Twenty years ago this month, a blond Harvard law student who unapologetically loved Barbie colors, manicures, blowouts and scented résumés entered our cinemas and won over hearts. 

The 2001 film Legally Blonde starred Reese Witherspoon as Elle Woods, a woman who initially applies to Harvard Law School to win back her college boyfriend, Warner, who broke up with her for not being serious enough. When Elle realises that Warner will never think she’s good enough, she decides to become a lawyer herself and prove her haters wrong.

Her quest to become a lawyer despite snobby fellow students and sceptical friends, family and law professors became a media franchise that includes a movie sequel, Broadway musical and a future third film. Elle Woods has been referenced in an Ariana Grande video and became a career inspiration to women.

Witherspoon told an interviewer in 2017, “At least once a week I have a woman come up to me and say, ‘I went to law school because of Legally Blonde.’” 

But what about Legally Blonde stills hold up when it comes to its messages about career and work? When I first watched the film as a kid, I remember being dazzled by Elle’s pink glittery outfits and oohing at her courtroom triumph when she used her knowledge of perm maintenance to help win a murder case. 

Now, in 2021, clunky Mac desktop computers are no longer en vogue and the early 2000s fashion – Tiffany necklaces and all – feels nostalgic. But there’s still a lot of the film that remains relevant. Here’s what still rings true – and what definitely doesn’t – about the film’s take on careers and success. 

It accurately portrays how cultural fit and connections can matter more than grades. 

When ex-boyfriend Warner condescendingly tells Elle she won’t get the coveted internship he wants because “You’re not smart enough, sweetie,” Elle shoots back, “Did we not get into the same law school, Warner? … We took the same LSATs and we’re taking the same classes.” 

But left unspoken in the film is that Elle and Warner, who attended the same California university and likely did a lot of the same extracurriculars as other wealthy white college students, also share a similar pedigree that helped them get into an elite law school. 

We find out that Warner, who has multiple politicians in his family, had his dad place a call to get him off of the waitlist at Harvard. But Elle used her connections, too, just ones that are less appreciated by this patriarchal society. To stand out from the crowd of Harvard applicants, Elle hires “a Coppola” to direct a video admissions essay of herself in a hot tub and around her sorority house.

Shocked and awed at the sight of Elle, the all-white male Harvard admissions board comes to quick agreement to take a chance on Elle, pointing out that she has been in a Ricky Martin video and is a faux fur panty designer. “Aren’t we always looking for diversity?” one quips. 

The scene inadvertently shows how ridiculous elite admissions processes can be, relying on irrelevant, subjective factors like extracurriculars and personal networks to make life-changing decisions about who belongs in an institution. Using the metric of cultural fit over who has real aptitude for the position is an unfortunately real practice outside of movies, too, and it’s a dynamic Legally Blonde captures well. 

It nails the betrayal felt when quid pro quo happens in the workplace.

Long before the #MeToo movement, Legally Blonde confronted sexual harassment in the workplace. Callahan, the law professor who mentored Elle in her internship, asks to see her alone in his office. 

First, Callahan praises Elle’s courtroom skills, saying she will be a great lawyer for following her instincts, then asks if she has considered her career path. Elle says she has not but that she knows getting a summer associate job is competitive. Callahan explains that competition is really about “knowing exactly what you want and how far you will go to get it. How far will Elle go?” before putting an unwanted hand on her thigh. Elle throws off his hand and storms off.

The subtext is clear: Callahan’s support for getting an associate job is conditional upon Elle accepting his harassment. It’s a textbook case of quid pro quo sexual harassment, in which opportunities for advancement are conditioned on submission to unwelcome sexual advances. The harassment derails Elle’s confidence in herself and almost causes her to drop out of law school because she becomes convinced Callahan gave her the internship only because he saw her as a “piece of ass.”

But at the beauty salon, Elle meets another professor, Stromwell, played by Holland Taylor, who delivers the movie’s iconic pep talk: “If you’re going to let one stupid prick ruin your life, you’re not the girl I thought you were.” 

As a result, Elle stays true to herself, gets hired to represent a client over Callahan’s objections and does end up graduating from law school with a prestigious job lined up. Elle has her success story, but Callahan’s move shows the challenges women face that can take them out of their careers before they even begin. 

But it doesn’t acknowledge the cruel abuse of power Elle exercises over a witness in a key scene…

Throughout the film, Elle’s knowledge of beauty, makeup and designer fashion is underestimated, even though it’s a valuable asset that helps clear her client’s name in the film’s climactic moment.

Legally Blonde successfully shows that the smarts that can make you successful in your chosen profession can come from many experiences, not just from the advanced degrees already earned by Elle’s snobby, educated classmates.

But one key scene feels jarring now to watch. During the murder trial in which she assists, Elle makes a broad assumption that only a gay man would know that her shoes are Prada and believes this would refute the prosecution’s narrative that Elle’s client and a pool worker named Enrique are having an affair to swindle the victim. Elle gets another law student to out Enrique during his testimony by asking Enrique what his boyfriend’s name is, and he answers. 

Enrique’s outing is framed as a rah-rah moment of feminist triumph for Elle, who used knowledge possessed by none of the lead male attorneys around her to help their client. But the fact Elle facilitates outing someone else takes me out of the movie now. It makes me feel queasy to see Enrique Salvatore, the only Latinx queer character in the film with a speaking role, outed so cruelly.  

…and Legally Blonde completely fails on the racial and ethnic diversity of a real student body. 

Elle the intrepid first-year law student embodies a power fantasy that you can embrace your femininity and love pink and still get ahead in your career, but ultimately it is a fantasy reserved for white women. The absence of people of colour in Elle’s Harvard student body is glaring. In 2004, when the movie is supposed to take place, the real Harvard Law School wasn’t as white as the one Legally Blonde depicted. As writer Ella Ceron points out, that year Harvard  Law was about 52% students of colour. The incoming class of 2023 is 47% students of colour and 17% LGBTQ students. 

Ultimately, I still laugh and smile at Elle’s journey to becoming a woman who owns her ambition, and who will roar triumphantly when she finds out she gets a coveted internship that her no-good ex said she was not smart enough to get.

But I can longer buy Elle as an outsider. The film frames her as a cultural outlier at her law school because she is from California, wears bright pink, and has a perky, cheerful personality compared to her insular East Coast student peers who dress in muted, dull colors. But now I see that when you take away her colourful outfits and accessories, Elle Woods is not all that different from the status quo of the people in power she wants to join. She fits right in.