Say Anything Cast Then Now
You couldn't make "Say Anything" today. Lloyd Dobler would be standing outside Diane Court's house holding up his iPhone... nah, it just wouldn't work.

"Say Anything," which opened 25 years ago this week (on April 14, 1989), was definitely a movie of its time. In addition to that iconic moment where Lloyd uses his boombox to serenade Diane with Peter Gabriel's "In Your Eyes," it's the movie that made John Cusack into Generation X's favorite romantic leading man, as well as launching Cameron Crowe's directing career. And its countless cameos fill the film with faces that were familiar to audiences a quarter-century ago (blink and you'll miss Chynna Phillips, of Wilson Phillips fame, as Joe's new girlfriend) -- or those that were about to be, like future Pearl Jam guitarist Stone Gossard (he plays a cab driver), Dan Castellaneta (on the eve of fame as the voice of Homer Simpson, he plays Diane's teacher), and 1990s kickboxing legend/action star Don "The Dragon" Wilson (as Lloyd's sparring partner).

Whether they had leading roles or cameos, many of the film's actors went on to flourish in the 1990s before traveling on more unpredictable paths in recent years. Here's what became of the "Say Anything" crew, and here's how, like Lloyd, they handled their own dare-to-be-great situations.

Article photo courtesy Fox