Islands are natural laboratories to study how species evolve in novel environments. In Madagascar, a biodiversity hotspot with an exceptional diversity of endemics, several lineages of birds have undergone this experiment with varying results. Of the 50+ lineages that have colonized the island, only half have subsequently diversified within the island. We use Madagascar as a model system to study comparable endemic birds on a single landmass and investigate the influence of timing, space, and phylogeny on diversification patterns. Our studies indicate a complex dynamic of dispersal into Madagascar from nearby Africa as well as more distant landmasses. Some groups, like the vangas and tetrakas, demonstrate adaptive radiations with dramatically different phenotypic diversification than their non-Malagasy relatives. Additionally, detailed phylogeographic analyses within Madagascar have uncovered hidden diversity and evidence for fine-scale patterns of micro-endemism for birds. Our studies continue to grow knowledge of diversification patterns in this under-studied region with modern genomic and phenomic tools.