At leading twist the transverse-momentum dependent parton distributions of the pion consist of two functions, the unpolarized f1,π(x, k 2 ⊥ ) and the Boer-Mulders function h ⊥ 1,π (x, k 2 ⊥ ). We study both functions within a light-front constituent model of the pion, comparing the results with different pion models and the corresponding nucleon distributions from a light-front constituent model. After evolution from the model scale to the relevant experimental scales, the results for the collinear pion valence parton distribution function f1,π(x) are in very good agreement with available parameterizations. Using the light-front constituent model results for the Boer-Mulders functions of the pion and nucleon, we calculate the coefficient ν in the angular distribution of Drell-Yan dileptons produced in pion-nucleus scattering, which is responsible for the violation of the Lam-Tung relation. We find a good agreement with data, and carefully discuss the range of applicability of our approach.