Ben Stiller’s directorial debut is an irreverent look at the harsh realities of life after college that captures the misadventures of Lelaina (Winona Ryder), an aspiring TV production assistant, and her relationships with her sarcastic roommate, Vickie (Janeane Garofalo), friends Sammy (Steve Zahn) and Troy (Ethan Hawke) and an ambitious video executive, Michael (Stiller). A comedic and cultural touchstone, Reality Bites encapsulated the ennui and existential crises of Generation X like no other.