Lipid bilayers assembled on solid substrates have been extensively studied with single-molecule resolution as the molecules diffuse in 2D, however the out-of-plane motion is typically ignored. Here we present sub-nanometer out-of-plane diffusion of nanoparticles attached to hybrid lipid bilayers (HBLs) assembled on metal surfaces. The nanoscale cavity formed between Au nanoparticle and Au film provides strongly-enhanced optical fields capable of locally probing HBLs assembled in the gaps. This allows us to spectroscopically resolve the nanoparticles assembled on bilayers, near edges, and in membrane defects, showing the strong influence of charged lipid rafts. Nanoparticles sitting on the edges of the HBL are observed to flip onto and off the bilayer, with flip energies of ~10 meV showing how thermal energies dynamically modify lipid arrangements around a nanoparticle. We further resolve the movement of individual lipid molecules by doping the HBL with low concentrations of Texas-red (TxR) dye-labeled lipids.