Both Venus and Mars have captured the human imagination during the twentieth century as possible abodes of life. Venus had long enchanted humans—all the more so after astronomers realized it was shrouded in a mysterious cloak of clouds permanently hiding the surface from view. It was also the closest planet to Earth, with nearly the same size and surface gravity. These attributes brought myriad speculations about the nature of Venus, its climate, and the possibility of life existing there in some form. Mars also harbored interest as a place where life had or might still exist. Seasonal changes on Mars were interpreted as due to the possible spread and retreat of ice caps and lichen-like vegetation. A core element of this belief rested with the climatology of these two planets, as observed by astronomers, but these ideas were significantly altered, if not dashed during the space age. Missions to Venus and Mars revealed strikingly different worlds. The high temperatures and pressures found on Venus supported a “runaway greenhouse theory,” and Mars harbored an apparently lifeless landscape similar to the surface of the Moon. While hopes for Venus as an abode of life ended, the search for evidence of past life on Mars, possibly microbial, remains a central theme in space exploration. This survey explores the evolution of thinking about the climates of Venus and Mars as life-support systems, in comparison to Earth.