Long-lived triplet bisarylmethylenes are now well-known. Experimental data (primarily ESR hyperfine parameters) suggest that the carbon framework of long-lived bisarylmethylenes approaches D-2d symmetry, as ortho-substitution forces the central angle to approach 180degrees. According to DFT modeling, the approach of the central angle to 180degrees is accompanied by a dramatic shortening of the central CC bonds and severe quinoid distortion of the phenyl rings. In contrast, X-ray investigation of bis(2,4,6-trichlorophenyl)methylene shows a structure closer to the carbene valence bond representation with less seriously distorted phenyl rings, a more acute central angle, and a longer bond from the methylene carbon to the aryl substituent. We address the difficulty of achieving a balance of cumulene and carbene character, treating the model systems diethynylmethylene, dicyanomethylene, and diisocyanomethylene by post-Hartree-Fock methods CAS and CCSD as well as DFT models, and applying the perturbation-corrected CAS methods to the chloro and methyl ortho-substituted bisphenyl carbenes.