The endosperm develops in fertilized ovules of angiosperms following fertilization of the central cell and nuclei in the female gametophyte. Endosperms differ in whether, and which, nuclear divisions are followed by cellular divisions; the variants are classified as cellular, nuclear or helobial. Functional correlates of this variation are little understood. Phylogenetic methods provide a powerful means of exploring taxonomic variation and phylogenetic patterns, to frame questions regarding biological processes. Data on endosperms across angiosperms were analysed in a phylogenetic context in order to determine homologies and detect biases in the direction of evolutionary transitions. Analyses confirm that neither all nuclear nor all helobial endosperms are homologous, raise the possibility that cellular development is a reversal in some derived angiosperms (e.g. asterids) and show that a statistically significant bias towards evolution of nuclear endosperms (and against reversals) prevails in angiosperms as a whole. This bias suggests strong selective advantages to having nuclear endosperm, developmental constraints to reversals or both. Homologies suggest that the microtubular cycle and cellularization pattern characteristic of reproductive cells across land plants may have been independently co–opted during multiple origins of nuclear endosperms, but information on cellular endosperms is essential to investigate further.