It’s been 20 years since Reese Witherspoon “bent and snapped” her way to worldwide superstardom in Legally Blonde. The film follows fashion queen-turned-law student Elle Woods, a pink-obsessed blonde who enrolled in Harvard Law School to win back a man who dumped her, but then found a whole new calling along the way. Legally Blonde wasn’t Witherspoon’s first starring role: her critically acclaimed roles in Election (1999) and coming-of-age drama Man on the Moon (1999) came before it, as did her now-iconic role as abstinence-supporting virgin Annette Hargrove in Cruel Intentions (1999). Yet Witherspoon’s portrayal of Elle Woods was her first box office smash, with a string of one-liners making the film an important pop culture reference point, and turning her into a household name.
When Legally Blonde hit theaters, Elle Woods was endearing to people who had felt like they didn’t fit in, but particularly women who perhaps weren’t taken seriously or had their ambitions limited because of the way they spoke or dressed. It offers a quintessentially ’90s “looks can be deceiving” feminist narrative: a woman who defies expectations to turn heartbreak into #CareerGoals, while helping various women get payback on the men who have wronged them. Its crescendo is Elle winning a landmark murder trial (helped by her excellent “gaydar” and in-depth knowledge of perm techniques) and proving everyone who doubted her wrong―including her elitist ex-boyfriend and a creepy professor who hit on her. By the end of the film, she’s found a new love and a new passion (chihuahua-in-hand, of course).
Two decades on, Reese Witherspoon’s career has had similarly dramatic twists and turns. After winning a string of awards, including an Oscar for her portrayal of June Carter Cash in Walk the Line (2005), things began to fizzle. Despite being one of the highest-paid actresses in Hollywood at one point, she soon struggled to find roles which were similarly challenging and interesting. Witherspoon recalls reading script after script featuring submissive, dull women written by men, and later described herself as “a little bit lost” during this time. In 2013, an embarrassing video emerged of her being arrested while drunk and arguing with a police officer, yelling: “Don’t you know who I am?”
The lack of roles, combined with less-than-flattering press, created the public perception that Witherspoon (or her career, at least) was in a moment of crisis. And looking purely at her on-screen roles, from her breakthrough 20 years ago to her Oscar-winning role and resurgence era, portraying women on the edge is what she does best. “Rich woman in a crisis” is a particular trope that, from TV to film and stage, audiences can’t seem to get enough of, from reality TV shows like the Real Housewives and Keeping Up with the Kardashians, to dramas like Desperate Housewives and Sex and the City. Kirsten Dunst’s portrayal of Marie Antoinette, Nicole Kidman’s all gasp-filled role in The Others, and Kate Winslet in Titanic are other memorable examples, while pop culture has an enduring (and often-problematic) fascination with survivor women like Judy Garland and Britney Spears.
A common motif in these “crisis” stories is an iconic comeback. Witherspoon began plotting hers at the age of 36, when she founded her own production company and started buying the rights to books that featured characters and stories that she found compelling. (Her husband, talent agent Jim Toth, says he’s never met a more avid reader). “Women in crisis”—mostly of the wealthy, white variety—feature heavily in these stories. The first was Gone Girl (2014), a film about a woman who faked her own disappearance in order to frame her cheating husband. Witherspoon produced the film, which starred Rosamund Pike and Ben Affleck, with Pike receiving an Oscar nomination for the role. She then produced and starred in Wild (2014) which yielded Academy Award nominations for herself and Laura Dern, who played her mother. Next she optioned a novel by Liane Moriarty called Big Little Lies (2017), turning it into a critically acclaimed series she starred in alongside Nicole Kidman, Zoe Kravitz, Laura Dern, and Shailene Woodley. The show followed a group of women in a wealthy California coastal community who were bonded together by dark secrets.
At this point, Witherspoon had succeeded in making herself an influential star again, both in front of and behind the camera. She then executive produced and starred in The Morning Show (2019) alongside Jennifer Aniston, which went behind-the-scenes in a newsroom in the aftermath of a sexual harassment scandal, followed by book-inspired miniseries Little Fires Everywhere (2020).
Witherspoon’s roles have changed since Legally Blonde. Elle Woods was an early-stages #GirlBoss, of sorts, who made her way to success by doing things her own way in corrupt, elitist surroundings. Similarly, in Cruel Intentions, her character was the one beacon of decency and innocence in a world of obscene wealth and deception. But now the privileged women she brings to our screens aren’t just oppressed, but oppressors too. In Little Fires Everywhere, Witherspoon plays journalist, mother, and landlady Elena Richardson. Her character finds herself overwhelmed by the responsibilities and pressures of being a working mother. But she is also horrible to her queer teenage daughter and develops a thinly veiled racist obsession with her maid (Kerry Washington). Similarly, in Big Little Lies, she portrays a wealthy mother pushed to the edge, but who is deeply selfish with a very visible “Karen” streak, too.
Witherspoon’s nuanced portrayal of women who are a mixture of good and bad circumstances and choices—and are both victims and oppressors—aligns with shifts in feminism over the last decade. Similarly to marginalized groups like the LGBTQ+ community, there’s now an emphasis on intersectionality, where factors like class and race intersect with gender and sexuality. “White feminism”—a form of feminism that is accused of focusing on the struggles of white women, or “white feminists”, over other people—has been much derided. More white women voting for Donald Trump than Hillary Clinton in 2016, plus viral stories like Amy Cooper (aka “Central Park Karen”)―a self-described liberal who was filmed calling the police on a Black man who merely advised her to put a leash on her dog―have prompted conversations about how white womanhood can be weaponized against others.
Kemi Alemoru, culture editor at gal-dem―a publication for people of color from marginalized genders―sees this cultural shift in Witherspoon’s work. “In her most recent roles, where she shifts into increasing ‘Karenhood’ in Big Little Lies and Little Fires Everywhere, she has a lot more control over how the characters she plays are written and presented,” she tells The Daily Beast. “Instead of just discussing whether ‘women can be both brains and beauty,’ which is a fairly dated conversation, she’s looking at feminism and womanhood from the perspective of how women aren’t all the same: how they differ from each other along racial and class lines.”
Alemoru thinks this is an example of feminist discussions that were started by women of color seeping into mainstream popular culture. “I think a lot of conversations around intersectionality have forced an examination of where privileged white women sit in society, compared to other women,” she says. “But it’s good that, now she’s in the driver’s seat, Reese is exploring that and is trying to think of the best ways to examine women on screen who aren’t necessarily like her.”
It’s true that Witherspoon’s era of resurgence has focused on class and the often brutal ways it operates in America. In Wild, her standout and most unique role, she plays a struggling waitress who grew up in an abusive household and turned to drugs in the aftermath of her mother’s death. Perhaps if Witherspoon remade Legally Blonde today, it might nod to the fall of #GirlBoss culture in some way, or acknowledge that Elle’s ascension to Harvard was benefited by having rich parents (even if she did pooh-pooh snobbery when she arrived). Maybe we’ll see hints of that in Legally Blonde 3, expected next year, but it’s also possible that the absence of self-awareness and realism was part of the 2001 film’s charm.
Reese Witherspoon stars in Big Little Lies
HBOWitherspoon’s work behind the scenes is even more significant than her on-screen portrayals (when it comes to addressing inequality, at least). When she started out, she can remember being in films where she was the only woman on the set with 150 men. “Maybe there would be a couple of women in wardrobe. I remember when I was a kid I would find them and cling to them,” she told Vanity Fair last year. This is something she set out to change. Originally she was motivated by creating work for herself, but after her move to TV she eventually won an equal pay agreement from HBO, which benefited other women. “An actress came up to me at a party and said, ‘Do you know what you’ve done?’ I had no idea what she was talking about,” she remembers. “The day after the HBO equal pay thing went through, they called her agent to rewrite her contract. She was then paid twice as much as she had been.”
Witherspoon’s resurgence in prestige TV is part of an important shift. Once there was a perceived difference (and hierarchy) between “TV actors” and “movie stars.” But in the streaming era it is no longer unusual or shameful for film stars to be on TV. Hollywood royalty Meryl Streep’s role in Season 2 of Big Little Lies exemplifies this change, just like Nicole Kidman in The Undoing (2020) and Kate Winslet in Mare of Easttown (2021). This isn’t down to Witherspoon alone, of course, but it’s hard to imagine such a prevalence of starring roles for women, particularly in their forties and fifties, without her oh-so-bankable success.
In the 20 years since Legally Blonde, where Witherspoon played a character who refused to be sold short, she has embodied a similar survivor spirit in an industry known for discarding and mistreating women who go against the grain. Now in the driver’s seat of her own career and narrative, it feels like the woman Vogue described as “Hollywood’s moral compass” is just getting started. The roles she brings to the screen now might offer a more complex, nuanced and even critical look at how women navigate the world, but her breakout role was our first warning never to underestimate Reese Witherspoon.
