Interest in the connection between masculinities and mental health continues to grow. However, no previous systematic review has explored this association for adolescents. We present the systematic review of 29 articles that explore the connection between adherence to stereotypical male gender role norms (e.g., emotional restriction), attributes (e.g., “ambitious”), and identity (most commonly, gender “typicality”) and internalizing behavior problems and social support. A total of 24,795 adolescent boys (6th‐12th grade) were included in the reviewed studies from 1997–2017. In the quantitative articles (n = 20), associations varied by aspect of masculinity assessed. Specifically, we found that greater endorsement of “masculine” traits (e.g., ambitious, assertive) was generally associated with fewer internalizing behavior problems and greater social support. However, lower gender “typicality” and higher adherence to stereotypical gender role norms were generally associated with more internalizing behavior problems and lower social support. In the qualitative articles (n = 9), the most predominant theme was emotional restriction (i.e., a gender role norm) and consequences for mental health. While research in this area is newer for community psychologists, the connection between masculinities and mental health is directly relevant to the field. Given the focus on individual‐level conceptions of masculinity and mental health found in our review, we describe key future directions for masculinities research in community psychology.