In this work, we have developed a method that can determine how the helical twist of ⇡-MOs evolve through any given molecule. This method can be used to quantify the deviation of the MO from a perfect cylindrical helix and thus allows us to probe the helicality of MOs for a diverse set of molecules. We find a pronounced difference in the change in helical curvature of the ⇡-MOs of different types of linear systems. Notably, the MOs of polyynes do not achieve the same level of helicality as equivalent-length cumulenes. The distribution of helical twist of the MOs depends on the chemical nature of the ⇡-system. This change in uniformity of the twist is not tied to the difference between polyynic and cumulenic systems as the staircase-like features, and this change in helicality, are also present in the investigated metallacumulene, trans-[EtC=(C=) 4 C=Ru=(C=) 4 CMe] 2+ . The degree of helicality is very sensitive to some types of structural changes while being almost invariant to other types. For example, twisting the end-groups of polyynes and cumulenes has a considerable effect on the helicality of their MOs. Contrarily, the bent bond angles in cycloallenes has negligible effect on the helicality of their HOMO. Our method allows for a straightforward and systematic analysis of a range of molecular systems independent of how each system is partitioned.