I am a firm believer that the 90s and early 2000s were the golden age for romantic comedies. As your average twenty year old girl that falls prey to romanticizing literally everything in her life, these films are a continuous comfort. By living vicariously through grand gestures, curtain bangs and fashion trends that never die, it feels as if the era is immortalized in these classic films. I have by no means reached the status of an expert having only scratched the surface of iconic rom coms. However, the following are my current top five, ranked based on how entertaining they are and how likely I am to watch them again in spite of how many times I’ve already seen them.
5. First Daughter (Whitaker, 2004)
Katie Holmes’ performance as the witty and generous Samantha Mackenzie had me waiting for the other shoe to drop. And then it did (but not in the way I expected). Our initial impression of Sam is that she is charming and down to earth, simply wishing to live out her normal college girl experience, and it led me to believe that the plot’s conflict would involve a scenario in which her friends discovered that she was in fact more self-centered than she let on. My surprise was genuine (my jaw was on the floor) when the plot’s real twist was uncovered in a challenge posed to the protagonist that struck much more intimately to her personal trust and vulnerability. An issue that spoke to common teenage struggles rather than her status as the ‘First Daughter’. The smoothness of the plot continuation, cleverly contrasted by the sharpness of the plot twist, unusual for your typical rom com, is what genuinely impressed me, and it had me returning for multiple rewatches.
Number of rewatches: 3
4. She’s The Man (Fickman, 2006)
This stellar performance from Y2K favourites, Amanda Bynes and Channing Tatum (but mostly Amanda Bynes), recreates in – in stunning 21st century humour – the popular Shakespeare comedy Twelfth Knight. I found the progression of the romance plot to be a little rushed, but this is wholly made up for in quick-paced, sharp dialogues and jokes that are still part of my daily vocabulary. Most importantly however, despite not exhibiting typical ‘feminine’ attributes and generally adopting a ‘not-like-other-girls’ personality, Viola does not sacrifice her goal of proving wrong those who discredited her for her gender when she develops a romantic interest. Unlike other romantic comedies that have shown the protagonist undergoing a severe transformation so as to be acknowledged by their peers, Viola stays true to herself and delivers an important message spiting gender discrimination in the pursuit of her original goal.
Number of rewatches: 3
3. Bridget Jones’ Diary (Maguire, 2001)
I will be the first to admit that this film aged terribly. It promotes an awful late nineties dieting culture and a very antiquated belief that having a man fixes everything, perpetuated by women’s magazines and patriarchal beauty standards. That being said, I found it terribly funny. Bridget Jones (Renee Zellweger) represents a demographic of single women in their thirties, and admittedly, her natural state of being frazzled repeatedly lands her in some hilarious situations. On the flipside of this tragic selfhood she does teach the audience not to fall for the Daniel Cleaver (Hugh Grant) character, with the cheeky smile that hides his manipulative nature, and that the Mark Darcy (Colin Firth) character will love you for who you truly are.
Number of rewatches: 2
2. Ten Things I Hate About You (Junger, 1999)
Another Shakespeare adaptation, this film’s rendition of Taming of the Shrew is a hallmark of likeable, strong, female protagonists and genuine ‘enemies-to-lovers’. Kat Stratford (Julia Stiles) is opinionated, beautiful, clever, and no man’s peace. Her sister, cute, bubbly and popular, is her polar opposite, and though Kat’s feminism is somewhat mocked by the other characters, the film shows us that femininity is not uniform. Kat’s aura of coolness, from her “tempestuous” personality, to her taste for rock music and Sylvia Plath has me hooked from the start. It also helps that Heath Ledger is very nice to look at.
Number of rewatches: 2
Honorable mention: Legally Blonde (Luketic, 2001)
Legally Blonde is one of my holy-grail films, and, according to the internet, *technically* a rom com. However, I feel that to place it in the rom com genre would be to reduce the clever Elle Woods (Reese Whitherspoon) to the object of a sub-plot romance when her achievements and resilient attitude are what should take center stage. I would however, like to point out, that she displays the best characteristics for a rom com protagonist. When her friends and parents are skeptical of her goals, she doesn’t shut them out, choosing instead to graciously prove them wrong. While her new classmates are initially cruel to her the only person she ever outwardly insults is Warner (Matthew Davis) because he betrayed her. To the rest she is only kind, even befriending Vivian (Selma Blair) when she opens up to her. Though she is the spitting image of a privileged young woman, she never acts selfish or spoiled, forcing the audience to instead focus on what she can accomplish, and she does it all without ever losing her sunny, pink personality. If I were to call this film a rom com, that is the kind of protagonist I would find a delight to watch.
Number of rewatches: ?
1.Clueless (Heckerling, 1995)
Honestly, I think I would watch this film for that dream closet alone.
From the iconic outfits, to the slang I can still barely understand, to Brittany Murphy’s charming accent as Tai, to everything about Paul Rudd in the 90s, this film has everything that always has me coming back for the rewatch. Now, Cher (Alicia Silverstone) calling Tai her ‘project’ and attempting to change her for entertainment, while it had its humorous qualities, also had me raising a brow. While she starts the narrative with a self-confidence I would celebrate, this is not generally behavior I would endorse, even if she had the best intentions. However, I do think that it is through the development of this friendship that Cher is able to undergo her own character development, when Tai begins to reflect all the worst parts of her. When she has time to contemplate this is when she becomes self-aware enough to put those around her before herself.
Number of rewatches: 4
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