Theoretically predicted evolutionary phases of massive close binaries are compared with the observations. For the evolution up to the High-Mass X-ray Binary (HMXB) phase there is fair agreement between theory and observation. Beyond the HMXB phase there is much uncertainty. Notably it is puzzling why we observe so few systems consisting of a helium star and a neutron star (Cygnus X-3 is the only one found so far), and why the incidence of double neutron stars is so low. A better understanding of Common Envelope evolution is required in order to answer these questions. The role of velocity kicks imparted to neutron stars during supernova collapse is discussed. Such kicks might cause many runaway OB stars to be single.