Youth is a considerable part of Brazilian society and the production of research in this field is growing, highlighting the challenge of understanding the diversity of youth cultures. This research aims at the interpretation of the life trajectories of five young people of the popular class, residents of the metropolitan region of Rio de Janeiro, who participated in the documentary film Últimas Conversas, by Brazilian director Eduardo Coutinho. When narrating their life stories in two different moments in the film, and in this research, young people address social factors that interfere in their experiences. Gender, socioeconomic background, place of residence and skin color appear intertwined with your family and school life and your experiences in the world of work. Although they are of similar social origin, you can see the diversity of their behaviors, choices and values. From the five trajectories of the young people interviewed, it is possible to identify and understand the different ways of facing persistent social inequalities. This longitudinal research is in the field of sociological studies on youths of the popular class, considering the limitations imposed by inequalities and using cultural factors to reflect on the existing variations in the trajectories of these young people and understand what allows access to different paths and opportunities.