Purpose of Review: The purpose of this paper was to address how sleep changes with aging, with the broader goal of informing how REM sleep and slow wave activity mechanisms interact to promote cognitive longevity. Recent Findings: We conducted novel analyses based on the National Sleep Research Resource database. Over approximately 5 years, middle-to-older aged adults, on average, showed dramatically worse sleep fragmentation, a steady decrease in slow wave sleep, and yet a small increase in REM sleep. Averaging across participants, however, masked a major theme: Individuals differ substantially in their longitudinal trajectories for specific components of sleep. We considered this individual variability in light of recent theoretical and empirical work that has shown disrupted sleep and decreased slow wave activity to impair frontal lobe restoration, glymphatic system functioning, and memory consolidation. Based on multiple recent longitudinal studies, we contend that preserved or enhanced REM sleep may compensate for otherwise disrupted sleep in advancing age. Summary: The scientific community has often debated whether slow wave activity or REM sleep mechanisms are more important to cognitive aging. We propose that a more fruitful approach for future work will be to investigate how REM and slow wave processes dynamically interact to affect cognitive longevity. © 2018, Springer Nature Switzerland AG.