Summary

Reese Witherspoonhas had various memorable roles on the big screen, among them Elle Woods inLegally Blonde, but she almost played another iconic rom-com blonde six years earlier. Witherspoon’s acting career began in 1991 with the TV filmWildflowerand the coming-of-age movieThe Man in the Moon, but her big break arrived with the 1998 teen fantasy comedy-dramaPleasantville. Witherspoon’s next big role was Annette Hargrove in the teen dramaCruel Intentionsthe following year, along with Tracy Flick in the black comedyElection.

Witherspoon became one of the most beloved rom-com and teen comedy actresses in 2001 when she starred inLegally Blonde. Directed by Robert Luketic and based on the 2001 novel of the same name by Amanda Brown,Legally Blondefollows Elle Woods, a sorority girl who, in an attempt to win her ex-boyfriend back, enrolls in Harvard Law School. Elle’s mission ends up shifting as she begins to fight against stereotypes against blondes and is determined to succeed as a lawyer. Elle Woods is now one of the most popular rom-com female characters, but Witherspoon almost played another iconic blonde six years earlier.

Reese Witherspoon reclining with her dog as Elle Woods in Legally Blonde

Reese Witherspoon’s Best Movies Ranked

From Legally Blonde to Walk The Line, Reese Witherspoon has been involved in several great movies. But which ones are her best?

Reese Witherspoon Almost Played Cher In Clueless

Reese Witherspoon Came Very Close To Playing The Main Character In Clueless

Cluelessintroduced viewers to Cher Horowitz, a rich high-school student coping with adolescence and its problems in her very unique (and privileged) way.

Back in 1995, the coming-of-age teen rom-comCluelesswas released. Directed by Amy Heckerling and a loose adaptation of Jane Austen’s 1815 novelEmma,Cluelessintroduced viewers to Cher Horowitz (Alicia Silverstone), a rich high-school student coping with adolescence and its problems in her very unique (and privileged) way. Cher and her best friend Dionne (Stacey Dash) decide to help new student Tai (Brittany Murphy) blend in and gain popularity, and in the process, Cher learns a lot about herself, friendships, and her hidden feelings for someone close to her.

Alicia Silverstone as Cher gives a speech in Clueless.

WhenCluelesswas in development at Fox, studio executives suggested different, well-known actresses.

Although Silverstone was already known by then for her appearance in different Aerosmith music videos,Cluelesswas her big break on the big screen, but the role almost wasn’t hers. WhenCluelesswas in development at Fox, studio executives suggested different, well-known actresses, among them Keri Russell, Tiffany Thiessen, and Angelina Jolie.Heckerling met with Reese Witherspoon(viaVanity Fair) because she was told she was “amazing” and was “going to be huge”, but she had her mind set on Silverstone after watching her in Aerosmith’s music videos.

Clueless Alicia Silverstone as Cher looking confused and happy

Despite their more well-known suggestions, the studio didn’t pressure Heckerling to choose a big star, and she got to cast Silverstone as Cher. Witherspoon didn’t have any projects released in 1995, but in 1996 she starred in the black comedyFreewayand the psychological thrillerFear.Both Witherspoon and Silverstone became rom-com royaltyand two of the most beloved blonde characters in the genre thanks to their sense of humor and how they stayed true to themselves at all times. Silverstone didn’t reprise her role as Cher in the TV series, butWitherspoon returned as Elle inLegally Blonde 2: Red, White & Blonde.

Convincing Theory Claims This 2001 Movie Was A Secret Clueless Sequel 6 Years Later

Clueless never got a proper sequel, but a theory claims that a rom-com released in 2001 is a secret sequel, revealing what happened to Cher.

Will Reese Witherspoon Return As Elle Woods In Legally Blonde 3?

Legally Blonde’s Film Future Is Unclear

Legally Blonde’s success spawned a franchise with a sequel, three TV movies, a stage musical, and a series of teenage novels, but Witherspoon only returned for the direct sequel to the first movie.A third installment in theLegally Blondemovie serieshas been in development since 2018 and was going to be released in 2020. In May 2020, it was saidLegally Blonde 3was being rewritten, and in 2023, it was announced that Amazon was planning to produce the film and a TV series.

TheLegally Blondefranchise will expand with a prequel TV series titledElle, which will follow a young Elle Woods as a teenager, with the unique personality and ingenuity that has won the hearts of the audience. At the time of writing, no actress has been cast as young Elle Woods, and the future ofLegally Blonde 3is unclear.

Elle walks away from Chutney on the witness stand in surprise in Legally Blonde