The author discusses his work creating programmable, generative analogue drawing machines over six decades in the context of the constructivist tradition and influenced by the Bauhaus German art school and the subsequent art, science, and technology movement. During the first three decades he developed a variety of machines and from 1990 followed a more analytical approach focusing on randomness, chaos, and subjectivity in art. This progressed to the author’s PhD research program wherein he investigated innovative analogue programming systems that employed direct current motors, linkages, and cranks together with programmers, actuating motors for a variety of timed pulses. These enabled variables such as pen-lift and rotation, forward/reverse pen action, light drawing, sine waves, turntable and drum machines, and versions of X:Y plotters.