Rigid hydrocarbon macrocycles with radially-oriented π-systems and continuous conjugation have attracted great interest in recent years. These molecular belts have novel optoelectronic properties and host-guest behavior. Certain belts may also ultimately lead to a rational synthesis of carbon nanotubes. The high strain associated with the nonplanar, conjugated backbones requires the development of new synthetic methods, and clever synthetic design. Herein we describe the synthetic history and properties of these structurally simple but synthetically challenging molecules.