Editing Clueless (section)

===Casting===
Heckerling first saw [[Alicia Silverstone]] in the [[Aerosmith]] music video for "[[Cryin']]" and kept her in the back of her mind for the role of Cher.<ref name="vanityfair.com" /> When the film was still in development at Fox, executives suggested [[Alicia Witt]], [[Keri Russell]], [[Tiffani Thiessen]], [[Gwyneth Paltrow]], and [[Angelina Jolie]] for the part.<ref name="vanityfair.com" /> Heckerling met with [[Reese Witherspoon]], who already had a few film roles to her credit.<ref name="vanityfair.com" /> Though Silverstone only had the thriller ''[[The Crush (1993 film)|The Crush]]'' as her previous film, the studio did not pressure Heckerling to cast big stars, and Silverstone ultimately won the role of Cher.<ref name="mentalfloss.com" /> [[Ben Affleck]] and [[Zach Braff]] auditioned for the role of Josh.<ref name="vanityfair.com" /> [[Sarah Michelle Gellar]] was offered the role of Amber Mariens but turned it down due to her commitments to ''[[All My Children]]'', while [[Zooey Deschanel]] auditioned for the role of Amber as well.<ref>{{cite magazine |last=Jones |first=Eleanor |url=https://www.cosmopolitan.com/uk/entertainment/a33973/clueless-film-trivia-facts/ |title=14 things you never knew about Clueless |magazine=[[Cosmopolitan (magazine)|Cosmopolitan]] |location=UK |date=March 6, 2015 |access-date=November 23, 2022}}</ref> [[Lauryn Hill]] auditioned for the role of Dionne, which eventually went to Stacey Dash.<ref>{{cite web | url=https://time.com/3944547/clueless-20th-anniversary/ | title=20 Things You Never Knew About 'Clueless' | date=July 6, 2015 }}</ref>

[[Seth Green]] auditioned for the role of Travis and [[Alanna Ubach]] was considered for the role of Tai.<ref name="vanityfair.com" /> [[Terrence Howard]] and [[Dave Chappelle]] were considered for the role of Murray.<ref name="vanityfair.com">{{Cite magazine |last=Chaney |first=Jen |date=June 9, 2015 |title=The Definitive Oral History of How Clueless Became an Iconic 90s Classic |url=https://www.vanityfair.com/hollywood/2015/06/clueless-oral-history-20-anniversary |access-date=March 26, 2022 |magazine=[[Vanity Fair (magazine)|Vanity Fair]]}}</ref> [[Jeremy Renner]] and [[Jamie Walters]] auditioned for the role of Christian, and [[Jerry Orbach]] and [[Harvey Keitel]] were considered for the role of Cher's father, Melvin Horowitz.<ref name="vanityfair.com" /><ref>{{cite news|url=https://www.huffpost.com/entry/clueless-trivia_n_7208320?ir=Entertainment|title=5 Things You Didn't Know About 'Clueless,' According To The Casting Director|last=Van Lulind|first=Todd|access-date=June 4, 2022|date=May 7, 2015|website=[[HuffPost]]}}</ref>

The character of Wendell Hall, played by [[Wallace Shawn]], was inspired by a real-life debate teacher at Beverly Hills High School and a friend of Heckerling's. Prior to full-time acting, Shawn had been a teacher and drew on his experience for his portrayal of Mr. Hall.<ref name="mentalfloss.com" />