The present paper addresses the swing equation with additional delayed damping as an example for pendulum-like systems. In this context, it is proved that recurring sub-and supercritical Hopf bifurcations occur if time delay is increased. To this end, a general formula for the first Lyapunov coefficient in second order systems with additional delayed damping and delay-free nonlinearity is given. In so far the paper extends results about stability switching of equilibria in linear time delay systems from Cooke and Grossmann and complements an analysis of Campbell et al., who consider time delay in the restoring force. In addition to the analytical results, periodic solutions are numerically dealt with. The numerical results demonstrate how a variety of qualitative behaviors is generated in the simple swing equation by only introducing time delay in a damping term.The swing equation is, e.g., at the core of any power system model. By delayed frequency control it becomes a pendulum equation with delayed damping -a system which is shown to exhibit highly complex dynamics. Repeating Hopf bifurcations lead again and again to the emergence of limit cycles as delay is increased. These limit cycles undergo further bifurcations including period doubling cascades and the birth of invariant tori.