The evolutionary relationships of the eutherian order Insectivora (Lipotyphla sensu stricto) are the subject of considerable debate. The difficulties in establishing insectivore phylogeny stem from their lack of many shared derived characteristics. The grouping is therefore something of a ‘wastebasket’ taxon. Most of the older estimates of phylogeny, based on morphological evidence, assumed insectivore monophyly. More recently, molecular phylogenies argue strongly against monophyly, although they differ in the extent of polyphyly inferred for the order. I review the history of insectivore phylogenetics and systematics, focussing on the relationships between the six extant families (Erinaceidae – hedgehogs and moonrats, Talpidae – moles and desmans, Soricidae – shrews, Solenodontidae – solenodons, Tenrecidae – tenrecs and otter-shrews and Chrysochloridae – golden moles). I then examine how these various phylogenetic hypotheses influence the results of comparative analyses and our interpretation of insectivore life-history evolution. I assess which particular controversies have the greatest effect on results, and discuss the implications for comparative analyses where the phylogeny is controversial. I also explore and suggest explanations for certain insectivore life-history trends: increased gestation length and litter size in tenrecs, increased encephalization in moles, and the mixed fast and slow life-history strategies in solenodons. Finally, I consider the implications for comparative analyses of the recent strongly supported phylogenetic hypothesis of an endemic African clade of mammals that includes the insectivore families of tenrecs and golden moles.