Going to extremes: Deformed molecules with “planar” carbon atoms, orthogonal double bonds, nonlinear triple bonds, and aromatic rings distorted into a boat structure have interested chemists for decades. This essay traces the reasons for this fascination, and finds them in the psyche of the researcher: the wish to transgress the limits of normalcy, the insatiable curiosity to extend the limits of method and mind, and the eternal human joy to find something new while playing.