Cultivated plants that cannot survive on their own often have maladaptive domestication traits. Unharvested crop seeds may generate feral populations, at times causing serious weed problems, but little is known about the evolution of ferality. We explored the potential for cultivated radish, Raphanus sativus, to become feral, given that closely related taxa (e.g., R. raphanistrum and crop–wild hybrids) are well-documented weeds. First, we measured the population growth of five experimental, cultivated, self-seeding radish populations in Michigan, USA, for three generations. Three late-flowering populations went extinct, and two others apparently hybridized with local R. raphanistrum. A common garden experiment showed that the two surviving populations had earlier flowering, smaller root diameters, and greater individual fecundity than did nonhybridized populations. We also used artificial selection to measure the evolutionary potential for earlier flowering. After two generations of strong selection, two of three lineages flowered earlier and produced more seeds than control lineages, but insufficient genetic variation prevented dramatic evolution of crop phenotypes. In summary, it seems unlikely that radishes could spontaneously become feral in our study area without gene flow from R. raphanistrum. Applying these approaches to other cultivated species may provide a better understanding of mechanisms promoting the evolution of feral weeds.