Drought conditions significantly impact human and natural systems in the Tropics. Here, multiple observational and reanalysis products and ensembles of simulations from the Coupled Model Intercomparison Project Phase 5 (CMIP5) are analyzed with respect to drought areal extent over tropical land regions and its past and future relationships to the El Niño/Southern Oscillation (ENSO). CMIP5 models forced with prescribed sea surface temperatures compare well to observations in capturing the present day time evolution of the fraction of tropical land area experiencing drought conditions and the scaling of drought area and ENSO, i.e., increasing tropical drought area with increasing ENSO warm phase (El Niño) strength. The ensemble of RCP8.5 simulations suggests lower end-of-the-century El Niño strength-tropical drought area sensitivity. At least some of this lower sensitivity is attributable to atmosphere-ocean coupling, as historic coupled model simulations also exhibit lower sensitivity compared to the observations.