Cutlip was born in Buckhannon, West Virginia, the son of Okey Scott Cutlip and Janet Munson. He was raised by his uncle George Carper Reger. Cutlip started in newspapers with the "Buckhannon Record" in 1933. Moving to Morgantown, West Virginia in 1935, he worked for the West Virginia Newspaper Publishing Company for three years. In 1939 he obtained a bachelor's degree in journalism and political science from Syracuse University. His career in public relations began in 1941 with the West Virginia State Road Commission. In Madison, Wisconsin he continued to study journalism and political science, earning a master's degree from the University of Wisconsin. In 1942 he entered the United States Army Air Forces, where he served with the Fifth Air Force from Australia.