Two-dimensional flow past an infinitely long cylinder of nanoscopic radius in superfluid 4 He at zero temperature is studied by time-dependent density functional theory. The calculations reveal two distinct critical phenomena for the onset of dissipation: 1) vortex-antivortex pair shedding from the periphery of the moving cylinder and 2) appearance of cavitation in the wake, which possesses similar geometry as observed experimentally for fast moving micrometer-scale particles in superfluid 4 He. Vortex pairs with the same circulation are occasionally emitted in the form of dimers, which constitute the building blocks for the Benard-von Karman vortex street structure observed in classical turbulent fluids and Bose-Einstein condensates (BEC). The cavitation induced dissipation mechanism should be common to all superfluids that are self-bound and have a finite surface tension, which include the recently discovered self-bound droplets in ultracold Bose gases.PACS numbers: 67.25.dg,67.25.dk, 67.85.-d One of the manifestations of 4 He superfluidity at zero temperature (T ) is the frictionless liquid flow through capillaries at sufficiently low velocities. Based on the well-known Landau criterion, the onset of dissipation is related to the unusual form of the superfluid dispersion relation, ǫ(p), which exhibits roton minimum ǫ(p min ) at p min . The flow should become dissipative when the velocity reaches the critical Landau value v L = ǫ(p min )/p min = 59 m/s [1]. Similarly, an object moving in superfluid 4 He should experience drag only above a certain critical velocity threshold v c . It is well established experimentally that objects moving already at much lower velocities than v L experience drag due to the emission of non-linear excitations in the form of quantized vortices; see for example Ref. [1].Multiple interacting vortices in a superfluid can form a well-defined lattice or a more complicated vortex tangle, depending on their geometry and circulation. At high vortex densities, vortex reconnection events, which are believed to be responsible for the large-scale behavior of quantum turbulence [2-5], become increasingly important. Quantum turbulence is associated with the proliferation of quantized vortices [6,7]. From the experimental point of view, vorticity can be created by stirring or rotating the superfluid [8][9][10].Although quantized vorticity plays a key role in the onset of dissipation in superfluid flows, a fundamental understanding of their role in exerting drag on moving objects and the dependence of the associated critical velocity on the object size is still lacking. In this paper, we identify a new, previously overlooked, energy dissipation mechanism that takes place also well below v L . The energy loss and the induced drag force on the object in this mechanism originate from the formation of cavitation bubbles in the wake. Cavitation bubbles play a crucial role in the appearance of drag as they may act as vortex nucleation seeds through local distortions of their surface and, more importa...