28 Coming-of-Age Movies From the '90s That Are Sure to Get You in Your Feels

Directed by Ben Stiller (who also appears in the film), this dark comedy revolves around Lelaina (played by Winona Ryder), an aspiring videographer who decides to create a documentary about her and her friends after they graduate from college. Together, Lelaina and her three roommates share their struggles in life and love, and few movies capture the challenges faced by Gen-X youth like this one.