The research examined the influence of outdoor advertising on politicians’ electoral success using the 2014 and 2018 Osun governorship election as a yardstick. It is of note that; the presence of various outdoor media platforms like billboard, poster, banner e.t.c has commanded a large number of followership for candidates. This research was anchored on Uses and Gratification Theory and Psychodynamic Theory. The research also used survey research method coupled with 250 copies of questionnaires that were administered to respondents within Ifelodun local government from which 220 copies were correctly filled and analyzed using frequency and percentage table method. Findings show that substantial numbers of the respondents (77.8%) who are main participants in the election; agreed that billboard is a veritable platform for political campaigns while they also admitted that outdoor advertising to an extent determines the choice of candidates in the voting process. The study, therefore, recommended that political billboards, posters, banners, and flyers should be strategically located and used in such a way that will not impede on the right of other contestants.