Rebel Wilson's romantic comedy "Isn't It Romantic" hits theaters this Valentine's Day Eve — Feb. 13, 2019! But before we grab our date and head to the theater to see Rebel (and co-stars Liam Hemsworth, Priyanka Chopra, Adam Devine and more), Wonderwall.com is taking a look back at the leading ladies who came before her and ranking our very favorites. Did yours make the list? Keep reading to find out!
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No. 20: Melanie Smooter in "Sweet Home Alabama"
Pulling up the rear on our list? Good ol' Southern girl Melanie Smooter from "Sweet Home Alabama" (though we blame the flick for giving us the unrealistic expectation that our proposal might include being taken to an empty Tiffany store to pick out a ring!). This 2002 movie featured one of our favorite rom-com stars, Reese Witherspoon, playing the former poor girl-turned-fashion designer Melanie Carmichael. With that quintessentially glam rom-com day job, Melanie fits right in with most of the ladies on this list. The love triangle between her high school sweetheart (Josh Lucas) and rich new beau (Patrick Dempsey), though not the most original, sets the scene for a sweet and sentimental story that we've seen way too many times.
No. 19: Jamie Rellis in "Friends With Benefits"
Back in 2011, there was a war of nearly identical movies about guys and girls trying to hook up and stay friends. In our book, Mila Kunis and Justin Timberlake's "Friends With Benefits" came out victorious over the Natalie Portman and Ashton Kutcher rom-com "No Strings Attached" (though kudos to them for naming their flick after a song from Justin's old group *NSYNC!). One reason? Mila's cool character. Though the films were pretty similar, Mila's Jamie Rellis not only has a realistic job for a rom-com leading lady — she's an executive recruiter — but also has realistic expectations about love and some very relatable relationship baggage in her past. And minus the flash mob set to "Closing Time" at the end, Jamie's pal-to-boyfriend tale is one that might actually happen in real life!
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No. 18: Anna Scott in "Notting Hill"
Next up is a girl who was just standing in front of a boy, asking him to love her: Julia Roberts as Anna Scott in the 1999 romantic comedy "Notting Hill." Movie star Anna isn't always the most likable, especially compared to Hugh Grant's quirky, irresistible, bookstore-owning William Thacker, but their girl-meets-boy love story's ending alone solidified her spot on the list.
No. 17: Violet Sanford in "Coyote Ugly"
Piper Perabo as Violet Sanford in 2000's "Coyote Ugly" takes the next spot thanks to her sweet songwriting skills and even sweeter relationship with cutie pie Kevin (Adam Garcia). It had a killer soundtrack, but we also think watching Violet overcome her stage fright and work in the famous bar Coyote Ugly made for an entirely underrated rom-com back in the early '00s.
No. 16: Laney Boggs in "She's All That"
Let's face it, Laney Boggs (played by Rachael Leigh Cook) was gorgeous before she ditched the glasses and tweezed her eyebrows. The unpopular art student might have been duped by popular kid Zack Siler in "She's All That," but he couldn't help but fall in love with her in the process. And even though she lost, she'll always be the prom queen in our eyes!
No. 15: Jenna Rink in "13 Going on 30"
Next up is the delightful teen-turned-30 year old Jenna Rink! We all fell in love with Jennifer Garner in 2004's "13 Going on 30." Watching Jenna navigate life as a 13 year old trapped in a 30 year old's body resulted in plenty of laughs, and her sweet time-traveling romance with Mark Ruffalo's Matt certainly didn't hurt!
No. 14: Toula Portokalos in "My Big Fat Greek Wedding"
2002's "My Big Fat Greek Wedding" featured the lovable Toula Portokalos (played by Nia Vardalos), a dutiful Greek daughter still living with her parents and working at their restaurant at age 30, as she falls for customer (and non-Greek) Ian Miller ("Sex and the City"-era John Corbett aka Aidan). Like many romantic comedies, this one features a makeover — ditching glasses for contacts, a new wardrobe — but Toula gains confidence by taking computer classes too, setting this apart from other stereotypical plot points in the genre. She goes from working at her family's restaurant to her aunt's travel agency, where she once again bumps into Ian, subsequently falls in love and eventually gets her (hilarious) traditional Greek wedding.
No. 13: Olive Penderghast in "Easy A"
"Easy A" character Olive Penderghast makes the list thanks to Emma Stone's portrayal of the modern-day Hester Prynne. The funny 2010 flick, which was partially inspired by "The Scarlet Letter," features Olive lying about losing her virginity then subsequently becoming known as the school's resident tramp. She uses this newfound infamy to help other kids in school become more popular by lying about their encounters in a hilarious exchange for gift cards. From the entrepreneurial way she used her new popularity to her sweet relationship with Todd (played by a "Gossip Girl"-era Penn Badgley), we loved everything about Olive.
No. 12: Rachel Chu in "Crazy Rich Asians"
Constance Wu brought Rachel Chu to life as "Crazy Rich Asians" transitioned from book to the big screen in 2018. Brainy NYU professor Rachel is transported to a whole new world — the glitzy and glamorous Singapore high-society scene — thanks to her wealthy beau Nick Young (the beautiful Henry Golding in his first acting role). With an amazing makeover scene featuring plenty of couture, a sweet reminder of the importance of family and that hunky onscreen boyfriend, we loved everything about this movie — and strong, smart, independent Rachel.
No. 11: Josie Geller in "Never Been Kissed"
Oh, Josie Grossie! Drew Barrymore's "Never Been Kissed" character from the 1999 romantic comedy has never been kissed let alone had a boyfriend. As reporter Josie Geller goes undercover at a local high school for an assignment, she ends up falling hard for her English teacher, Sam, played by Michael Vartan. And that whole thing about Sam actually thinking she's a student throws a wrench in their romance plans. We loved seeing the sweet, naive Josie navigate high school for the second time around — and that kiss on the baseball field at the end goes down as one of the best in rom-com history!
No. 10: Jane Adler in "It's Complicated"
This list wouldn't be complete without Meryl Streep. Our favorite rom-com character played by the silver-screen queen was stylish bakery owner Jane in 2009's "It's Complicated." From her dreamy day job to her drool-worthy Nancy Meyers movie kitchen, the character explores romance after divorce and finds love with both ex-husband Jake (Alec Baldwin) and architect Adam (Steve Martin), who's hired to remodel her (already amazing!) Santa Barbara, California, home. Basically, Jane snagged her spot on this list thanks to her sweet job, two men fighting over her, her phenomenal house and having John Krasinski's Harley as a son-in-law. Lucky lady!
No. 9: Kat Stratford in "10 Things I Hate About You"
One of the coolest leads in teen rom-com history? The intimidating Kat Stratford (Julia Stiles, left) from "10 Things I Hate About You." In the modernization of Shakespeare's "The Taming of the Shrew," Kat's the resident shrew, an intimidating but impossibly cool high schooler who's antisocial and has no desire to date. But when sister Bianca (Larisa Oleynik, right) wants to start dating, she's told she can't until Kat finds a suitor — so Bianca's potential boyfriends attempt to find someone to tame rocker Kat. Enter resident bad boy Patrick Verona (the late Heath Ledger). There's plenty of hilarity and sweet moments as these two surprisingly fall in love (and hate).
No. 8: Vivian Ward in "Pretty Woman"
We'd be remiss not to include the main character in one of the classics, "Pretty Woman." Julia Roberts' portrayal of Vivian Ward — the prostitute who lives a fairy tale in this quintessential Gary Marshall romantic comedy — easily nabs the No. 8 spot on our list. The street smart, straightforward lady has gumption, and instead of letting rich and powerful businessman Edward (Richard Gere) swoop in and rescue her, she "rescues him right back."
No. 7: Cher Horowitz in "Clueless"
A total Betty gets our next spot — Alicia Silverstone as Cher Horowitz in "Clueless." The 1995 flick featured one of our all-time favorite ladies living life as a chic high school student in Beverly Hills. The film, which is loosely based on another classic tale, Jane Austen's "Emma," followed the adorably aloof Cher through her misadventures, including falling in love with stepbrother Josh (played by Paul Rudd — who could blame her?!).
No. 6: Bridget Jones in "Bridget Jones's Diary"
2001 saw "Bridget Jones's Diary" deliver a less glamorous take on finding love through the eyes of very single 32-year-old Brit Bridget Jones. She discovers her work crush, who also happens to be her boss, Daniel Cleaver (played by Hugh Grant), might have feelings for her, but also strikes up a surprising relationship with old family friend Mark Darcy (Colin Firth). Quirky, lovable Bridget spawned two sequels — 2004's "Bridget Jones: The Edge of Reason" and 2016's "Bridget Jones's Baby" — and easily earned a spot on the list.
No. 5: Mary Fiore in "The Wedding Planner"
"Those who can't wed, plan!" Jennifer Lopez has tons of rom-com characters to choose from in her past, but "The Wedding Planner" leading lady Mary Fiore reigns supreme in our hearts. She not only had two amazing suitors (Justin Chambers' Massimo giving her that dollhouse still kills us!), but she kept things professional even when faced with actual hunky lifesaver-turned-client Eddie (Matthew McConaughey).
No. 4: Holly Golightly in "Breakfast at Tiffany's"
That little black dress! Her dreamy breakfast routine! Audrey Hepburn's carefree and eternally cool Holly Golightly gets a spot on the list (despite ditching her cat in the rain). "Breakfast at Tiffany's" made us fall in love with this whimsical character who tries hard not to but eventually falls in love with George Peppard's Paul Varjak while playing by her own oddball rules.
No. 3: Andie Anderson in "How to Lose a Guy in 10 Days"
Perhaps the defining romantic comedy of the '00s, "How To Lose A Guy In 10 Days," made us all dream of being a writer for a women's magazine tasked with making Matthew McConaughey's Benjamin Barry fall in love and subsequently dump us. Unfortunately, there was only one pair of shoes to fill, and Kate Hudson stepped in as Andie Anderson. She earns major points for her painfully accurate portrayal of mistakes women make in relationships and for having the fortitude to walk away from an early-'00s-era Matthew. Bonus points for having us so engrossed in their sweet love story that we missed their insane rom-com alliterative names.
No. 2: Sally Albright in "When Harry Met Sally"
Picky eater Sally Albright had an unconventional road to romance with Harry Burns (Billy Crystal) in "When Harry Met Sally," but her quirky character remains one of our favorites to date and earns the runner-up spot on this list of our favorite rom-com leading ladies. An adorable Meg Ryan brought Sally to life in 1989, and she made us look twice at our guy friends and dream of having that one momentous New Year's Eve kiss.
No. 1: Elle Woods in "Legally Blonde"
Drum roll, please! Our favorite rom-com leading lady of all time? The one and only Elle Woods! We fell in love with "Legally Blonde" back in 2001 watching Elle (Reese Witherspoon) triumph on her sparkling pink path to Harvard Law School. From besting ex Warner Huntington III (Matthew Davis) to fashionably conquering law school one scented resume at a time to finding a much better suited beau in Emmett (Luke Wilson), the brilliant blonde always remained true to her cosmo-loving self. For that reason, she takes the top spot and remains one of our favorite role models.