The study of cosmological strong lensing, across a broad range of lens masses and configurations, is changing rapidly. In particular, the development of large lens samples is transforming lensing studies from predominantly one-off papers on individual sources to statistically driven multi-paper studies on well defined samples. In this talk I will describe ongoing work to characterize large cluster-scale lens samples from (primarily) the SDSS, as well as highlight some of the results coming from analysis of these samples. Two primary regimes of study are enabled: the study of the lens population and the underlying generative cosmology, and the study of the lensed background universe, using the lenses as natural telescopes. I will describe recent results on both fronts, concluding by highlighting an HST program happening now that is imaging the largest sample of cluster-scale lenses yet assembled.