Anderson, a Pennsylvania native, taught himself to fly by watching other pilots. Then, in 1941, first lady Eleanor Roosevelt visited the Army Air Corps base at Tuskegee Institute, Alabama. Anderson was asked to fly Roosevelt around for almost an hour. Many aviation historians credit this short flight as the inspiration for training the first African-American military pilots, many of whom would go on to serve their country as members of the 332nd Fighter Group, which would later be known throughout the world as the Tuskegee Airmen.

Anderson would become the group’s chief flight instructor.

More than 950 black servicemen were trained as pilots at Tuskegee. In March 1942, five of the first cadets received their "wings." One of these men, Benjamin Oliver Davis Jr., became the leader of the Airmen.

Davis was a natural for the role. He was the first black to graduate from West Point and would later become the first black three-star general.

Under Davis’ leadership, the squadron proved to be a dangerous opponent to the enemy. The Airmen completed 1,578 missions throughout Northern Africa and Europe, shooting down enemy planes, bombing enemy trains and escorting fighter pilots to their missions.

The American bomber pilots called the Airmen the "redtail angels" because they painted the tails of their planes red and, more importantly, they never lost a pilot they were assigned to escort.