Winona Ryder leads a cast of Generation X-ers in Stiller’s era-defining debut, a tender romantic comedy and a self-aware portrait of youthful aimlessness in the pop-culture-saturated 1990s. Helen Childress’ rich screenplay afforded Ryder her sharpest present-day dialogue since Heathers in the plum role of a college valedictorian whose documentary filmmaking career is entwined with the travails of her friends.