We review the properties of massive star evolution in different environments, where the major environmental factor is metallicity. Comparisons between evolutionary models and observations of massive OB, WR stars and related objects are presented. We also review several observations asking for future improvements of stellar models and theoretical developments in this respect. We summarize evolutionary scenarios for the most massive stars and try to clarify recent questions regarding their evolutionary status as core-H or core-He burning objects. Another environmental effect, which might affect stellar evolution is a cluster environment with a high stellar density. As test cases of massive star evolution in dense clusters we summarize recent work on the densest known resolved young clusters: R136, NGC 3603, and the three Galactic Center (GC) star clusters - the central cluster, Quintuplet and the ``Arches'' cluster. For the central cluster we present new comparisons between stellar parameters of emission line stars derived by Najarro et al. (1994, 1997), and appropriate evolutionary models. From their parameters we argue that most of these stars can be regarded as WNL stars, and do hence not necessarily represent a peculiar class. We suggest that some apparent differences with well known WR stars can be understood in terms of their core burning stage and/or other changes due to a high metallicity. Based on our present knowledge we conclude that in young clusters with central stellar densities up to rhoc ~ 105-6 M_sun pc-3 no compelling evidence for a secondary effect influencing the evolution of massive stars has yet been found.