I will discuss the nature of a population of dusty, luminous galaxies at z~2 discovered by the Spitzer Space Telescope. Application of a simple optical to mid-IR color criterion (F_24um/F_0.7um > 1000) to Spitzer wide-field surveys efficiently identifies a significant fraction of the IR-luminous z~2 population. These objects, known as dust-obscured galaxies (DOGs), may be related to sub-millimeter selected galaxies (SMGs) within an evolutionary paradigm for massive galaxies at z~2. I will present a multi-wavelength study of DOGs aimed at testing this hypothesis, including results from (1) CSO 350um single dish and CARMA 1mm interferometry imaging; (2) HST NICMOS morphologies; and (3) stellar population synthesis modeling of optical through mid-IR photometry. Within the evolutionary paradigm for massive galaxies, these observations imply the mid-IR bright phase (DOGs) occurs subsequent to the sub-millimeter bright phase (SMGs). I will discuss some future directions, focusing on extending these studies to the most massive, luminous galaxies in the universe via EVLA and ALMA follow-up observations of sources selected from the Wide-field IR Survey Explorer mission.