It's been 20 years since Amy Heckerling's Clueless (1995) first released but the film still resonates with the audience that initially saw it and anyone who might see it again today (ie. Iggy Azalea's homage to the film in her video for Fancy). Based on Jane Austen's classic novel Emma (1815) about a meddlesome young girl with a heart of gold, Clueless transported the iconic material to a Beverly Hills high school. Featuring Alicia Silverstone in her first leading role, the film also starred Paul Rudd (Hey, there Ant-Man), Donald Faison, Jeremy Sisto, Stacey Dash and the late Brittany Murphy (Girl, Interrupted). Clueless made them all breakout stars that summer of 1995.
The film's teen terminology became instantly quotable, every girl wanted Cher's wardrobe and the soundtrack perfectly reflected was what was popular in the 90s - from Beastie Boys, Radiohead, Coolio, Counting Crows to The Muffs. Based on small budget of $12-13 million, Clueless grossed around $56 million domestically and opened No. 1 at the box office. Not bad for a film that was initially pitched as a television show. The success of the film lead to a spinoff TV series which launched on ABC and finished out the next two seasons on UPN. Most of the cast with the notable exceptions of rising stars Alicia Silverstone and Paul Rudd reprised their roles in the series.
As If!: The Oral History of Clueless by Jen Chaney. There you'll find notable nuggets of information on casting (Reese Witherspoon and Angelina Jolie were considered for the role of Cher, Ben Affleck read for the part of Josh which eventually went to Paul Rudd), how Heckerling came up with Cher and Dionne's lingo and how hard the everyone worked behind the scenes to make this little film a reality.