Discontinuous quantum phase transitions and the associated metastability play central roles in diverse areas of physics ranging from ferromagnetism to false vacuum decay in the early universe. Using strongly-interacting ultracold atoms in an optical lattice, we realize a driven many-body system whose quantum phase transition can be tuned from continuous to discontinuous. Resonant shaking of a one-dimensional optical lattice hybridizes the lowest two Bloch bands, driving a novel transition from a Mott insulator to a $\pi$-superfluid, i.e., a superfluid state with staggered phase order. For weak shaking amplitudes, this transition is discontinuous (first-order) and the system can remain frozen in a metastable state, whereas for strong shaking, it undergoes a continuous transition toward a $\pi$-superfluid. Our observations of this metastability and hysteresis are in good quantitative agreement with numerical simulations and pave the way for exploring the crucial role of quantum fluctuations in discontinuous transitions.