Spatially extensive and persistent drought episodes have repeatedly influenced human history, including the 'Strange Parallels' drought event in monsoon Asia during the mid-18th century. Here we explore the dynamics of sustained monsoon failure using observed and tree-ring reconstructed drought patterns and a 1300-year pre-industrial community earth system model control run. Both modern observational and climate model drought patterns during years with extremely weakened South Asian monsoon resemble those reconstructed for the Strange Parallels drought.