Due to the innate unique highly reactive properties and short life-time, organic free radicals can often serve as promoters or inter-mediates to engage in various radical transformations, which are otherwise difficult to access by ionic pathway-based mechanisms. With the evolvement of radical chemistry, chiral radical catalyzed-transformations have recently emerged as an attractive and ro-bust platform for synthesis of chiral molecules of interest. Herein, we highlight several creative and strategic advances in chiral rad-ical catalyst design, cyclization reaction achievements, and future challenges.