Direct detection and characterization of Earth-like planets around Sun-like stars is a core task for evaluating the prevalence of habitability and life in the Universe. Here, we discuss a promising option for achieving this goal, which is based on placing an occulter in orbit and having it project its shadow onto the E-ELT at the surface of Earth, thus providing a sufficient contrast for imaging and taking spectra of Earth-like planets in the habitable zones of Sun-like stars. Doing so at a sensible fuel budget will require tailored orbits, an occulter with a high area-to-mass ratio, and appropriate instrumentation at the E-ELT. In this White Paper, submitted in response to the ESA Voyage 2050 Call, we outline the fundamental aspects of the concept, and the most important technical developments that will be required to develop a full mission.