The last decade (2013–2023) was the most prolific period of organic Rankine cycle (ORC) research in history in terms of both publications and citations. This article provides a detailed review of the broad and voluminous collection of recent internal combustion engine (ICE) waste heat recovery (WHR) studies, serving as a necessary follow-on to the author’s 2013 review. Research efforts have targeted diverse applications (e.g., vehicular, stationary, and building-based), and it spans the full gamut of engine sizes and fuels. Furthermore, cycle configurations extend far beyond basic ORC and regenerative ORC, particularly with supercritical, trilateral, and multi-loop ORCs. Significant attention has been garnered by fourth-generation refrigerants like HFOs (hydrofluoroolefins), HFEs (hydrofluoroethers), natural refrigerants, and zeotropic mixtures, as research has migrated away from the popular HFC-245fa (hydrofluorocarbon). Performance-wise, the period was marked by a growing recognition of the diminished performance of physical systems under dynamic source conditions, especially compared to steady-state simulations. Through advancements in system control, especially using improved model predictive controllers, dynamics-based losses have been significantly reduced. Regarding practically minded investigations, research efforts have ameliorated working fluid flammability risks, limited thermal degradation, and pursued cost savings. State-of-the-art system designs and operational targets have emerged through increasingly sophisticated optimization efforts, with some studies leveraging “big data” and artificial intelligence. Major programs like SuperTruck II have further established the ongoing challenges of simultaneously meeting cost, size, and performance goals; however, off-the-shelf organic Rankine cycle systems are available today for engine waste heat recovery, signaling initial market penetration. Continuing forward, next-generation engines can be designed specifically as topping cycles for an organic Rankine (bottoming) cycle, with both power sources integrated into advanced hybrid drivetrains.