907; he was accepted, and he paid his way through sign painting for the University's campus events. The commercial experience proved useful after graduation, when, after a few years as a National Guardsman and work as a cow hand, he was given a position as a war correspondance illustrator upon the commencement of World War I. Using a German letter of passage, he traveled by bicycle, horse cart, and foot through many beleagured European territories, recording what he saw. 

His experience as a correspondant during war time included being called up by the National Guard in 1916 to travel to the U.S./Mexico border and record the battle between the U.S. Army and Pancho Villa; he then joined the French Army as a stretcher-bearer, but was then transferred by the U.S. government to the American Expeditionary Forces as chief artist for the Stars and Stripes newspaper when the U.S. entered World War I. These experiences led to the artist's peace and freedom of speeach activism throughout his career. 

Beginning in 1920 Baldridge and his companion Caroline Singer decided to embark on a trip throughout the African continent and into Asia, beginning with Sierra Leone and across to Ethiopoia, then India, China, and Japan. These visits became a great source of inspiration to Baldridge, who sketched the people and places they met and ventured through. When the pair returned to the United States, Baldridge began seeking out African American thinkers and artists, and was commissioned to illustrate the works of some of the Black writers he came to know. He and Singer published several books about their travels and Baldridge's activism expanded to vocally protest mounting sentiments of race inferiority as Europe barreled toward a second world war. 

In addition to the friendships and connections found along their journey, Baldridge also discovered a love of printmaking after extended periods of time in Japan. He worked with Watanabe Shozaburo who taught him the art of woodcuts, and with this knowledge Baldridge began exploring other forms of printmaking on his return to the States. 

The 1930s '40s proved to be a particularly prolific time for the artist, who in addition to his own fine art was illustrating over 100 publications and books, including his own autobiography, Time and Chance, published in 1947. With the success of this book as well as a profitable job with the Information Please Almanac he and Caroline were able to retire in 1951. They relocated to Santa Fe, living in a small adobe house where Baldridge began to focus primarily on oil painting. Singer, though a successful writer who had intended to focus on her craft once they had settled, developed what was thought to be dementia and later speculated to be a series of small strokes; she died in 1963. 

Baldridge continued to paint and was an active participant in the Santa Fe arts scene until the mid 1970s, when age began to deplete his abilities. He died of a self-inflicted gun shot in 1977. He donated the bulk of his estate to the University of Chicago, much of which can be found at the school's Smart Gallery.