Macroscopic frictional behavior of granular materials is of great importance for studying several complex problems associated with fault slip and landslides. The main objective of this study is to model the macroscale frictional behavior of granular soils under monotonic and cyclic loadings based upon micromechanical determination of dissipated energy at particle contacts. This study is built on the general observation that the externally computed energy dissipation should be equal to the total internal energy dissipation derived from inter-particle sliding and rolling, energy losses from inter-particle collisions, and damping. For this purpose, the discrete element method is used to model a granular soil and determine the stored, dissipated, and damping energies associated with shear loading for applied monotonic and cyclic velocities. These energies are then related to the friction by an application of the Taylor-critical state power balance relationship. Also, the contributions of the different modes of energy dissipation (normal, shear, and rolling) to the total frictional resistance were studied. By changing the inter-particle friction, the simulations showed that the macroscopic friction was nearly constant, the slip friction increased almost linearly with increasing inter-particle friction, and the difference between the two was attributed to the non-energy dissipating dilatancy component. By providing a clear relationship between energy dissipated by micro-scale mechanisms versus the traditional engineering definition based on macro-scale (continuum) parameters, this study provides a means to develop a better understanding for the frictional behavior of granular media.