Over its 37-year history, the Gordon Bell Prize has strongly influenced the development of high performance simulation and big data statistics in mostly positive, but also in some negative, ways, with implications for the operations of leading supercomputer centers. We briefly discuss the evolution of the prize in its several awarded categories then focus on a handful of submissions of influence. For example, driven by insights from Bill Gropp, the 1999 Gordon Bell Special Prize paper that first addressed an unstructured grid PDE application is presented as a pre-cursor of the 2009 roofline model now universally used to assess whether an application is compute- or bandwidth-bound, or even instruction-bound at a finer examination. The flop/s rate orientation of the Prize has encouraged wasteful flops, where a smaller number would provide more cost-effective delivery of quantities of scientific interest to working accuracy; we provide examples from four of our own recent submissions. How to pilot the Prize at the confluence of the roaring rivers of simulation and learning, with the tributary of quantum computing about to join, is the final topic of discussion. As energy costs now dominate what can be simulated and what can be learned or inferred, the elusive metric of “science per Joule” is proposed as one of several aspects to be addressed in the future evolution of this inspiring legacy.