It stars Alicia Silverstone with supporting roles by Stacey Dash, Brittany Murphy, and Paul Rudd (in his film debut).

Heckerling studied Beverly Hills High School students to understand how teenagers in the 1990s talked and learned some appropriate slang terms from them.

Dionne has a long-term relationship with popular student Murray Duvall, though Cher believes she should be dating more mature men.

Josh Lucas, the socially conscious son of Mel's ex-wife of only a few weeks, visits Cher and her father during a break from college.

After receiving a poor grade, Cher decides to orchestrate a romance between two teachers at her school, Miss Geist and the hard-grading Mr. Hall.

When a "clueless" transfer student named Tai Frasier arrives at the school, Cher decides to make her her next project.

Cher tries to extinguish the attraction between her and Travis Birkenstock, an amiable but clumsy skateboarding slacker, and instead steers Tai towards handsome, popular student Elton Tiscia.

Despite the failure of her romantic overtures, Cher remains friends with Christian due to her admiration of his taste in art and fashion.

Cher's privileged life takes a negative turn when Tai's newfound popularity strains their relationship and when she fails her driving test and, for the first time, cannot change the result.

Sometime later, Mr. Hall and Miss Geist get married, and Cher attends the wedding with Josh, Dionne, Murray, and Tai and Travis (who have begun dating).

"[10] Heckerling, having read the Jane Austen novel Emma in college and loving the title character's positivity, decided to write the script around an Emma-like character, saying, "I started to think, 'What's the larger context for that kind of a 'nothing can go wrong' 'always looks through rose colored glasses' kind of girl?

As research for the script, Heckerling sat in on classes at Beverly Hills High School to get a feel for the student culture,[12] commenting, "...one thing I observed was these girls in a constant state of grooming.

[11] Twink Caplan, Heckerling's friend who had worked with her on past projects, said film executives at Fox were wary of the story being too female-oriented to appeal to a large enough audience.

[9][10] Rudin's support led to increased interest in the script, and it became the subject of a bidding war between studios which was eventually won by Paramount Pictures.

[9] Heckerling was excited, as Paramount owned several major youth-centered television channels, such as MTV and Nickelodeon, which were suited to the film's target demographic.

[11] 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.

[11][14] 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.

[17] Scenes depicting the fictional Bronson Alcott High School campus including the tennis courts, outdoor cafeteria, and the quad were filmed at Occidental College in Los Angeles.

[19] Other notable filming locations include the former Westside Pavilion shopping mall, Circus Liquor in North Hollywood, where Cher is mugged in her designer dress, and Rodeo Drive, featured in Cher's "crisis" scene as she dejectedly wanders around after a failed driver's test and a confrontation with Tai.

The iconic plaid set worn by Cher Horowitz in the film was "a nod to a Catholic schoolgirl uniform, but taken to another level and, turned designer.

[3] The box office success brought the then-largely unknown Silverstone to international attention and earned her a $10 million, multi-picture deal with Columbia TriStar.

The website's critics consensus reads, "A funny and clever reshaping of Emma, Clueless offers a soft satire that pokes as much fun at teen films as it does at the Beverly Hills glitterati.

"[49] Heckerling later described Silverstone as having "that Marilyn Monroe thing" as a "pretty, sweet blonde who, in spite of being the American ideal, people still really like.

Cher's verbal style is also marked by ironic contrasts between current slang and historical references, such as when she compares Tai to "those Botticelli chicks".

[53][54] Fashion as a form of self-expression played an important role in the narrative and character development of the film, television series, and novels, which are topics examined by academic Alice Leppert.

[56] Clueless was the main inspiration for Australian rapper Iggy Azalea's music video for her 2014 song "Fancy" featuring Charli XCX.

[59] A June 2018 episode of Lip Sync Battle featured Silverstone miming to "Fancy", wearing Cher's yellow plaid skirt suit.

[61][62] In the second episode of the second season of the BBC America thriller series Killing Eve, "Nice and Neat" (2019), the Russian assassin Villanelle calls her agency and uses the codename Cher Horowitz to secretly inform her boss she is in trouble and needs to be rescued after being kidnapped.

[63] A 2020 Discover Card commercial featured a clip from the film consisting of Cher Horowitz saying her famous phrase "Uh!

[74] The CD-ROM is intended for girls age 8 and up, and includes a soundtrack, trivia, makeover and dress-up activities, and six video games.