Organic molecular crystals contain long-range dispersion interactions that can be challenging for solid-state methods such as density functional theory (DFT) to capture, and in some industrial sectors are overlooked in favor of classical methods to calculate atomistic properties. Hence, this publication addresses the critical question of whether dispersion corrected DFT calculations for organic crystals can reproduce the structural and energetic trends seen from experiment, i.e., whether the calculations can now be said to be truly "on-trend." In this work, we assess the performance of three of the latest dispersion-corrected DFT methods, in calculating the long-range, dispersion energy: the pairwise methods of D3(0) and D3(BJ) and the many-body dispersion method, MBD@rsSCS. We calculate the energetics and optimized structures of two homologous series of organic molecular crystals, namely, carboxylic acids and amino acids. We also use a classical force field method (using COMPASS II) and compare all results to experimental data where possible. The mean absolute error in lattice energies is 9.59 and 343.85 kJ/mol (COMPASS II), 10.17 and 16.23 kJ/mol (MBD@rsSCS), 10.57 and 18.76 kJ/mol [D3(0)], and 8.52 and 14.66 kJ/mol [D3(BJ)] for the carboxylic acids and amino acids, respectively. MBD@rsSCS produces structural and energetic trends that most closely match experimental trends, performing the most consistently across the two series and competing favorably with COMPASS II.