South Asia is home to one of the fastest-growing populations in Asia, and human activities are leaving indelible marks on the land surface. Yet the likelihood of successive observed droughts in South Asia (SA) and its four subregions (R-1: semi-arid, R-2: arid, R-3: subtropical wet, and R-4: tropical wet and dry) remains poorly understood. Using the state-of-the-art self-calibrated Palmer Drought Severity Index (scPDSI), we examined the impact of different natural ocean variability modes on the evolution, severity, and magnitude of observed droughts across the four subregions that have distinct precipitation seasonality and cover key breadbaskets and highly vulnerable populations. The study revealed that dryness had significantly increased in R-1, R-2, and R-4 during 1981–2020. Temporal analysis revealed an increase in drought intensity for R-1 and R-4 since the 2000s, while a mixed behavior was observed in R-2 and R-3. Moreover, most of the sub-regions witnessed a substantial upsurge in annual precipitation, but a significant decrease in vapor pressure deficit (VPD) during 1981–2020. The increase in precipitation and the decline in VPD partially contributed to a significant rise in Normalized Difference Vegetation Index (NDVI) and a decrease in dryness. In contrast, a strong positive correlation was found between drought index and precipitation, and NDVI across R-1, R-2, and R-4, whereas temperature and VPD exhibited a negative correlation over these regions. No obvious link was detected with El-Niño Southern Oscillation (ENSO) events, or Indian Ocean Dipole (IOD) and drought evolution, as explored for certain regions of SA. The findings showed the possibility that the precipitation changes over these regions had an insignificant relationship with ENSO, IOD, and drought onset. Thus, the study results highlight the need for considering interactions within the longer climate system in describing observed drought risks rather than aiming at drivers from an individual perspective.