Plants transitioned from an aquatic to a terrestrial lifestyle during their evolution. On land, drought became one of the major problems they encountered, as it impacts correct cell functioning necessary to support life. The evolution of morpho-physiological and molecular adaptations to cope with and tolerate drough was undeniably useful to survive on land. Some of these adaptations appeared repeatedly in phylogenetically distant species, showing a signature of convergent evolution. Details of this convergent evolution are now being assessed thanks to recent developments on high throughput phenotyping and whole genome and transcriptome sequencing. Phylogenomic (comparative genomic) and comparative transcriptomic analyses are revealing complex, well-coordinated and intricate gain and loss of genes and co-option of gene regulatory networks underlying cell and tissue specific adaptations to moderate and extreme drought in phylogenetically distant species. Here we review recent research on signatures of convergent evolution of regulatory networks underlying carbon concentrating mechanisms such as C4 and CAM photosynthesis, desiccation tolerance in seeds and resurrection plants, and impermeabilization of root exodermis.