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We describe and experimentally evaluate a method for automatically clustering words according to their distribution in particular syntactic contexts. Deterministic annealing is used to find lowest distortion sets of clusters. As the annealing parameter increases, existing clusters become unstable and subdivide, yielding a hierarchical ``soft'' clustering of the data. Clusters are used as the basis for class models of word coocurrence, and the models evaluated with respect to held-out test data.