Hybridization has played an important role in the evolution of many lineages. With the growing availability of genomic tools and advancements in genomic analyses, it is becoming increasingly clear that gene flow between divergent taxa can generate new phenotypic diversity, allow for adaptation to novel environments, and contribute to speciation. Hybridization can have immediate phenotypic consequences through the expression of hybrid vigor. On longer evolutionary time scales, hybridization can lead to local adaption through the introgression of novel alleles and transgressive segregation and, in some cases, result in the formation of new hybrid species. Studying both the abundance and the evolutionary consequences of hybridization has deep historical roots in plant biology. Many of the hypotheses concerning how and why hybridization contributes to biological diversity currently being investigated were first proposed tens and even hundreds of years ago. In this Update, we discuss how new advancements in genomic and genetic tools are revolutionizing our ability to document the occurrence of and investigate the outcomes of hybridization in plants.