[1][2] He was the son of Margaret Isaphene McGehee and Alexander Madison Whittington, a farmer.

He moved to Roxie, Mississippi on January 1, 1901 where he was principal of a school and also started practicing law.

[3] In January 1904, he moved to Greenwood, Mississippi, where he continued the practice of law and also started cotton farming.

[2] While with the legislature, he showed his prohibitionist leanings when he authored the state's first Bone Dry Law.

[1][2] Due to Jim Crow laws, Whittington was elected to the House by just 4,000 people, despite living in a district of 435,000.

[3] In 1940 and, again, in 1941, Whittington wanted to run for the United States Senate, but was talked out of it by friends.

[1] He retired in 1951 and returned to Greenwood where he practiced law with his son Whittington Jr.[1][3] He served as delegate to the Democratic National Conventions in 1920, 1928, 1936, 1940, and 1948.