Celebrity endorsement (CE) has been successful as one of the Marketing Communications tools and has attained such popularity but abound extant literature and various research works have not consider challenges Corporate Organizations are confronted with in their business endeavor by engaging Celebrities to endorse the organization’s brands. It is believed that in every endeavor there are few challenges that are set to militate against whatever good intentions or objectives that venture might have. This paper therefore, focus is on findings from a research project that reflected upon the challenges of Celebrity endorsement (CE) and how they have affected diffusion. CE was applied to capture Customers and Business Executives experiences on using Celebrity Endorsers which provided a basis for observation and reflection. The research adopted both quantitative and qualitative methodology. Questionnaires were used to collect the data. The study surveyed 30 Business Executives. The outcome of the study has proved that despite the enormous feat chalked by CE successes and its popularity attained factors such as Management, Publicity, Contract, Customer match-up and Competition were identified to be the challenging factors that have been drawbacks inhibiting Celebrity endorsements.