Organic macrocycles have been attracted much attention as functional host molecules that selectively recognize and encapsulate small molecules such as ions and organic molecules within its cavity. Usually, artificial organic macrocycles are synthesized by repetitive connection of monomer units and cyclization of linear oligomers formed thereby. In this context, there have been problems in the control of the number of units or in the selectivity of cyclic products over linear ones. This review focuses on recent breakthroughs that achieved the synthesis of novel functional macrocyclic molecules from fresh and original points of view to overcome the synthetic challenges.