Calochortus and the family Liliaceae s.s. have often been considered each other's closest relatives, based partly on their shared possession of bulbs, visually showy flowers, winged wind-dispersed seeds, and narrow parallel-veined leaves. We present a well-supported molecular phylogeny for these groups and their close relatives in the core Liliales, based on sequence variation in the chloroplast-encoded rbcL and ndhF genes. This analysis identifies Liliaceae s.s. as monophyletic. including one clade (((Lilium, Fritillaris, Nomocharis), Cardiocrinum), Notholirion) that appears to have diversified in the Himalayas roughly 12 million years ago and another ((Erythronium, Tulipa), (Gagea, Lloydia)) that arose in East Asia at about the same time. Medeola and Clintonia are sister to Liliaceae s.s. and bear rhizomes, inconspicuous flowers, fleshy animal-dispersed fruits, and broad reticulate-veined leaves. Calochortus is sister to Tricyrtis; both Tricyrtis and the neighboring clade of Prosartes-Streptopus-Scoliopus share several of the traits seen in Medeola-Clintonia. The core Liliales thus provide compelling examples of both concerted convergence and phylogenetic niche conservatism. Invasion of open, seasonal habitats was accompanied by the independent evolution of bulbs, showy flowers, wind-dispersed seeds, and narrow parallel-veined leaves in Calochortus and Liliaceae s.s. Conversely, persistence in shady habitats was accompanied by the retention of rhizomes, inconspicuous flowers, animal-dispersed seeds, and broad reticulate-veined leaves in their sister groups. We advance arguments for the context-specific adaptive value of each of these traits, as well as evidence of parallel trends in other groups. Concerted convergence--convergence in several different traits, favored by the same shared set of ecological conditions, in two or more lineages--is an important evolutionary process that can mislead evolutionary analyses based solely on phenotypic variation.