Before reconciling the disparate physics of these systems, we first assessed the viability of several methods for quantitatively comparing surface hydrophobicity, including calculation of (i) nanoscale contact angles via structural analysis, (ii) excess chemical potentials via thermodynamic integration, and (iii) dehydration free energies via indirect umbrella sam-pling. The simulations generally yielded a hydrophobic ordering for amorphous polymers (PTFE PE > PVC > PMMA > N66 > PVA) that is commensurate with experimentally measured contact angles. Dynamical characterization of interfacial water revealed that water molecules were typified by longer structual decorrelation times when in proximity to PMMA, N66, and PVA surfaces versus in proximity to PTFE, PE, or PVC. Furthermore, characteristic relaxation times of water dynamics, particularly associated with rotational decorrelation of water in the interfacial layer, was highly correlated with calculated metrics of nanoscale hydrophobicity. The broad agreement of hydrophobic orderings from these distinct calculation methods suggests that the simulations capture essential physics, major and subtle, that distinguish the wettability of distinct polymer surfaces.