Comprehension and corpus studies have found that the tendency to minimize dependency length has a strong influence on constituent ordering choices. In this paper, we investigate dependency length minimization in the context of discriminative realization ranking, focusing on its potential to eliminate egregious ordering errors as well as better match the distributional characteristics of sentence orderings in news text. We find that with a stateof-the-art, comprehensive realization ranking model, dependency length minimization yields statistically significant improvements in BLEU scores and significantly reduces the number of heavy/light ordering errors. Through distributional analyses, we also show that with simpler ranking models, dependency length minimization can go overboard, too often sacrificing canonical word order to shorten dependencies, while richer models manage to better counterbalance the dependency length minimization preference against (sometimes) competing canonical word order preferences.