Extreme weather events, such as drought, have marked impacts on biotic communities. In many regions, a predicted increase in occurrence of such events will be imposed on landscapes already heavily modified by human land use. There is an urgency, therefore, to understand the way in which the effects of such events may be exacerbated, or moderated, by different patterns of landscape change. We used empirical data on woodland‐dependent birds in southeast Australia, collected during and after a severe drought, to document temporal change in the composition of bird assemblages in 24 landscapes (each 100 km2) representing a gradient in the cover of native wooded vegetation (from 60% to <2%). We examined (a) whether drought caused region‐wide homogenization of the composition of landscape bird assemblages, and (b) whether landscape properties influenced the way assemblages changed in response to drought. To quantify change, we used pairwise indices of assemblage dissimilarity, partitioned into components that represented change in the richness of assemblages and change in the identity of constituent species (turnover). There was widespread loss of woodland birds in response to drought, with only partial recovery following drought‐breaking rains. Region‐wide, the composition of landscape assemblages became more different over time, primarily caused by turnover‐related differentiation. The response of bird assemblages to drought varied between landscapes and was strongly associated with landscape properties. The extent of wooded vegetation had the greatest influence on assemblage change: landscapes with more native vegetation had more stable bird assemblages over time. However, for the component processes of richness‐ and turnover‐related compositional change, measures of landscape productivity had a stronger effect. For example, landscapes with more riparian vegetation maintained more stable assemblages in terms of richness. These results emphasize the importance of the total extent of native vegetation, both overall cover and that occurring in productive parts of the landscape, for maintaining bird communities whose composition is resistant to severe drought. While extreme climatic events cannot be prevented, their effects can be ameliorated by managing the pattern of native vegetation in anthropogenic landscapes, with associated benefits for maintaining ecological processes and human well‐being.