In both the Old and New Worlds, independent clades of sit-and-wait insectivorous birds have evolved. These independent radiations provide an excellent opportunity to test for convergent relationships between morphology and ecology at different ecological and phylogenetic levels. First, I test whether there is a significant adaptive relationship between ecology and morphology in North American and Southern African flycatcher communities. Second, using morphological traits and observations on foraging behavior, I test whether ecomorphological relationships are dependent upon locality. Third, using multivariate discrimination and cluster analysis on a morphological data set of five flycatcher clades, I address whether there is broad scale ecomorphological convergence among flycatcher clades and if morphology predicts a course measure of habitat preference. Finally, I test whether there is a common morphological axis of diversification and whether relative age of origin corresponds to the morphological variation exhibited by elaenia and tody-tyrant lineages. The general results were this: 1) Morphology significantly predicted the foraging behavior in both NA and SA flycatchers. 2) North American and Southern African communities are concordant with respect to the ecomorphological relationships. 3) I found that there are lineage-specific positions in morphological space when examining synoptic morphological samples of Old and New World flycatcher clades. 4) There were fundamental differences in the orientations of morphological disparity of Old versus New world flycatchers. 5) The results of separate principal components and common principal component analyses reveal a larger morphological volume being occupied by older lineages, but 6) Macroevolutionary patterns exist within constituent clades that are inconsistent with a Brownian motion evolutionary hypothesis. Hence, the differences in morphological disparity observed in flycatchers are most likely due group-specific factors including genetic constraints, ecological limiting similarity and ecological opportunity. Phylogenetic constraints to morphological evolution are not universal throughout the history of flycatcher evolution. Furthermore, historical and/or stochastic factors were equal to ecological factors during flycatcher evolution.