His career spanned more than five decades, including multiple gubernatorial bids, legislative service, and roles in academia and business.

[6] He graduated from Tyler Consolidated High School in 1939[1][3] and later enrolled at Salem University in Harrison County, where he was student body president and a member of Sigma Phi Epsilon fraternity.

[4] During World War II, he served as an Army Reservist before returning to teach high school biology in St. Marys, West Virginia (1943–1946).

[1] At just 22 years old, Underwood launched his political career by winning a seat in the West Virginia House of Delegates in 1944.

Following the lead of Governor William C. Marland, the Democrat who preceded him in office, Underwood continued the desegregation of West Virginia schools without violent confrontation at all levels and was a supporter of civil rights legislation.

He later advocated an organized civil service and retirement pension system, and provided temporary employment relief for low-income families.

[8] Because West Virginia's constitution prohibited governors from serving consecutive terms at that time, Underwood ran for the United States Senate in 1960, but was defeated by incumbent Democrat Jennings Randolph.

[1] During the 1960s, he was named temporary chairman of the Republican National Convention and was once considered for the office of Vice President under Richard Nixon.

[5] He continued his academic career by serving as President of Bethany College[5] and instructor of political science at Marshall University.