Regrowth after fire is critical to long-term persistence of chaparral shrub communities in southern California. This region is subject to frequent fire, habitat fragmentation, and protracted droughts linked to climatic change. Short-interval fire (SIF) is considered an inhibitor of recovery and cause of “type conversion” in chaparral, based on field studies of small extents and limited time periods. Sub-regional scale investigations based on remotely sensed data, however, suggest that SIF may explain little variance in postfire chaparral recovery. Drought may contribute to poor recovery or worsen the impact of repeated, short-interval fires. Previous studies have not shown whether drought reduces chaparral recovery significantly across the region, while variations in response among community types and climate zones are not well resolved. This research evaluates a regional pattern of chaparral recovery, based on series of Normalized Difference Vegetation Index (NDVI) from annual, June-solstice Landsat images (1984–2018). High resolution aerial images were used in validation and calibration. The main objectives were (1) to assess effects of fire-return interval and number of burns on chaparral recovery using 0.25 km2 sample plots (n = 528) which were paired and stratified for experimental control, and (2) to explain recovery variations across the region based on geospatial climate, vegetation, soil, terrain, and temporal drought metric data (seasonal precipitation, climatic water deficit (CWD), and Palmer Drought Severity Index (PDSI)) from 982 locations. Results suggest that SIF is most impactful in sites that burned three times within 25 years. More substantial effects were observed due to drought. In particular, ecotonal chaparral bounding the Colorado Desert is most subject to drought impact. We also highlight utility in landscape-scale predictors of drought impact on recovering chaparral, including Very Atmospherically Resistant Index (VARI).