12 Major Actors Who Auditioned For Clueless, Including Reese Witherspoon Being Up For Cher

When it comes to the best movies of the 1990s, Clueless is definitely up there! It’s not only a hilarious high school comedy with all its quotable lines and fashion moments, it’s a pop culture minefield of the era! While the original cast of Clueless is absolutely perfect, over the years, it's been revealed that numerous big name actors were almost in the classic ’90s movie. From Reese Witherspoon to Gwyneth Paltrow, a lot of massive stars crossed paths with the Beverly Hill-set film before Alicia Silverstone, Paul Rudd and more were officially cast.

Next time you watch Clueless, which is currently available to stream with a Paramount+ subscription, you can imagine how these other major actors would have been like as the main cast. Check them out:

Reese Witherspoon

Years before Reese Witherspoon starred in iconic movies like Legally Blonde, Election and Cruel Intentions, the actress auditioned “so hard” for Clueless, clearly to play Cher Horowitz. While talking to BuzzFeed, she shared the role that got away. It’s not hard to see her as the leading character, but of course she’s gone on to have a fabulous career without wearing that yellow plaid matching set. At the time, casting director Carrie Frazier recalls Witherspoon was “amazing,” but Alicia Silverstone was ultimately the right Cher.

Kerry Washington

At the same time Reese Witherspoon shared her audition for Clueless, her Little Fires Everywhere co-star Kerry Washington explained that she tried out for a role in the comedy as well! We can totally see Washington rocking the role of Cher’s best friend Dionne Davenport, but it was, of course, Stacey Dash’s part to win. While realizing their unique connection, Witherspoon and Washington joked they should “recreate” a Clueless scene together.

Ben Affleck

Another big name that could have been in the 1995 movie is Ben Affleck! At the time, Affleck was just stepping into the Hollywood scene with roles in School Ties and Dazed and Confused when he was considered for Paul Rudd’s part as Josh. Reportedly, Affleck passed on the role in order to do his first movie with Kevin Smith, Mallrats, as well as Glory Days. But as casting director Carrie Frazier said, per ET, she was “really trying to get” Affeck for the part and was “heartbroken” when it didn’t go to him at first.

Terrence Howard

Before Donald Faison earned the role of Murray in Clueless, Terrence Howard was reportedly a “top contender” for Dionne’s boyfriend. At the time, Howard was also pretty new to Hollywood, but he’d done guest spots in All My Children, Living Single and Family Matters. While Howard didn’t get the role, he would go on to be part of Mr. Holland’s Opus, which became a part of the 1995 award season conversation.

Zach Braff

Speaking of Donald Faison, the actor’s future BFF and Scrubs co-star Zach Braff was also up for Clueless as Josh as well. All we know is that he auditioned for Paul Rudd’s part, but didn’t get it. Braff and Rudd certainly look somewhat alike, and we have to wonder if Faison and Braff passed each other at the casting office years prior to meeting on Scrubs.

Angelina Jolie

Carrie Frazier has also revealed in the past that Angelina Jolie was among the actors who auditioned for Cher Horowitz at the time. However, the casting director shared that she felt Jolie was “too knowing” for playing the high schooler and found her to be “exactly the opposite” of what they needed for the role. 1995 would become the year Jolie first starred in a movie, but it was for Hackers instead.

Jeremy Renner

Another memorable member of the Clueless cast was Breckin Meyer’s Travis Birkenstock, who played the school’s resident stoner/skater kid. According to ABC, the eventual Avengers actor “came down to the finals” to play Travis at the time and was “very funny” in his audition. If he had gotten it, it would have been Renner’s first movie. Instead, 1995’s National Lampoon’s Senior Trip was his first film!

Keri Russell

Director Amy Heckerling reportedly had her “heart set” on Alicia Silverstone quite early on for Cher Horowitz (per ET), but she was asked to “explore” all the options, so she went ahead and did so. Among the names she has shared that auditioned is Keri Russell, who would of course go on to star in another iconic coming-of-age leading role with Felicity.

Sarah Michelle Gellar

Another future ‘90s TV icon who auditioned for Clueless just a couple of years before getting her big break leading a show was Sarah Michelle Gellar. The Buffy the Vampire Slayer actress auditioned as Cher’s nemesis at school Amber, which Elisa Donovan ended up playing. In this case, Gellar was actually offered the role before Donovan, but she had to pass it up due to a role she had at the time on All My Children.

Seth Green

Another actor that was reportedly up for Travis Birkenstock along with Jeremy Renner before Breckin Meyer, was the actor’s pal Seth Green. While he didn’t get the part, the actor would star in another iconic ‘90s teen movie in 1998’s Can’t Hardly Wait which starred the likes of Jennifer Love Hewitt.

Dave Chappelle

Dave Chappelle could have been in Clueless too in Donald Faison’s role of Murray. The director apparently met with the comedian while casting for the part after being a fan of Robin Hood: Men In Tights. However, what allowed Faison to win over him was his more “innocent” appeal. She felt Chappelle was a bit too edgy for the high school role.

Gwyneth Paltrow

Lastly, we also know that Gwyneth Paltrow was also in the running for Cher. It sounds like the studio really wanted her to be in the movie after she had been in 1993’s Flesh And Bone. However, the director shared she never actually got to see Paltrow audition. Paltrow would go on to star in Se7en that year!

So many huge actors were considered for Clueless. While it’s fun to imagine these other great talents as these iconic characters, the casting team of the comedy really made some incredible choices. We wouldn’t want it any other way!