Car operation requires advanced brain function. Currently, evaluation of the motor vehicle driving ability of people with higher brain dysfunction is medically unknown and there are few evaluation criteria. The increase in accidents by elderly drivers is a social problem in Japan, and a method to evaluate whether elderly people can drive a car is needed. Under these circumstances, a system to evaluate brain dysfunction and driving ability of elderly people is needed. Gaze estimation research is a rapidly developing field. In this paper, we propose the gaze calculation method by eye and head angles. We used the eye tracking device (TalkEyeLite) made by Takei Scientific Instruments Cooperation. For our image processing technique, we estimated the head angle using the template matching method. By using the eye tracking device and the head angle estimate, we built a system that can be used during actual on-road car operation. In order to evaluate our proposed method, we tested the system on Japanese drivers during on-road driving evaluations at a driving school. The subjects were one instructor of the car driving school and eight general drivers (three 40–50 years old and five people over 60 years old). We compared the gaze range of the eight general subjects and the instructor. As a result, we confirmed that one male in his 40s and one elderly driver had narrower gaze ranges.