This chapter explores two delightfully unique, flightless seabirds: the Galápagos cormorant, one of the world’s most unusual organisms, and the Galápagos penguin, the only penguin to swim in the Northern Hemisphere. Three themes stand out: first, in pre-settlement Galápagos, neither species suffered great disadvantage because of flightlessness. Having no terrestrial predators allowed both species to nest on land near water’s edge, to specialize in diving for prey in the rich, cool Cromwell upwelling, and to prosper during over a million years of flightless life in Galápagos. Second, from very different evolutionary origins, the two seabirds evolved a fascinating evolutionary convergence in the archipelago—not their flightlessness per se, because penguins were already flightless when they arrived. Instead, there are striking similarities in their uniquely opportunistic mating practices, including the cormorant’s very unusual facultative polyandry. Third, does the older flightless specialist, the penguin, have the advantage when El Niño causes food supply to falter, or does the advantage go to the cormorant, the seabird specifically retooled by evolution for conditions in Galápagos? Forty years of census data show that penguins react slightly more quickly to ENSO and with more population flux, but that both species show impressive reproductive resilience.