Before the age of ten, Countryman appeared in more than a dozen Hollywood films, and afterwards had a brief career on the New York stage.
A graduate of a private Jesuit military secondary school, he served in the Air Force and then entered the Foreign Service in 1962.
[1] Following his 35-year diplomatic career, he served as Executive Director of the Mission for Peace and Cooperation in the Middle East under the auspices of Search for Common Ground.
[2] His father, Russell Countryman, worked for Associated Press as a photography and art editor; his mother was a Czech immigrant.
[a] One of his notable film roles was as Tyltyl, the younger brother of Shirley Temple's character Mytyl in The Blue Bird, released in 1940.
[2][10][11] While in college, Countryman had signed up with the Reserve Officers' Training Corps (ROTC), but his military service was deferred when he was awarded a post-graduate Fulbright Fellowship to study English literature at the Free University of Berlin.
He served primarily in the mainland United States, although he did provide limited support for personnel and equipment transfers between Alaska and Japan.
He successfully passed the written and oral exams in 1961, the same year he received his master's degree in English and American literature with his thesis on "The German Element in the Writings of Thomas Wolfe".
[2] Countryman's posting required him to serve as a general rotation officer in each of the mission's four departments: consular, administrative, economic, and political.
In January 1965 he completed his posting and was assigned to the State Department in Washington, D.C. as a staff aide to Averell Harriman.
[2] In August 1966, Countryman applied for Arabic language training with the intention of concentrating his diplomatic service on one geographic area.
Countryman briefed Democrat and Republican Congressmen on the issues, which included Israel's concern over the supply of American weaponry to Saudi Arabia.
So then the issues came down to just how sophisticated the weaponry is that you sell to Saudi Arabia, and what controls do you put in place so you make sure it is not used against Israel".
He spent much of his time dealing with the Iran hostage crisis through briefing the Saudis and the Gulf States, and working on foreign policy initiatives with other governments and the United Nations.
[21] Countryman developed the growing relationship between the U.S. and Oman by promoting trade as well as military access; his staff coordinated a 150th anniversary celebration of the Treaty of Amity and Commerce between the two nations.
[2] Countryman also hosted a large congressional delegation led by Charles H. Percy, chairman of the Senate Foreign Relations Committee.
He researched and wrote a paper on the subject of "Oil and Security in the Persian Gulf", which he then developed into an all-day seminar for the Foreign Service Institute.
He then worked several years as Executive Director of the Mission for Peace and Cooperation in the Middle East, under the auspices of Search for Common Ground.