Disney began implementing superhero media into their lexicon in the early 2010s, including the movies within the Marvel Cinematic Universe (MCU) and the show Lab Rats on the Disney XD channel. Disney’s goal in purchasing Marvel Comics and Marvel Studios was to create space for boys in their media offerings, which had traditionally been oriented towards girls. Lab Rats was Disney’s first journey into superhero media oriented towards boys from within their brand, specifically in the reliable genre of tween sitcoms. An analysis of this media observes the way that moral ambiguity is used to explore new Disney constructions of masculinity. Comparing and contrasting the way masculinity is portrayed in two movies from the MCU, Captain America: The Winter Soldier and Captain America: Civil War, with Lab Rats reveals Disney’s emerging ideal masculine traits for young and teenage boys. By implementing morally ambiguous characters in their superhero media, Disney shows young audiences that performing questionable acts for the greater good is not only socially acceptable but often glorified. The content from his era of Disney media reinforces the idea that “boys will be boys” by showing how bending the moral rules without consequences is a masculine trait. Conversely, Disney’s historic media offerings oriented towards young girls contain well-defined and strict moral messaging, which informs viewers that they need to be held to a higher standard of conduct than boys. The gendered dichotomy within this era of Disney media reinforces wider gender norms that have been perpetuated both in American society and in superhero media for decades. However, that content of the time is a product of the exploration when Disney was attempting to define the values of their masculine media. Lab Rats, Captain America: The Winter Soldier, and Captain America: Civil War serve as essential artifacts that preserve this moment of growth in Disney history.