1. The movie is actually a modern retelling of Jane Austen's Emma.
2. Writer-director Amy Heckerling originally pitched Clueless as a Beverly Hills, 90210-style show for Fox called No Worries.
3. Another possible title for the show was Clueless in California, which was eventually shortened to just Clueless.
4. Fox wound up passing on the concept, scared it wouldn't be a hit. It eventually landed at Paramount.
5. Heckerling also directed '80s teen classic Fast Times at Ridgemont High.
6. Sarah Michelle Gellar was offered the role of Cher Horowitz, but had to pass due to scheduling conflicts with All My Children.
7. Reese Witherspoon was also considered for the role of Cher.
8. And Lauryn Hill and Terrence Howard auditioned for roles of Dionne and Murray.
9. Alicia Silverstone landed the role of Cher because Heckerling ultimately wanted the girl from "those Aerosmith videos."
10. Silverstone didn't formally audition for the movie — a lunch meeting sold Heckerling on the star.
11. Silverstone wasn't interested in the role at first, because she thought Cher was a "materialistic, annoying little bitch" with no redeeming qualities.
12. Paul Rudd (Josh) also didn't get the movie at first, and thought it was just another dumb teen comedy.
13. Still, he auditioned for every male role in the film, including Murray — Rudd didn't realize the character was meant to be black.
14. According to the casting director, Christian (Justin Walker) was the hardest part to cast, because actors didn't want to read for a gay character.
15. Stacey Dash (Dionne) was the oldest cast member outside of the adults at the time of filming. She was 27 with a 6-year-old son.
16. Brittany Murphy (Tai) was actually a virgin who couldn't drive when she uttered the line, "You're a virgin who can't drive."
17. Silverstone took inspiration from Marilyn Monroe and Lucille Ball to play Cher, but said she doesn't think that totally translated on screen.
18. Cher's mispronunciation of "Haitians" in the debate scene wasn't scripted. Silverstone really didn't know how to say the word, and Heckerling decided to leave the mistake in the movie.
19. Many of the terms in the movie — including "Betty" and "Baldwin" — were invented by Heckerling. The studio released a booklet of terminology called "How to Speak Cluelessly" to help promote the film.
20. And the cast had no idea what most of the invented slang meant when they first read the script.
21. Heckerling wasn't alone in coining Clueless-ology, though — Donald Faison (Murray) ad-libbed the phrase "keeping it real."
22. The high school in the film was named after Bronson Alcott, an early proponent of feminism and vegan diets, and father of Little Women author Louisa May Alcott.
23. Alicia Silverstone and Breckin Meyer (Travis Birkenstock) both actually attended the inspiration behind Bronson Alcott High, Beverly Hills High.
24. Heckerling audited classes at Beverly Hills High in order to make her script seem authentic.
25. Clueless was costume designer Mona May's first film. She went on to do the costumes for Romy & Michele's High School Reunion, The Wedding Singer, and Never Been Kissed.
26. There are reportedly 53 different kinds of plaid seen throughout the movie, with Cher wearing seven of them.
27. Cher has 60 costume changes throughout the movie.
28. The Chanel-inspired water bottle and cell phone cases designed for the movie got Karl Lagerfeld's approval, and even inspired Chanel to design its own versions.
29. Increased interest over the years prompted Calvin Klein to reissue Cher's white dress in 2010.
30. Paul Rudd wears a KU baseball cap in a few scenes, a nod to his alma mater, the University of Kansas.
31. The entire film was shot in just 40 days.
32. Cher's last name in the original script was Hamilton, a possible nod to Jennifer Jason Leigh's Fast Times at Ridgemont High character Stacy Hamilton. The name is seen on Cher's report card and on Mel's mail in the movie.
33. Cher's address — 901 Drury Lane Beverly Hills, 90210 — is a real address.
34. But the mansion seen in the film is actually located in — gasp — The Valley.
35. Heckerling saw people playing "Suck and Blow" at a party her friend threw while she was working on the movie, and decided to write it into the Val party scene.
36. Editors faked the clog hitting Tai in the head at the Val party in post-production. A special-effect clog had to be edited in, because the prop clog didn't look realistic enough.
37. Coolio is the one who suggested using "Rollin' With the Homies" in the movie.
38. Jeremy Sisto, who played Elton, made up the "Rollin' With the Homies" dance.
39. Though she's not in the film, Tara Reid was on set for the filming of the Val party.
40. Donald Faison only shaved the top of his head at the Val party; production asked him to keep hair on the sides of his head so he wouldn't look bald in previous scenes that still needed to be filmed. That's why Murray is almost always wearing a hat.
41. The freeway scene was inspired by Heckerling's own fear of driving on the freeway.
42. Twink Caplan, who played Mrs. Geist, was also a producer on the film.
43. Heckerling and Caplan are best friends in real life.
44. Heckerling makes a cameo in the final scene of the movie as Mrs. Geist's maid of honor.
45. Wallace Shawn, who played Mr. Hall, was actually a teacher before he became an actor.
46. The character Mr. Hall was based on Beverly Hills High's real debate and performing arts teacher, Herb Hall. He makes a cameo as the principal in the film.
47. An unexpected result of the film — some viewers were inspired to seek alcohol and drug treatment because Travis entered a 12-step program in the movie.
48. The Golden Girls cast spoofed the movie at the 1996 MTV Movie Awards.
49. Heckerling is working on a musical adaptation of Clueless — and Katy Perry has expressed interest in playing Cher.
50. And Silverstone recently said she's game for a sequel if Heckerling wants to write it.
