Born in New Orleans to a prominent family, Cunningham was the son of Milton Joseph Cunningham and Cunningham's second wife, the former Anne Peyton. His mother died of tetanus when he was ten months old and is interred in New Orleans. He was thereafter reared in Natchitoches, where he graduated from what is now Northwestern State University. He became a highly regarded educator but left the field to study law. Admitted to the bar, he ran for a district judgeship at the age of twenty-nine but was narrowly defeated. He then served on the Natchitoches Parish Police Jury, the parish governing body now known as the Natchitoches Parish Commission. In 1903, he founded The Natchitoches Times, which he edited until 1930. Cunningham's father, Milton Joseph Cunningham, was a political figure in Natchitoches, DeSoto Parish, and New Orleans, where he spent his later years. After service in both houses of the state legislature, he became the Attorney General of Louisiana, a position which he filled from 1884 to 1888 and again from 1892 to 1900. In 1898, Cunningham married Alicia Evelena Payne, a daughter of William Edward Payne and the former Marie Eliza Blanchard. Alicia's brother, John William Payne, was the sheriff of Natchitoches Parish from 1914 until his death in 1933. Her nephew, William "Bill" Payne, followed his father as sheriff. Mrs. Cunningham, known in her later years as "Miss Lena, continued to publish the paper after her husband's death. She too was a graduate of Northwestern State University and the 1893 class valedictorian. She taught school for a time in Tallulah in Madison Parish in northeastern Louisiana and in Lecompte in south Rapides Parish. During World War II, she was cited for the work of The Natchitoches Times in promoting drives for scrap iron and aluminum. U.S. President Franklin D. Roosevelt recognized her work in promoting the sale of war bonds. The Cunninghams had six other children, Charles Milton Cunningham, Jr., Joseph Blanchard Cunningham, Anna Mary Cunningham, John Hamilton Cunningham, killed in the Battle of the Bulge in Belgium in World War II, Charles Murray Cunningham, and Roman Catholic Sister Elisabeth Cunningham, based at the Our Lady of the Lake Convent in San Antonio, Texas. Cunningham, his wife, and other relatives are interred at Catholic Cemetery in Natchitoches.
