Abstract: We present a thorough analysis of unpolarized Drell-Yan (DY) pair production in pion-nucleus scattering. On the nucleus side, we use nuclear parton distributions along with parametrisations of the nucleon partonic transverse distribution available in the literature. Partonic longitudinal and transverse distributions of the pion are those obtained in a recent calculation in a Nambu-Jona Lasinio (NJL) framework, with Pauli-Villars regularization. The scale of the NJL model is determined with a minimisation procedure comparing NLO predictions based on NJL evolved pion distributions to rapidity differential DY cross sections data. The resulting distributions are then used to describe, up to next-to-leading logarithmic accuracy, the transverse momentum spectrum of dilepton pairs up to a transverse momentum of 2 GeV. With no additional parameters, fair agreement is found with available pion-nucleus data, confirming the virtues of the NJL description of pion parton structure. We find sizable evolution effects on the shape of the distributions and on the generated average transverse momentum of the dilepton pair. We furthermore discuss the possibility of gaining information about the behavior of the pion unpolarized transverse momentum dependent parton distribution from pion nucleus DY data.