Reese Witherspoon Once Felt Like ‘Only One Girl Could Make It.’ How Roles In Election And Pleasantville Changed Her Life

Reese Witherspoon as Jennifer in 1998's Pleasantville
(Image credit: New Line Cinema, Warner Bros)

Reese Witherspoon, a beloved entertainer known for her exceptional performances and one of the most iconic actresses of the 1990s, gained fame with notable roles in films such as Cruel Intentions (which she helped write), Election and Pleasantville. Amid her continued success, the Sweet Home Alabama star opened up about her difficulties as a young actress in a candid interview. As she explained, these breakthrough roles shaped her career and transformed her perspective on the possibilities available to women in the entertainment industry.

The actress' journey to A-list status was not without its obstacles, as you'd probably imagine. While sitting down with Harper's Bazaar, the star of The Morning Show, which has been renewed for a fourth season, reflected on her early competitive nature and acknowledged her lack of support for other women in Hollywood. She attributed this behavior to her own jealousy and frustration with limited career opportunities: 

I was really unhappy. I was not seeing the abundance of opportunity.

Reese Witherspoon revealed her strong pursuit of roles she ultimately didn't secure, including Clueless and Baz Luhrmann's smash hit about forbidden love, Romeo + Juliet. She expresses her intense desire for the latter, acknowledging her devastation at coming close to landing the role: 

Oh my God, I wanted to do Romeo + Juliet so badly, so badly. Of course, Claire Danes was amazing, but it was devastating to me that I didn’t get it after screen tests and getting really close.

Reflecting on her transformation, the Walk the Line star discussed how pivotal Election and Pleasantville were in shifting her career trajectory. With the role of Tracy Flick in particular, she created a character that defied industry stereotypes and challenged the notion that only one woman could thrive in Hollywood. This breakthrough performance earned critical acclaim and paved the way for her to receive more diverse opportunities. The A-lister added:

I got Election, and I created Tracy Flick, and I ended up being in Pleasantville, which was amazing. Ava [her daughter] was asking me the other day about where I come up with these characters, like Tracy Flick, Elle Woods, and [Melanie Smooter from] Sweet Home Alabama. I created them all within the span of five, six years in my 20s. …Sometimes, I look back and go, ‘How the hell did I do that?’

Reese Witherspoon as Elle Woods in Legally Blonde.

(Image credit: Twentieth Century Fox)

Following these breakout roles (which still rank amongst Reese Witherspoon's best movies) and exploration of self-help literature, the Wild star experienced a profound transformation. However, the most pivotal moment came when she became pregnant with her daughter, Ava, at 22. Recognizing her potential influence as a role model for her child, Witherspoon embarked on self-improvement and introspection. Guided by the question, "Who do I want my daughter to see?” She committed herself to becoming a woman worthy of admiration. This process required her dedicated efforts and commitment to personal growth, she recalled: 

Boy, I read a lot of self-help.

After giving birth to her daughter, the Oscar Winner experienced a profound shift in self-confidence and a clear purpose: to challenge the male-dominated Hollywood landscape by creating stories centered around women. With the establishment of her media and production company, Hello Sunshine, she has provided a platform for women to share their perspectives and experiences.

The Where the Crawdads Sing producer's journey to becoming a prominent producer began when she questioned the lack of diverse roles in Hollywood and decided to take matters into her own hands. By adapting novels like Wild, Big Little Lies (one of the best shows streaming on Max), and the Oscar-nominated thriller Gone Girl into successful projects, she showcased her keen eye for compelling stories and talent for matching writers with adaptations.

While she continues to take on complex roles, her commitment to empowering women has positioned her as a formidable presence in Hollywood. Approaching her 50s, she feels liberated from the opinions of others and prioritizes achieving her own goals. Reflecting on her journey, the actress shared:

I think you start to realize there’s a finite amount of time that you have to accomplish what you want to accomplish in this world and that worrying about other people’s opinions of you is a waste of your precious time. It’s a liberation in your 40s to feel free of other people’s opinions. I mean, they’re always there. They just don’t matter as much to you, and it’s a great feeling.

She's clearly thriving right now, and you love to see it. Fans can check out our list of upcoming Reese Witherspoon projects or see her continuing to showcase her acting prowess in the upcoming season of The Morning Show, which is slated to hit the 2023 TV schedule this fall. For those eager to catch up, the first two seasons of the captivating workplace drama are available for streaming with an Apple TV+ subscription. Pleasantville is also available to rent on Prime Video, while Election is streamable with a Hulu subscription.

Ryan LaBee
Writer

Ryan graduated from Missouri State University with a BA in English/Creative Writing. An expert in all things horror, Ryan enjoys covering a wide variety of topics. He's also a lifelong comic book fan and an avid watcher of Game of Thrones and House of the Dragon.