This study investigates the interplay between particle shape, grading and initial sample density, three of the most important factors influencing the mechanical behaviour of sheared granular assemblies. Using the discrete element method (DEM), two-dimensional assemblies of varying initial sample density, particle aspect ratio, (AR), and coefficients of uniformity, ({C}_{u}), were prepared and subjected to drained biaxial shearing until the critical state was reached. We assessed the interplay between each of these parameters by evaluating whether the effect of any given parameter on a mechanical quantity is influenced by any other parameter. Our analyses show that the effect of some of these key parameters on mechanical response, can indeed be influenced by other key parameters. The effect of the particle (AR) on the peak shear strength for the initially dense assemblies differs when compared with the medium-dense assemblies. The mechanical coordination number of the assemblies at the initial state correlates with the peak strength thereby explaining the interplay between particle (AR) and initial sample density on the peak shear strength. The linear relationship established between strength and dilatancy for a combination of all assemblies studied suggests that the strength-dilatancy relationship is a unique characteristic of granular assemblies. The dilatancy of the assemblies correlates strongly with the amount of contacts lost during shearing. The interplays found between particle shape, grading and initial sample density in this study show that to develop robust constitutive models for the prediction of granular material behaviour, the effects of multiple factors must be considered.