The study of multi-body asteroid systems has a significant impact on key questions in planetary astronomy. From analysis of the orbits of satellites around a primary asteroid, fundamental physical characteristics can be directly measured, and the abundance and orbital properties of binaries and triples can reveal much about their formation, evolution, and dynamical environment. Our investigations of both near-Earth triple asteroids 2001 SN263 and 1994 CC and main belt triple Sylvia have elucidated their orbital and physical properties as well as dynamical evolution. These multi-body asteroid systems are also local laboratories for studying dynamics on a much different scale: multi-planet systems. The in-depth dynamical and statistical characterization of multi-planet systems have allowed for a more substantial understanding of the architecture of planetary systems, and have also led to fundamental clues about planet formation and evolutionary processes. By fitting models to data from the Kepler mission, we found that multi-planet systems are typically flat with low relative inclinations and many of them are dynamically packed. The scientific diversity of knowledge gleaned from studying the dynamics of systems with different scales (from asteroids to exoplanets) has the common theme of using N-body dynamics to inform us about the orbital architecture of individual systems and to illuminate the properties of an ensemble of systems as a whole.