By using the worldline Monte Carlo technique, matrix product state, and a variational approach à la Feynman, we investigate the equilibrium properties and relaxation features of the dissipative quantum Rabi model, where a two level system is coupled to a linear harmonic oscillator embedded in a viscous fluid. We show that, in the Ohmic regime, a Beretzinski-Kosterlitz-Thouless quantum phase transition occurs by varying the coupling strength between the two level system and the oscillator. This is a nonperturbative result, occurring even for extremely low dissipation magnitude. By using state-of-the-art theoretical methods, we unveil the features of the relaxation towards the thermodynamic equilibrium, pointing out the signatures of quantum phase transition both in the time and frequency domains. We prove that, for low and moderate values of the dissipation, the quantum phase transition occurs in the deep strong coupling regime. We propose to realize this model by coupling a flux qubit and a damped LC oscillator.