Calling all Cosmo Girls, Legally Blonde is turning 20! Reese Witherspoon bounced into our hearts in 2001 as the blonde-haired, bright-eyed Elle Woods, and now, 20 years later, we’re still in love with the smart and sassy Gemini-vegetarian from California.
Legally Blonde follows Elle’s journey from California sorority house to Harvard Law School, where she immediately stands out as a Malibu Barbie among a sea of plaid. Elle is there to win back the heart of the man she loves by proving to him that she’s serious enough to be marriage material, and not even his surprise engagement to a Vanderbilt-prototype named Vivian can stand in Elle’s way. If you fell in love with the unstoppable girl-power of Elle Woods, like to root for the underdog, and just flat out enjoy a feminist storyline disguised as light-hearted girliness, then you’ll love the movies on the list. To celebrate 20 years of Legally Blonde, we’ve got 20 entries here for you to check out.
Legally Blonde 2: Red, White & Blonde
Legally Blonde 2: Red, White & Blonde is an obvious pick for this list, as we definitely want to know what’s next for Elle Woods: Former Miss Hawaiian Tropic and brand new lawyer. Red, White & Blonde takes Elle all the way to our nation’s capital, where she fights for legislation protecting animals from harmful testing, even putting her wedding on hold to take on this venture. We get all the Elle Woods charm we enjoy from the original movie, along with a few of our favorite returning characters including Paulette (Jennifer Coolidge) and Emmett (Luke Wilson).
Election
Just a few years before Legally Blonde, Reese Witherspoon was portraying another ambitious young woman with her eye on a future in politics. While not as friendly as Elle Woods, Witherspoon’s Tracy Flick is certainly as determined. Tracy is campaigning for class president at her small high school, and when one of her teachers (Matthew Broderick) tries to prevent her from winning, the election becomes ruthless. For an irresistibly single-minded Reese Witherspoon and a nostalgic high school setting, check out Election.
Mean Girls
Another high school-based storyline with a female-centric cast and the wit of Legally Blonde, Mean Girls is of cult-classic status these days. Like Elle Woods, Cady Heron (pronounced kay-dee) is the new girl in school and an outsider among her peers, seeking acceptance with the popular clique on campus. Plenty of early 2000s fashion and quotable one-liners are included in this film, with Tina Fey and Amy Poehler among the many SNL alumni that are part of the production.
The Devil Wears Prada
The Devil Wears Prada features Meryl Streep as ultimate mean girl Miranda Priestly, editor in chief of the biggest fashion magazine in the world, with Anne Hathaway as her unfashionable and very out-of-place new assistant, Andy. If Andy’s ever going to make it in the foreign world of fashion, she’ll have to learn some hard lessons about her industry, her boss, and herself.
Drop Dead Gorgeous
Speaking of mean girls, there are quite a few of them in the 1999 comedy mockumentary Drop Dead Gorgeous. This film was ahead of its time and is another one rising to cult-classic status. Drop Dead Gorgeous features Kirsten Dunst and Denise Richards (also including Brittany Murphy and a young Amy Adams) among a handful of beauty pageant contestants followed by a documentary team, as the young ladies compete in small-town Minnesota. Kristie Alley steals the spotlight as a hilariously deranged pageant mom, going to great lengths to ensure her daughter’s crown and title. After watching Drop Dead Gorgeous, you’ll never look at parade floats the same again.
Miss Congeniality
Pageants, pageants, and more pageants! We’re onstage again in Miss Congeniality, starring Sandra Bullock as Gracie Hart, the most out-of-place girl at the Miss America competition. Gracie is an undercover FBI agent sent to the pageant to investigate mysterious threats made to the Miss America Organization, and to protect the women contestants. Sure, Agent Hart can drop a grown man with a swift punch to the throat, but she doesn’t know the first thing about pageants — or lipstick or high heels or dresses, for that matter. Where Elle Woods is a Barbie doll in a sea of plaid, Gracie Hart is a G.I. Joe in a forest of Elle Woods.
Pretty Woman
Pretty Woman is a classic 1990s romantic comedy starring Julia Roberts and Richard Gere, and features the iconic scene in a Beverly Hills fashion boutique where Julia Roberts — years before Witherspoon’s similarly sassy scene in Legally Blonde — tells off a snooty shopgirl. Watch Pretty Woman for the feisty Julia Roberts, stay for the fabulous ‘90s fashion.
My Best Friend’s Wedding
Another Julia Roberts ‘90s flick, My Best Friend’s Wedding has Roberts as Jules, a food critic trying to win the heart of her best friend (Dermot Mulroney) and convincing him to call off the wedding to his new fiancé, Kimmy (Cameron Diaz). Like Elle Woods and her rival Vivian, Jules and Kimmy couldn’t be more different, with Jules likening herself to the easy-going dessert choice “Jell-O,” and deeming Kimmy as the over-the-top “crème brûlée.” But which dessert will the groom choose? If you loved bending and snapping with Elle Woods in the salon, then get ready to sing Aretha Franklin in a seafood restaurant.
Bridesmaids
For some more wedding-centered rivalry, we have Bridesmaids up next on our list. Except, this competition for a spot at the altar isn’t a fight for the groom, but rather a fight for the coveted role of Maid of Honor. Kristen Wiig and Maya Rudolph head up the cast of funny ladies including Rose Byrne, Rebel Wilson, and Ellie Kemper, along with Melissa McCarthy stealing puppies and scenes left and right. For lots of laughs and feely-goods among girlfriends, give Bridesmaids a watch.
How to Lose a Guy in 10 Days
We saw Elle Woods try everything she can to snag the guy of her dreams, but what about driving a guy away? That’s exactly what Kate Hudson’s character, Andi, attempts to do in How to Lose a Guy in 10 Days. Andi works for a popular women’s magazine and has been assigned the task of charming a man (Matthew McConaughey) into falling head-over-heels for her, only for her to force him to dump her because of the silly antics she pulls. As Andi puts it, she’s basically writing a “How to Guide” for women of what not to do in a relationship. Andi oozes Elle-like ambition, and I like to think Andi and Elle would be blonde besties.
Romy and Michele's High School Reunion
We do get a couple of blonde-haired besties in the underrated 1997 gem Romy and Michele's High School Reunion. With their ten-year high school reunion suddenly upon them, and without much “success” to show for the last decade, what are Romy (Mira Sorvino) and Michele (Lisa Kudrow) to do? They’re sure to once again face their own high school’s clique of mean girls — a trio of very pregnant Vivien Kenzington/Regina George hybrids — and Romy and Michele refuse to be humiliated at their reunion. So, the solution is simple. Tell everyone you invented Post-It notes. That should work, right?
Never Been Kissed
We’re going back to high school again. This time, not for a reunion, but for an undercover story. Drew Barrymore is Josie Geller, a 25-year-old reporter for the Chicago Sun-Times and former bearer of the high school nickname, “Josie Grossie.” Josie’s getting a second chance to fit in among the groups where she was always an outsider, but she’s only got one chance to get the story. She might even get a chance at love along the way, too, ending the sting of her title status: Never Been Kissed.
Josie and the Pussycats
Josie and the Pussycats features Rachael Leigh Cook as a much hipper “Josie” (sorry, Drew Barrymore) and her pussycat bandmates — fellow early 2000s teen royalty Tara Reid and Rosario Dawson — on their journey to musical fame. Josie and the Pussycats are from the small town of Riverdale (the Riverdale of the Archie comics and its many TV spin-offs) and are shocked by their sudden musical success. If you were inspired by the climb taken by Elle Woods, then you’re sure to root for these authentic underdogs, too.
Clueless
Clueless is another cult classic celebrated for its iconic fashion, witty humor, and unabashedly-bubbly female lead. Cher Horowitz (Alicia Silverstone) is a Beverly Hills socialite, shopaholic, and wannabe matchmaker navigating her way through lessons in life and in love. Clueless is based on Jane Austen’s classic 1815 novel Emma, and superbly portrays the themes and characters from that work, while also setting the stage for an Elle Woods entrance a few years later. And I’m positive that Cher and Elle could easily be California neighbors, classmates, and friends.
10 Things I Hate About You
Next on our list, we have another film based on classic works, with the female lead that’s on the opposite end of the sparkle-spectrum from Elle Woods. 10 Things I Hate About You is based on The Taming of the Shrew by William Shakespeare, a point highlighted by lead characters Patrick Verona (Heath Ledger) and Kat Stratford (Julia Stiles) being named after cities relevant to Shakespeare. While Kat Stratford might be the brooding and sarcastic polar opposite of Elle Woods, Kat is unapologetically herself, no matter the judgment from her peers. Like Elle, Kat Stratford is refreshingly authentic, and you’ll soon find yourself rooting for her.
13 Going on 30
While a couple of the entries on our list explore the idea of going back to a time of life as a young person, 13 Going on 30 takes teenager Jenna (Christa B. Allen) forward in life (Jennifer Garner). After a birthday party gone horribly wrong, 13-year-old Jenna Rink makes a wish to skip all the in-between years and instantly become “thirty, flirty, and thriving” like the women she’s read about in her favorite fashion magazine. Jenna gets her wish, and awakens to an adult life where she has everything that teenage Jenna could’ve dreamt of. But will 13-year-old Jenna be proud of the “thriving” 30-year-old she’s become? For an appreciation of style on par with that of Elle Woods — along with a “Thriller” musical number that’s aaalmost as fun as the bend and snap — check out 13 Going on 30.
Uptown Girls
Uptown Girls has Brittany Murphy returning to this list (catch her in Clueless, too) as privileged party girl Molly, who is struck with the sudden reality of rent, bills, and adult life in general. It’s time for Molly to grow up and get serious, so she takes the job of nanny to eight-year-old Ray (Dakota Fanning), who soon proves to be more “mature” than Molly. If you’re in the mood for a lovely female-centric film about a friendship not bound by age, then you should try Uptown Girls.
Bring It On
This 2000 flick pairs Kirsten Dunst and Gabrielle Union in a competitive cheerleading world where neighboring high school rivalries and local competitions are cutthroat. Where Legally Blonde proves that there’s more to Elle than blonde hair and pink accessories, Bring It On shows us that there’s more to these California cheerleaders than jazz hands and stolen routines.
John Tucker Must Die
John Tucker Must Die portrays the joint forces of four high school girls from varying backgrounds and social cliques, bonded together in the shared effort of exacting revenge on the most popular boy in school, John Tucker (Jesse Metcalfe). Arielle Kebbel is Carrie, the brains of the operation; Ashanti is Heather, the skilled cheerleader; Sophia Bush is Beth, the hipster activist; and Brittany Snow is Kate, the new girl in school and latest object of John Tucker’s affection. Together they devise a plan to teach John Tucker a lesson — a lesson in underestimating women. For some fun girl-power and plotting, check out John Tucker Must Die.
Charlie’s Angels (2000)
The last entry here returns Cameron Diaz and Drew Barrymore to our list, as they — along with Lucy Liu — give new life to the legendary cool chicks, Charlie’s Angels. If you love the way Elle Woods serves up lewks while simultaneously serving up justice in the courtroom, then you’ll also enjoy the stylish crime-fighting Charlie’s Angels in all its cheeky 2000s fun.