“I want­ed it to feel like enter­ing a world that makes you hap­py” – Amy Heck­er­ling on Clue­less at 25

“There’s a lot of movies that feel like they’ve nev­er gone away, and for me Clue­less nev­er has,” smiles Amy Heck­er­ling, recall­ing her 1995 teen com­e­dy. ​“I always wind up in Clue­less-land play­ing with these char­ac­ters, their lan­guage and that time peri­od – it’s a big escape for me.”

In the years since it was released Clue­less has spawned a book series, a three-sea­son TV show and a glitzy broad­way pro­duc­tion, but it’s Heckerling’s orig­i­nal pop-cul­ture com­e­dy, star­ring Ali­cia Sil­ver­stone as the eter­nal­ly opti­mistic and obscene­ly wealthy high school socialite Cher, that has become icon­ic. Today, the film stands as an unlike­ly paragon of diverse cast­ing and gen­der equal­i­ty (along­side being infi­nite­ly quotable and fun), yet back before pro­duc­tion start­ed the direc­tor admits she strug­gled to artic­u­late her vision.

“I first wrote it as a TV pilot for Fox, but they didn’t make it,” she recalls. Thir­teen years ear­li­er, Heck­er­ling had revi­talised the teen genre with the Cameron Crowe-penned Fast Times at Ridge­mont High. With Clue­less, she returned to famil­iar ground; inspired by Jane Austen’s lit­er­ary clas­sic ​‘Emma’ and fol­low­ing plucky over­achiev­er Cher as she plays match­mak­er to new BFF Tai (Brit­tany Mur­phy) in the cor­ri­dors of her Bev­er­ly Hills high school.

“I had the char­ac­ter real­ly strong­ly imag­ined in my head and I was try­ing to think of a fresh plot that would go along with this kind of girl – some­body who’s just amaz­ing­ly pos­i­tive,” Heck­er­ling says. ​“I remem­ber read­ing ​‘Emma’ in col­lege and thought every­thing in it was so applic­a­ble to the things that’d work for a teenage girl. It was time­less and I was off and running.”

How­ev­er, when Heck­er­ling sub­mit­ted her first script – then still a TV pilot – the studio’s notes didn’t exact­ly gel with her idea of Cher’s world. ​“The thought was that mak­ing a movie just for girls would lim­it your audi­ence, and they want­ed some­thing that would appeal to boys,” she reveals. ​“There was a lot of think­ing in Hol­ly­wood that was a bit old-fash­ioned and less about peo­ple of colour, women and gen­der. They want­ed to see young boys which they thought were the major audience.”

There was also anoth­er big change that Heck­er­ling strug­gled to get on board with. ​“They want­ed to see scenes with the boys that didn’t include Cher. It was a first-per­son nar­ra­tive and we need­ed to hear what Cher was think­ing – this was some­thing that was com­ing out of her head. It just didn’t make sense.”

Thank­ful­ly, pro­duc­er Scott Rudin inter­vened, tak­ing Heckerling’s treat­ment from Fox to Para­mount and repo­si­tion­ing it as a fea­ture film. ​“It was get­ting turned into some­thing that felt out-dat­ed. It was a dif­fer­ent ani­mal and not what I had writ­ing. Thank god it went to Para­mount and Scott. All his notes were per­fect­ly in-sync with what I want­ed to do with it.”

Not long after, Heck­er­ling began the cast­ing process, with the young star of Aerosmith’s lat­est batch of music videos catch­ing her eye as a poten­tial lead­ing lady. ​“I was watch­ing the Cryin’ video on my tread­mill and ran off to find a VHS so I could tape her to show peo­ple and say this is who I want,” Heck­er­ling laughs, remem­ber­ing the first time she saw Sil­ver­stone. ​“You see Ali­cia and just care about her. There’s some­thing so child­like and vul­ner­a­ble and her sweet­ness comes through. You imme­di­ate­ly smile.”

Cast oppo­site Sil­ver­stone was a young Paul Rudd as Josh, Cher’s snarky ex-step broth­er who is intern­ing for her hot-shot lawyer dad (Dan Hedaya) and unafraid of point­ing out her some­times super­fi­cial atti­tudes on life. ​“He’s fun­ny, smart and a won­der­ful actor,” says Heck­er­ling of Rudd. ​“You could see him giv­ing her shit but still being warm heart­ed. There wouldn’t be any obnox­ious, phoney ban­ter­ing between the two – there would be some harm to it.”

Inter­est­ing­ly, Rudd wasn’t the director’s first choice – she ini­tial­ly envi­sioned Beast­ie Boy Adam Horovitz (aka Ad-Rock) as Cher’s would-be love inter­est. ​“I have a board where my scenes are laid out and I put lit­tle pic­tures of peo­ple who are in my mind as char­ac­ters are start­ing to devel­op,” she explains. ​“Adam was the char­ac­ter in my brain when I was writ­ing Josh but he nev­er came into cast­ing. He was busy with hit albums and being on tour.”

Anoth­er well-known star who almost crossed paths with Cher was come­di­an Dave Chap­pelle in a role that ulti­mate­ly went to future Scrubs star Don­ald Fai­son. ​“I’d seen Robin Hood: Men in Tights and direc­tor Mel Brooks was crazy about Dave and real­ly want­ed me to meet him,” says Heck­er­ling on cast­ing the role of pop­u­lar high school­er Murray.

While impressed with Chappelle’s style, he sim­ply wasn’t the right fit for Cher’s glossy clique. ​“As I was writ­ing, it was appar­ent that I need­ed some­body that would be real­ly imma­ture and a pup­py. Some­one that – if they were act­ing like a tough guy – wouldn’t seem tough at all,” rea­sons Heck­er­ling. ​“Dave was so smart and edgy but just not the right flavour for Murray’s goofy, child­like character.”

With cam­eras rolling, Heck­er­ling and her young cast had fun splic­ing the roman­tic sophis­ti­ca­tion of ​‘Emma’ with the slang-heavy vocab­u­lary of Los Ange­les teens. ​“One thing that was a lot of fun was hav­ing the bones of a plot that was so bril­liant and fig­ur­ing out how to find an equiv­a­lent with­in the high school world,” she says of com­bin­ing these two very dif­fer­ent aesthetics.

Plus, as a New York native, Heck­er­ling was at an added remove from the scene she was try­ing to cap­ture: ​“I’d fig­ure out what every­body was try­ing to say and how I would say it in my New York-ese, then trans­late that into a Cal­i­forn­ian lan­guage that wasn’t exact but felt fun for them to say.” Of course, there was log­ic behind Cher’s lan­guage: ​“I tried to make every­body have cer­tain slang but also wide vocab­u­lar­ies. These peo­ple were well-edu­cat­ed so when they used slang, it’s because they chose to – but they could also be very well spo­ken. I want­ed that combination.”

Craft­ing Heckerling’s vibrant, sun-soaked world was cin­e­matog­ra­ph­er Bill Pope, who had a unique under­stand­ing of just how impor­tant pep­py and pos­i­tive light­ing was for the direc­tor. ​“Bill real­ly taught me a lot. I have a lot of issues about things that make me depressed visu­al­ly,” says Heck­er­ling, can­did­ly recall­ing a child­hood spent in a dim­ly-lit Bronx apart­ment con­trolled by her ener­gy-wary father. ​“A lot of cin­e­matog­ra­phers love that Rembrandt‑y look, but I need things to have some sparkle and glitter.”

Thanks to Pope’s tonal tweaks, Clue­less remains one of the most joy­ous visu­al expe­ri­ences of ​’90s cin­e­ma. ​“He under­stood my emo­tion­al con­cerns and what I want­ed the movie to feel like – like you’d entered a world that would make you happy.”

A quar­ter of a cen­tu­ry lat­er and audi­ences who grew up on the zeit­geist-cap­tur­ing Clue­less have start­ed mak­ing them­selves known – some in pret­ty big ways. ​“Olivia Wilde, who made Books­mart, told me she grew up watch­ing Fast Times and Clue­less and I was very hon­oured because her movie was won­der­ful,” says Heck­er­ling warm­ly. ​“That she was acknowl­edg­ing these movies made me feel very proud.”

While Heck­er­ling may shy away from plac­ing any per­son­al sig­nif­i­cance on the cul­tur­al impor­tance of her work (“I don’t think like that,” she says), Clue­less remains a time in her life where the stars aligned to cre­ate some­thing endur­ing. ​“I’ve made a few movies and you’re always com­pro­mis­ing. There’s always things you had in your head that nev­er came out exact­ly as you want­ed – but with Clue­less, every­thing came out the way I want­ed. That just doesn’t hap­pen in life.”