In open quantum systems, dissipative phase transitions (DPTs) emerge from the interplay between unitary evolution, drive, and dissipation. While second-order DPTs have been predominantly investigated theoretically, first-order DPTs have been observed in single-photon-driven Kerr resonators. We present here an experimental and theoretical analysis of both first and second-order DPTs in a two-photon-driven superconducting Kerr resonator. We characterize the steady state at the critical points, showing squeezing below vacuum and the coexistence of phases with different photon numbers. Through time resolved measurements, we study the dynamics across the critical points and observe hysteresis cycles at the first-order DPT and spontaneous symmetry breaking at the second-order DPT. Extracting the timescales of the critical phenomena reveals slowing down across five orders of magnitude when scaling towards the thermodynamic limit. Our results showcase the engineering of criticality in superconducting circuits, advancing the use of parametric resonators for critically-enhanced quantum information applications.