Synthesis of buckybowls, especially, the large sized ones, have remained a huge challenge yet due to the inherent high strain induced by curvature. Herein, we report two novel bowl-shaped polycyclic aromatics with three chalcogen (sulfur or selenium) atoms and three methylene groups embedded at the bay regions of hexa-peri-hexabenzocoronene and an expeditious three-step synthetic strategy for these superbowls, including an aldol cyclotrimerization, a Scholl reaction, and a Stille reaction. The superbowls of this type feature a nanosized, compact, and C3vsymmetric architecture, composing of 19 fused rings, 48 constituent atoms. NMR spectroscopic and X-ray crystallographic studies confirmed their bowl-shaped geometries. The crystal structures revealed that they encompass 36 pyramidalized trigonal carbon atoms and have the bowl depths of 2.29 ˚A and 2.16 ˚A and diameters of 11.06 ˚A and 11.35 ˚A for the sulfur and selenium isologs. The curvature mainly distribute at the carbon atoms of the coronene frame and edge-to-convex packing predominates due to intermolecular C–H· · · π and chalcogen· · · π interactions in two instances. Variable temperature 1H NMR experiments and theoretical calculations demonstrated the bowls have considerably high inversion barriers. The optical and electrochemical properties were elucidated by UV/vis and fluorescence spectroscopy and cyclic voltammetry. Moreover, the aromaticity distribution and electrostatic potential characteristics as well as perpendicularly aligned convex-to-concave dipolemoments were investigated by density functional theory calculations.