The picture-winged species Drosophila grimshawi is unique among Hawaiian Drosophila in its wide geographic range, having populations on several islands of the Hawaiian archipelago. This distribution contrasts with the pattern of single-island endemism observed in most of the picture-winged group; significantly, it does not concur with predictions of the founder theory, where speciation is the typical outcome of founder events involving colonization of a new island. To examine this anomalous situation, we have taken a phylogenetic approach in an attempt to resolve the relationships among taxa and decipher the most probable colonization scenario. We have obtained both morphological and molecular data for all the D. grimshawi populations as well as the closely related species D. pullipes, and two outgroup species, using scanning electron microscopy to score ultrastructural features of the chorion or eggshell, and PCR amplification and nucleotide sequencing to acquire sequence data on Yp1, one of the three Yolk protein genes. In addition, we have used available data on Yolk Protein electrophoretic pattern and jousting, oviposition, and mating behavioral characters. Analyses of these data sets, either individually or in combination, indicate that there are two separate and ecologically distinct clades within this species complex. One clade includes the Kauai and Oahu populations of grimshawi, as well as the closely related species D. pullipes from Hawaii, all of which are classified as ecological specialists with respect to their oviposition and breeding substrate. The other clade includes all the ecologically generalist grimshawi populations of the Maui Nui island complex. The phylogenetic results do not concur with the previously proposed hypothesis that D. pullipes originated from a founder derived from the Maui Nui complex and further suggest that these taxa are in need of taxonomic revision.