Clueless is one of my all-time favorite movies. It’s fun and bright, the music is great, the characters are lovable. It’s just great. I never get tired of watching it. While I’m not the original targeting demographic (mid-30s guy into sports and comics), the movie has always appealed beyond its targeted quadrant (younger women). Jen Chaney’s As If tells the story of how Clueless came to be and takes some educated guesses as to why the movie is so timeless and entertaining to so many of us. 
Chaney’s book is an oral history, which makes the read more enjoyable and informative. The reader gains not only an insider’s understanding of the movie, but also a glimpse at the personalities of everyone involved. Director Amy Heckerling (of Fast Times at Ridgemont High fame) had a strong vision and was able to surround herself with talented people who helped that vision come to life. The sense I got from reading the book is that Clueless happened because people believed in Heckerling and her vision. Her leadership inspired the best out of the cast and crew. The set, prop and clothing designers in particular stand out. I couldn’t believe that the movie was filmed in an unusually rainy winter.
The cast of Clueless all seemed to enjoy themselves during the filming process and look back on that time the way many of us would look back on a particularly fun summer camp or semester in college. I found Elise Donovan (Amber), Donald Faison (Murray), and Breckin Meyer (Travis) to be especially charming. Of course, Paul Rudd is charming as always. He and Brittany Murphy seemed to have been the cast and crew’s favorite people to work with.
Why does the movie remain popular across the generations? Some Jane Austen scholars believe that Clueless was true to the spirit of Austen’s timeless Emma, even more so that straight adaptations of the novel. That is what makes the movie stick the way Emma sticks. Despite the naivete and misguided actions of some of the characters, for the most part they’re trying to be good to one another. That’s a story we always want to see.
If you love Clueless, read the book!
(Side bar: Finding out who was up for certain roles is almost as entertaining as the movie itself. What would the Reese Witherspoon-centric version of the movie be like? Jeremy Renner as Travis the hippie skater? Ben Affleck as Josh? As if!)