During the past two decades, concerns about Black males’ academic achievement have been a major theme in the literature devoted to education and social sciences. Despite over two decades of studies focused specifically on Black males and their academic underachievement, the achievement gap persists. According to the National Center for Educational Statistic (2006), African-American males were reported as being disproportionally negatively represented in regards to academic achievement. Some researchers suggested Black children’s underachievement might be due to the lack of parental involvement. Other studies have highlighted statements of Black males who indicated parental involvement factors that contributed to their academic success. In Howard (2014) study, Black males stated their parents contributed to their success by “staying on them” regarding schoolwork and by setting higher expectations for their academic performance. The concept of parental involvement is cultural-bound and multi-dimensional. Parental involvement is also a bi-directional process that involves school and parents. The purpose of this study was to identify the factors that described parent involvement during high school of Black male students enrolled in a four-year college, and the distribution of perceived parent involvement during high school across this population. This study employed Yan and Lin’s (2005) parent involvement during high school survey to collect data from a convenient and purposeful sample of 146 Black males enrolled in an undergraduate degree seeking-program at a university in the southern region of the United States. The data was statistically analyzed using Confirmatory Factor analysis. The results of this study revealed the proposed hypothesized three factors model of parent involvement did not align well with the present data set. However, the individual subscale factors when analyzed in isolation, with some modifications, did align. As for the distribution of the factors, Family Norms were perceived as the most prevalent parent involvement subscale factor during high school for this particular population. Under the Family Norms factor subscale “Parent-teenager relationship” emerged as the most dominant variable, followed by “Educational expectations.” This study was significant as it highlighted and added to the knowledge relevant to successful Black males’ perceptions of parental involvement factors during their high school years. Identifying these factors can be useful toward improving graduation rates among Black males. In addition, information gathered can assist in further development of effective parent engagement school programming initiatives specific for this population.