'Clueless' director Amy Heckerling explains how close Reese Witherspoon came to playing Cher

It’s tough to imagine Clueless, the iconic movie that hit cinemas on 19 July, 1995, with anyone else but Alicia Silverstone as the exceedingly privileged and sometimes oblivious, albeit big-hearted, Cher Horowitz.

Director Amy Heckerling tells Yahoo Entertainment that while Silverstone was the early favourite, she did at least consider others.

“I met with Reese Witherspoon, but she never read for it,” Heckerling says. “And by that time I was, like, already settled on Alicia, who I love. Who, you know, was in my head while I was writing.”

Heckerling says that she had a quick meeting over tea at a fancy Beverly Hills hotel with Witherspoon after being impressed with one of her performances, but Silverstone was “the girl in my brain.”

She has fond memories of other cast members, too, including the late Brittany Murphy, who played Cher’s friend Tai. The actress died in December 2009 at 32, and the Los Angeles County coroner said the cause was a combination of pneumonia, iron deficiency and “multiple drug intoxication.”

Read more: What the cast of Clueless did next

“Brittany breaks your heart. She was Tai. She was perfect,” Heckerling says. “She was a walking ball of sweetness and vulnerability and the energy. She was everything you could ever want.”

Heckerling, whose other work includes the equally iconic movie Fast Times at Ridgemont High, in 1982, recalls being impressed with Murphy’s delivery of a memorable line.

“When she did the ‘You’re a virgin who can’t drive,’ I just thought she killed it,” Heckerling raves. “You know, your blood runs cold. Like, somebody so sweet can turn into that. Oh my god. She was just amazing.”

The filmmaker confirms that she’s stayed on good terms with Stacey Dash, who portrayed Cher’s best friend Dionne, too. In the quarter-century since the film debuted to great fanfare on MTV and elsewhere, Dash has become a regular commentator on conservative politics.

“I love her, and I’ve tried to get her jobs on things and was told no because of that,” Heckerling says. “You know, I think she’s a wonderful actress, and I love her personally.”

Before she left, Heckerling also weighed in on the origins of the love story at the centre of Clueless — the one between Cher and Paul Rudd’s character Josh, whose mom was briefly married to Cher’s dad. “But you were hardly even married to his mother and that was five years ago,” Cher says in a scene where she’s complaining about having to see Josh at all anymore. (This is, of course, before she realises how she really feels.)

Well, it turns out, the situation came from Heckerling’s own life.

Read more: Clueless remake in development

“My grandparents were stepbrother and stepsister. And they met when they were teenagers,” she notes. “They fell in love, but they were always fighting and, you know, into their late 80s, they were still fighting with each other. I mean, like, cats and dogs fighting. So it never seemed strange to me.”

Watch the video above for the full interview.

— Video produced by Gisselle Bances