The self-incompatibility (SI) status of 571 taxa from the Asteraceae was identified and the taxa were scored as having SI, partial SI or self-compatibility (SC) as their breeding system. A molecular phylogeny of the internal transcribed spacer (ITS) region was constructed for 211 of these taxa. Macrophylogenetic methods were used to test hypotheses concerning the ancestral state of SI in the Asteraceae, the gain and loss of SI, the irreversibility of the loss of SI and the potential for partial SI or SC to be terminal states. The ancestral breeding system in the family could not be resolved. Both maximum likelihood and parsimony analyses indicated that transitions among all breeding system states provide the best fit to the data and that neither partial SI nor SC is a terminal state. Furthermore, the data indicated that the loss of SI is not irreversible, although breeding system evolution has been more dynamic in some clades than in others. These results are discussed within the context of evidence for the gain and loss of SI, the evolutionary role of partial SI and methodological assumptions of tests of breeding system evolution.