In many romantic comedies, beloved protagonists find themselves up against formidable foes and vindictive villains alike. Whether it be a disapproving parent, an envious ex, or simply put, a miserable partner, these films provide examples of real-life red flags, for better or for worse.
Many budding couples recognize the various obstacles between them and a life-long union of love. Restricted by societal expectations and overwhelmed with a myriad of less than ideal opinions on love, dating, and marriage, navigating an experience as profound as love is anything but feasible. However, films tend to hone in on one or a few characters that are uniquely devious in their plots to prevent true love from being experienced.
A trend as such seemingly boomed in the early 2000s. With films ripe with misogyny both casual and otherwise, many have looked back on characters in films such as The Devil Wears Prada with a sour taste in their mouths. Depending on the demographic, the villain of the film might differ from person to person, with undesirable traits of today being brushed off as the status quo of yesteryears. These select films, nonetheless, have a wide range of maliciousness that fans have been eager to explore.
10 Gen (To All The Boys I've Loved Before)
To All The Boys I've Loved Before made its mark as one of the more successful rom-roms in the streaming era. For better or for worse the film finds teenager Lara Jean Covey (Lana Condor) in quite the dilemma after letters detailing her crushes on various boys in her life are mailed out to said crushes. The film focuses on Lara's budding relationship with Peter Kavinsky (Noah Centineo), one of the students she admired.
Drama ensues after her former friend Gen (Emilija Baranac) shows a renewed interest in Peter, given that the two were a couple before she broke up with him. Consistently toying with her Lara Jean and Peter, Gen's antics range from daily taunting, recording and posting an intimate kiss shared between Lara Jean and Peter, and implying that Peter cheated on Lara Jean with her. While her justification stems from a seventh grade betrayal, Gen is undeniably cruel to Lara Jean up until their reconciliation in subsequent installments.
9 Viola Fields (Monster-In-Law)
One of the worst fears for a spouse is to learn of a parent-in-law's disapproval of their love. The tense situation fosters up feelings of resentment, envy, and self-doubt. Monster-In-Law finds protagonist Charlotte "Charlie" Cantilini (Jennifer Lopez) in attempting to wed her beloved Kevin (Michael Vartan), while trying to get on her mother-in-law Viola's (Jane Fonda) good side. Introduced as a fashion designer in the making, Charlie sustains herself by waking dogs, working as a temp, and instructing yoga classes. Not long after, she meets Kevin, a doctor, and the two fall in love.
Consequently, Kevin's mother Viola attempts to ruin the marriage, fulled by a supposed consideration for her son's happiness. Viola's schemes range from the simply mischievous to the unnecessary cruel. Wearing a lavish white dress to the wedding is an insulting decision that most brides fear. However, feeding Charlie nuts, despite the latter being allergic, is quite disturbing. Despite her evaluating her distasteful disdain for Charlie, it took a while for Viola to rectify the various, venomous deeds she committed and the contentious situations was resolved part in due to Charlie's eventual forgiveness and the compromise both women make.
8 Lucy (13 Going On 30)
High school bullying continues to be an experience that film has engaged with in a myriad of ways. Due to the seemingly universal experiences people have with bullying, multiple perspectives are explored in multiple genres. In 13 Going on 30, the film follows a simmering romance between Jenna Flank (Jennifer Garner) and Matt (Mark Ruffalo), a long life attraction interrupted by the unnecessarily cruel intervention of one Lucy "Tom-Tom" Wyman (Judy Greer).
With a desire to be popular, the "nerdy" Jenna Flank tries to appease Tom-Tom and her clique, "The Six Chicks". After a game of seven minutes in heaven gone-wrong, Jenna wishes to be popular, "thirty, flirty, and thriving" to be exact. She then goes to sleep and wakes up the next day as a fabulous fashion editor with a luxury apartment, a handsome husband, and a best friend who just so happens to be Lucy.
Despite Jenna's new role as the head of The Six Chicks, that does not prevent Lucy from double-crossing her, sabotaging her efforts to make things right with Matty, her parents, and her boss. Even a friendship with Jenna could not provide Lucy with a new opportunity to right her wrongs with the various people she has harmed throughout her life. While that is in part to Jenna's own transgressions in her alternate life, Lucy's refusal to change for the better would have occurred whether ot not Jenna's wish was fulfilled. Thus, Jenna's decision in regard to Lucy made the conclusion all the more satisfactory to watch.
7 Mark (Love, Actually)
Everyone on the internet has seen the floating GIF of a love struck Mark (Andrew Lincoln), standing outside the front door of Juliet's (Kiera Knightley) home, holding up a series of cue cards and expressing his love for her. Fans of the film, of Lincoln and Knightley, alongside those who have yet to watch Love, Actually seemingly adore Mark's profound declaration of love. However, until that scene occurs, Mark is a completely different man. Introduced in the second segment of the film, Mark is rather perturbing. In spite of his role as Peter's (Chiwetel Ejiofor) best man, he is rather rude to Juliet.
Even in elementary school settings, the idea that a girl is bullied by a boy too shy to profess his true feelings is a troubling assumption to make. To watch Mark not only lead with the impression that he does not like Juliet, but to then record Juliet and Juliet alone during her wedding was unsettling at the very least. Aside from Juliet, the film establishes that Peter and Mark were close friends and to betray his trust is another point of contention for fans of the film.
6 Warner (Legally Blonde)
Women and femmes across the world come into contact with a chauvinistic man who prides himself on aligning and maintaining the status quo. Some might experience this early in their childhood. For Elle Woods (Reese Witherspoon), it happened to be her college sweetheart Warner Huntington III (Matt Davis).
Legally Blonde opens with Elle and Warner breaking up, deeming her as someone not serious enough to complement his dreams of being a senator. However, her academic success is the first of many feats Elle accomplishes, rendering his argument false. Throughout the film, Warner's exhausting shallowness hangs in the distance of Elle's successes and shortcomings. Constantly disparaging Elle for her pursuit of knowledge and self-improvement, it was satisfying to see her achieve her goals while leaving him in the dust, especially considering his nepotism-fueled success.
While the film was a commercial and critical success at the time of its release, recent years saw the film experience a renewed interest and celebration. Conversations about the film's celebration of hyper feminity and feminism, taking a saccharine piece of advice such as "staying true to yourself" while achieving one's dreams and promoting it to a new audience with a different and engaging perspective. Through Warner and characters like Professor Callahan, the creator's critiques of misogyny are efficiently explored through their respective demises.
5 Michael Teo (Crazy Rich Asians)
As much as love is woven into the stories and the characters that make up the fantastic Crazy Rich Asians, the film also featured many conniving characters. From seemingly envious admirers of Nick (Henry Golding) to the icy Eleanor Young (Michelle), there were many characters that prayed for the demise of Nick and Rachel's (Constance Wu) relationship. From the moment Rachel arrived to the Young's lavish Singaporean estate, most of the attention remained focused on interrogating Rachel worthiness.
Nevertheless, there was another villainous character that the movie foes an excellent job of capturing. When in Singapore, Rachel and the audience are introduced to Nick's illustrious older sister Astrid (Gemma Chan) and her husband Michael (Pierre Png). Despite the both of them being wealthy, Michael experiences impostor syndrome due to his background as a self-made man. Coming from old money, Astrid's reputation precedes her and despite her otherwise welcoming and pleasant demeanor, MIchael fails to see how his insecurities hurts those around him.
After being exposed as a cheater, Michael tries to excuse his infidelity by shifting the blame onto Astrid, crediting her status as being the reason for his extramarital affair. Anyone with basic human decency could see through his excuse and as a viewer, it was satisfying to watch Astrid deconstruct his already faulty argument, prioritizing herself and her son over protecting their collective reputation.
4 Ben (He's Just Not That Into You)
Based on the self-help book of the same name, He's Just Not That Into You finds the lives of nine romantic partners evaluated in under 130 minutes. Centered around Gigi (Ginnifer Goodwin), the film finds her character's romantic mishaps as well as her various friends and their troubling relationships.
One in particular centers around Janine (Jennifer Connelly), Ben (Bradley Cooper), and Anna (Scarlett Johannson), a worrisome "love" triangle that ends in despair. In spite of his marriage to Janine, Ben begins an affair with Anna Marks, a yoga instructor with hopes of making it in the music industry. Not only is he unfaithful, but he appears nonchalant about everything from Janine's concern's about his smoking and to the affair with Anna itself. The smoking in particular is a sensitive issue that stems from the passing of Janine's father. While both women make decisions with the knowledge they come across by, Ben is left to deal with the aftermath of his disregard of Janine and Anna's feelings.
3 Marianne Bryant (Easy A)
Once every day film watchers learned that a modern retelling on Nathaniel Hawthorne's, Easy A surely earned itself a built-in audience. A young consumer base in search of a thought-provoking yet entertaining rom-com while older audiences sought to see if the movie would live up to the standards established by the original novel.
Comprised of an ensemble cast including Emma Stone, Amanda Bynes, Stanley Tucci, and Penn Badgely, the film follows seventeen-year old Olive Penderghast (Stone), a teenager whose reputation becomes shaped around her alleged promiscuity. Unlike most films, Olive uses lies and gossip for good, transforming herself and feeding into the rumors while helping her friends with even more dishonest distractions.
Marianne Bryant (Amanda Bynes) is the leader of the school's church group and is also responsible for spreading the rumor. Attempting to start another vanity project under the guise of genuine assistance, Marianne attempts to recruit Olive to no avail. As a result, the church group begin a harassment campaign targeted towards Olive in hopes of exiling her from the school.
While many may believe that America's days under Puritanism are long gone, films like Easy A and characters such as Marianne serve as prove that said beliefs have been woven into American society and have only recently been challenged.
2 Dex (Fire Island)
Much like many beloved rom-coms, Fire Island is an entertaining adaptation of a literary classic. The film finds lead actor and writer Joel Kim Booster alongside costars like Bowen Yang, Zane Phillips, and Margaret Cho in a lively, queer reinterpretation of the timeless "Pride and Prejudice". Joining the various adaptations and remakes of the novel, Fire Island's successful balance between comedy and seriousness makes it one of the more unique and fresh explorations of the Jane Austen novel.
The film follows a group of friends and their unimaginable vacation on the titular island, known for its long history as a gay village. Friendships are tested, love interests either rise up to the challenge or fail miserably, and important conversations about intersectionality take place during the eventful week. Topics such as consent and performative activism arise, tied to the inauthenic Dex, portrayed by Zane Phillips.
Introduced as a potential love interest to Noah (Booster), the admittedly attractive bachelor woos Noah during a grocery store visit and the two instantly hit it off, to the dismay of Will (Conrad Ricamora), one of Noah's friends. After everyone convenes for dinner, Will and Dex's animosity comes to life after the latter accuses Will of holding a negative stigma against sex workers.
However, as the film progresses, it is revealed that not only did Dex hurt a close friend of Will's, but he also uses social activism to promote said brand, and has no problem with violating the consent of his partners. After learning of his use of hashtags such as "#BlackLivesMatter" and "#StopAsianHate" and his uploading of an intimate moment shared between him and Luke (Matt Rogers), Noah, Will, and their friends confront Dex and threaten him with legal action.
What makes Dex, and the film at large, compelling are the contentious conversations and authentic experiences explored. People like Dex exist in real life and wield their desirability in ways that harm people. As David Fear penned in the Rolling Stone review of the film, the inclusion of "gay heroes, gay villains, and gay people of color galore" offers audiences an exquisite experimentation with the plots set forth by Jane Austen.
1 Joey (Ten Things I Hate About You)
10 Things I Hate About You continues to be commemorated for being one of the better 90s teen rom-coms. Starring and Julia Stiles and Heath Ledger, the film follows the burgeoning romance between Kat Stratford (Stiles) and new student Patrick Verona (Ledger). While the former is an outspoken progressive, the latter quickly earns a bad boy reputation. Their initial conversations seem to lead nowhere, but a burning passion binds the two of them. However, the high school setting invites both cliques and inflated egos to threaten both the growing relationship and the various friendships in the film.
No one poses a bigger threat than Joey Donner (Andrew Keegan), the most popular boy in Padua High School. His arrogance imposes a real danger to the girls around him and his status as the most popular student grants him a particular privilege that most viewers are aware of. Not only does Joey's transgressions include the eerily typical bullying but also includes violation of consent and personal boundaries. As viewers learn about Kat and Joey's past relationship, it is revealed that he pressured her into having sex and immediately broke up with her when she confessed to not being ready for that level of intimacy.
In depicting a seemingly mundane tale about an American high school, 10 Things I Hate About You takes the Shakespearean foundation of the film to highlight an often overlooked but glaring societal problems that first flourish in hierarchal high school systems.