The air-breathing fishes have heuristic importance as possible models for the Paleozoic evolution of vertebrate air breathing and the transition to land. A recent hypothesis about this transition suggests that the diverse assemblage of marine amphibious fishes occurring primarily in tropical, high intertidal zone habitats are analogs of early tetrapods and that the intertidal zone, not tropical freshwater lowlands, was the springboard habitat for the Devonian land transition by vertebrates. Here we argue that selection pressures imposed by life in the intertidal zone are insufficient to have resulted in the requisite aerial respiratory capacity or the degree of separation from water required for the vertebrate land transition. The extant marine amphibious fishes, which occur mainly on rocky shores or mudflats, have reached the limit of their niche expansion onto land and remain tied to water by respiratory structures that are less efficient in air and more vulnerable to desiccation than lungs. We further argue that evolutionary contingencies actuated by the Devonian origin of the tetrapods marked a critical point of divergence for a way of life in which selection pressures would operate on the physiology, morphology, and natural history of the different vertebrate groups. While chronically hypoxic and shallow water conditions in the habitats of some primitive bony fishes and some amphibians appear similar to the conditions that prevailed in the Devonian, markedly different selection pressures have operated on other amphibians and bony fishes over the 300 million years since the vertebrate land transition. For example, both egg development and larval metamorphosis in extant amphibians are geared mainly toward compensating for the uncertainty of habitat water quality or even the absence of water by minimizing the time required to develop there. In contrast, reproduction by most intertidal (and amphibious) fishes, all of which are teleosts, remains dependent on a planktonic larval phase and is characterized by specializations (brooding) that minimize overdispersal and maximize recruitment back to the littoral habitat.