In recent years, two approaches have emerged for the analysis of character evolution: the largely statistical “convergence” approach and the mainly cladistic “homology” approach. I discuss the strengths and weaknesses of these approaches as they apply to phylogenetic analyses of life-history variation in birds. Using examples from analyses of character variation in swallows, I suggest that the phylogenetic approach yields distinctive insights into the selective role of the environment and other characters of the organism on the evolution of life-history traits. This view thus has the potential of bringing together micro- and macro-evolutionary views of life-history evolution.