Throughout geological time, an intertwined relationship between ecology and evolution has enabled distant clades to attain gigantism. By synthesizing fossil and modern data, we identify key tipping points in the rise of extreme-sized ocean animals—from early Cambrian arthropods and Ordovician mollusks to Triassic ichthyosaurs, Neogene sharks, and Quaternary whales. We show that ecological opportunities—from vacant niches to shifts in ocean productivity—have promoted the evolution of key adaptations to enhance prey intake, such as predatory appendages, specialized dentition, and baleens, ultimately enabling species to reach extreme sizes. The presence of ocean giants, in turn, has reshaped marine food webs, energy flow, nutrient cycling, and overall ecosystem structure. As such, their extinction or decline can have profound and lasting ecological consequences. Understanding the coevolutionary dynamics between marine giants and their environments is essential for predicting their resilience and conserving their critical roles in ocean ecosystems.