The gender gap in education has been widening over the years as girls push ahead, and boys lag behind. Various factors are considered when attempting to explain this trend as well as how it can be addressed. This study focuses on the role of media, specifically children’s TV shows, how they portray masculinity and how those portrayals may shape boys’ identities and behaviour in school. A content analysis of six boys’ television shows has been conducted to document some of these messages. With the exception of one show, overall findings illustrate that the television shows included in this study do not represent a range of masculinities, providing limited messages to young viewers. This study does not assess the direct relationship between these messages and behaviour in the classroom but considers one possible explanation for the gender gap, and makes suggestions aimed at transforming practices in the classroom. Even with research suggesting the need for exposure to different types of masculinities, such issues cannot be addressed until society believes that young boys need encouragement and support in forming their own individual gender identities. Keywords: boys; education; gender; gender gap; masculinity; television.