Calvin L. Woolsey, was a man of many talents that went beyond piano rag composition, and occupies a very unique niche in ragtime history. He was not only born to but delivered by his father, Napoleon Bonaparte Woolsey, and mother Gertrude Isabel Minton. While some texts show his birth year as 1884, the hospital record, filled in by his father, is clearly 1883, and other historical sources confirm this year. Calvin was born and raised in Tinney Grove, Missouri, about 3 miles south of Braymer and 60 miles northeast of Kansas City. He had two siblings, Cardinal Boone (1/1882) and Bertella "Bertie" L. (2/1886).

Calvin appears to have had a high intellect and was a fast learner. As of the 1900 census he was shown as a teacher at age 16. He entered the University of Missouri at Columbia in mid-1902 at age 18. After receiving a medical degree he did some post-graduate work at Harvard University, and then returned to Braymer. He was shown in 1908 as a contributor to the Caldwell County Medical Society.. Calvin practiced briefly with his father and brother, but Napoleon died before 1910. The 1910 census showed Calvin living with his widowed mother and sister in Davis, near Braymer, working as a physician with his own office. Gertie was a milliner with her own hat shop.

Woolsey had a brief flash of success as a ragtime composer, turning out six numbers from late 1909 through 1911. After his first rag, Funny Bones, he released four in 1910, including his most popular work, Medic Rag. The sinister sounding Poison Rag also made a splash, but Medic Rag found its way onto far more piano rolls. Having self-published his works, Calvin ended up selling the copyright for Funny Bones and Medic Rag to mega-publisher Jerome H. Remick. The rest of his works came out under the C.L. Woolsey Music Company in Braymer, including one "coon" song, Dissatisfied, with lyrics by the composer. Mashed Potatoes, published by Woolsey in 1911, also did fairly well and saw good distribution in spite of being self-published. There were one or two pieces released each of the following three years. While not all of the titles were medically related, they all showed some wit and creativity in their themes.

The duties of being a doctor finally overtook the art of ragtime composition. In 1913 Calvin moved west to St. Joseph, Missouri, and went to work as an assistant physician at Missouri State Hospital #2. His specialty at Harvard had been that of mental hygiene, a form of psychiatry focused on insanity and other mental issues. By 1915 he was listed in the Institutional Care of the Insane in the United States in the State Hospital, and was earning $1,500 per annum. After his cycle was up in 1916, Woolsey moved eastward to Chillicothe, Missouri to continue his practice and research. According to the Chillicothe Constitution of August 25, 1917,

Woolsey was inducted into the Army Medical Corps on September 11, 1917. In the end, it appears that he did not go to France, but ended up at Camp Kearney near San Diego, California. It was from there that he submitted and copyrighted his final composition, a waltz titled Hearts Across the Sea, in February 1918. Calvin was soon moved to The Presidio in San Francisco, California. He was listed there in the 1920 census as a Captain in the Army Medical Corps. The doctor received an honorable discharge that year as a First Lieutenant.

Returning to Braymer, Missouri, Calvin spent the rest of his life there as a general practitioner M.D. There are reports of him as the typical country doctor with the horse and buggy and wire chicken cages to receive "payment" for farm house calls. However, there may be more quaint legend to this than truth as the Model T Ford was the most likely conveyance used by doctors in that time. Calvin had many other interests as well, and was known to be a very fine cook and a carpenter as well, building or improving some of his properties. In the mid-1920s he became fascinated with radio, and was able to assemble receivers from components. In 1930 he was still living with his mother and sister in Braymer, having never married, and was listed as a General Practitioner. Gertie was still running her hat shop.

In 1934 Woolsey was elected Vice President of the Caldwell-Livingston County Medical Society, and remained in important roles in that organization for the next decade. Gertrude Woolsey died in January, 1935. For the 1940 enumeration Calvin and Bertie were still residing together in the family home, with C.L. listed as a medical doctor with a private practice. Calvin Lee Woolsey was found dead in his garage on November 12, 1946, a victim of coronary thrombosis just short of his 63rd birthday. Fortunately his great Missouri folk rags with the wry wit saw a rebirth in the 1970s, and are still played more than a century after they were composed.