14 Actors Who Almost Starred in ‘Clueless’ (Including Several ’90s Darlings!)

The 1995 coming-of-age comedy *Clueless*, a modern take on Jane Austen’s *Emma*, is a pop culture staple. Few realize that the iconic cast we adore wasn’t the only talent considered for the film. This look back reveals a fascinating world of “almosts” and “what-ifs” within the industry, and a lot has changed since.

The Alternate Universe of *Clueless*: Casting Choices and Beyond

The success of *Clueless* ignited the careers of Alicia Silverstone, Paul Rudd, and Stacey Dash, to name a few. However, the casting process was a journey filled with numerous auditions and potential stars. This article dives into the fascinating “almost-cast” list.

Cher Horowitz: The One That Got Away (For Some)

Reese Witherspoon, now a household name, auditioned for Cher. Director Amy Heckerling saw potential but ultimately felt Alicia Silverstone embodied the role’s essence. Witherspoon’s career blossomed with *Legally Blonde*, *Sweet Home Alabama* and *Walk the Line*, demonstrating her versatility. This highlights how casting can be a matter of fit.

Angelina Jolie: A Different Kind of Knowing

Angelina Jolie was also considered for Cher. However, casting director Carrie Frazier noted that Jolie’s persona was too “knowing” for the character. Jolie’s career skyrocketed, with roles in *Lara Croft: Tomb Raider*, *Mr. & Mrs. Smith*, and *Girl, Interrupted*, for which she won an Oscar.

Other Cher Contenders

Gwyneth Paltrow and Keri Russell were also discussed for the role of Cher. Paltrow’s performance in *Seven* later that year brought her a lot of recognition, and Russell gained acclaim on *Felicity*.

Other Notable Mentions: Tiffani Thiessen, Alicia Witt

Tiffani Thiessen, known for *Saved by the Bell* and *Beverly Hills, 90210*, and Alicia Witt, already a recognized child actress from *Dune*, were also considered for Cher. These names emphasize the breadth of talent considered for the role.

Beyond Cher: The Supporting Players and the Casting Carousel

Amber Mariens: The Role Sarah Michelle Gellar Almost Played

Elisa Donovan ultimately played Amber Mariens, Cher’s rival. However, Sarah Michelle Gellar was the original choice. She couldn’t take the role due to her commitment to *All My Children*. Gellar’s career soared with *Buffy the Vampire Slayer*, showcasing her versatility.

Josh Lucas: The Heartthrob

Paul Rudd’s portrayal of Josh is iconic, but he wasn’t the only one considered. Ben Affleck was also in the running.

Ben Affleck: A Nearly “Clueless” Heartthrob

Ben Affleck was seriously considered for Josh. Frazier was “heartbroken” he didn’t get the part. Affleck’s success in *Good Will Hunting*, which won him an Academy Award, and roles in *Armageddon* and *Pearl Harbor* cemented his place in Hollywood.

Zach Braff: The Almost-Josh

Zach Braff, known for *Scrubs*, also auditioned for Josh. Braff’s chemistry with Silverstone was less impactful, leading to Paul Rudd’s casting.

Murray Duvall: The Many Faces of a Sidekick

Donald Faison played Murray Duvall, but the casting process was competitive. Dave Chappelle was considered.

Dave Chappelle: A Different Kind of Comedy

Heckerling met with Dave Chappelle, but his “cynical, grown-up, funny” persona didn’t quite fit the role. Chappelle’s career soared, co-creating *Chappelle’s Show*, and starring in *The Nutty Professor*.

Terrence Howard: A Close Contender

Terrence Howard also auditioned for Murray, even reading with Stacey Dash. Faison and Howard had been friends, but were competing for the same role. Howard went on to star in *Hustle & Flow*, earning an Academy Award nomination.

Travis Birkenstock: The Skater Boy

Breckin Meyer brought the character of Travis to life. Jeremy Renner was also a contender for the role.

Jeremy Renner: The Action Hero’s Early Days

Jeremy Renner, now known for action roles, was considered for Travis. Renner’s career took off, with *The Hurt Locker* earning him an Oscar nomination.

Seth Green: Best Friends Competing

Seth Green was another contender for Travis. Green’s success includes *Idle Hands* and the *Austin Powers* films.

The choice came down to Meyer and Green, who were best friends at the time. Green’s then-girlfriend, Alanna Ubach, was considered to play Tai, as well.

Other Stars Who Almost Made It

Kerry Washington: Bonding Over Rejection

Kerry Washington also auditioned for a role in *Clueless*, but didn’t specify which one. She and Reese Witherspoon shared a laugh over missing out on a part in the hit film. Washington’s success includes *Scandal*.

The “almost-cast” list for *Clueless* illustrates the unpredictable nature of Hollywood. While some actors weren’t the right fit for this particular film, they went on to achieve remarkable success.

Casting directors consider countless factors. The director’s vision, chemistry between actors, and actors’ availability all contribute to these important decisions. The process is a blend of art and logistics.

Did you know? The casting process can change a film’s trajectory. Different actors could have brought entirely different interpretations to these characters.

Pro tip: Want to learn more about casting? Explore behind-the-scenes documentaries on your favorite films.

Are there any other films where you were surprised by the “almost-cast” list? Share your thoughts in the comments below! If you enjoyed this article, check out some of our other articles on the best movies of all time.