The cocrystals of a pharmaceutical model rac-ibuprofen with two pyridine-containing cocrystal formers were synthesized and their solid-state structures were carefully investigated in terms of crystal engineering and supramolecular chemistry. The target cocrystals were obtained by solvent-free grinding of rac-ibuprofen with the given cocrystal former and then suitable X-ray crystals were grown in acetonitrile solution and characterized by X-ray crystallography. Both structures adopted homo and hetero supramolecular synthons as well as other noncovalent interactions.