Bifurcations and chaos of a three-dimensional single-loop feedback system with a discontinuous piecewise linear feedback function are examined. Chaotic attractors are generated at the same time of the destabilization of foci accompanied with grazing. Multiple periodic solutions are connected with homoclinic orbits based at a pseudo saddle-focus, which satisfies the condition of Shil’nikov chaos formally. The generation of chaotic oscillations is shown in a circuit experiment on a linear ring oscillator with a comparator. The homoclinic bifurcations and chaos are also shown in a ring neural network with a nonmonotonic neuron.