We show that the well-known Čerenkov Effect contains new phenomena arising from the quantum nature of charged particles. The Čerenkov transition amplitudes allow coupling between the charged particle and the emitted photon through their orbital angular momentum (OAM) and spin, by scattering into preferred angles and polarizations. Importantly, the spectral response reveals a discontinuity immediately below a frequency cutoff that can occur in the optical region. Specifically, with proper shaping of electron beams (ebeams), we predict that the traditional Čerenkov radiation angle splits into two distinctive cones of photonic shockwaves. One of the shockwaves can move along a backward cone, otherwise considered impossible for Čerenkov radiation in ordinary matter. Our findings are observable for ebeams with realistic parameters, offering new applications including novel quantum optics sources, and open a new realm for Čerenkov detectors involving the spin and orbital angular momentum of charged particles.