In the context of Harold Lloyd’s early career, The Freshman (1925) drew upon Lloyd’s use of parody and slapstick comedy to redefine ‘“regular’” American masculinity in the 1920s as youthful, white, heterosexual, and middle class. Through genre and star discourse from a wealth of primary sources, including early Lloyd comedy shorts that have not previously received significant attention, this chapter argues for American masculinity in Lloyd’s silent films as a liminal position between working and leisure class, active and passive, child and adult, reality and fantasy. From his early shorts as the Chaplinesque Willie Work and Lonesome Luke to the development of his famous Glass character, Lloyd explored American middle-class masculinity as a liminal form of social mobility predicated on playfulness and performance, blurring lines between participant and spectator in ways that would inform The Freshman.