Valentine’s day is right around the corner, and there’s nothing better than a good romantic comedy flick to get someone in the mood for the holiday! However, there are so many movies to choose from, and if you’re like me you only want to watch the best.
In this article, we will review the best rom-coms from the late 1990s and early 2000s to get you in the mood for valentines day.
10 Things I Hate About You
Released in 1999, 10 Things I Hate About You is a cult classic. The movie has a large and talented cast, starring Julia Stiles as Katrina “Kat” Stratford, Heath Ledger as Patrick Verona, Joseph Gordon-Levitt as Cameron James, Larisa Oleynik as Bianca Stratford, Andrew Keegan as Joey Donner, and David Krumholtz as Michael, to name a few.
The movie mainly focuses on Kat Stratford, an independent, witty, and abrasive girl. Due to her nature, she doesn’t attract many boys. Bianca Stratford is the polar opposite of her sister. She’s conceited, bratty, and a little shallow. Bianca really wants to date, but their father is so worried about teen pregnancy that he won’t allow either of them to date until they graduate. In the midst of frustration, Walter allows his daughter to date under one condition— Bianca may get a boyfriend only when Kat gets one.
But how in the world would they be able to get Kat to date anyone? In an effort to get someone to ask Kat out a plan is hatched and chaos and drama ensues.
The chemistry between the two main couples is so sweet that you are left squealing at your screen. But, of course, with every good rom-com always comes drama! Even though I absolutely loved how the intrigue unfolded, I still got a little frustrated towards the end because of all the arguments and misunderstandings. However, the resolution makes it all worth it.
Even though all of the main characters have flaws, they are all still very easy to root for. The character development that the main characters go through is so satisfying to watch, especially Patrick and Bianca’s character arcs.
The film is based off of William Shakespeare’s comedy The Taming of the Shrew, which, I believe, is quite apparent when you watch it because of all the drama that happens and how the events play out.
This movie is now cemented in pop culture, having the most recognizable scenes including Patrick singing “Can’t Take My Eyes Off of You” and Kat reading her poem at the end, just to name a few.
Out of this entire list, if I had to recommend you only one movie to watch, it would have to be 10 Things I Hate About You.
50 First Dates
Released in 2004, 50 First Dates is known for its amazing performances from Adam Sandler and Drew Barrymore, who make a perfect pair for the film. The movie has a very interesting and engaging plot, and constantly leaves you wondering what is going to happen next.
Dr. Henry Roth, portrayed by Sandler, is a marine veterinarian at Sea Life Park, Hawai’i. He is characterized by his womanizer tendencies, going after tourists to avoid having to commit to a relationship. One day, he encounters an art teacher named Lucy, played by Barrymore, making architectural art with her waffles in a cafe. Henry decides to make it his goal to make Lucy fall in love with him. However, it is quickly discovered that Lucy has short-term memory loss, and is incapable of remembering anything that happened the day prior.
After finding out about this, Henry is determined to do anything in his power to be able to encounter her again for the “first time,” no matter how ridiculous and absurd his plans end up being.
Despite the very silly tone, the movie is surprisingly very bittersweet, and I definitely teared up at the ending. The filmmakers knew exactly how to frame the mood and tone. My favorite parts of the movie were when they really honed in on the silliness. The film was serious when necessary, but still managed to remain lighthearted and fun.
This movie was the second out of three times Drew Barrymore and Adam Sandler partnered up for a film, and I personally think this is the best movie they are in together. I loved everything about this movie— the plot, the characters, the jokes—it was all amazing. This movie will make you believe in soulmates again!
13 Going on 30
Released in 2004, 13 Going on 30 has solidified its spot on the pop culture podium, and contains one of Jennifer Garner’s and Mark Ruffalo’s most iconic performances. The movie has one of the more unique concepts I’ve seen for a rom-com, which gives it a neat edge that other films in the genre often don’t have.
The movie stars Jenna Rink, a nerdy, sweet thirteen-year-old girl. Matty Flamhalf, Jenna’s next-door neighbor and best friend, is secretly in love with her.
Eager to become one of the popular girls, she persuades the Six Chicks, her school’s ruling clique led by “Tom-Tom,” to attend her birthday party by doing their homework for them. When the Six Chicks trick and humiliate Jenna during her party, she wishes that she could be “thirty, flirty, and thriving.” The next morning, Jenna awakens as an adult in a luxurious Fifth Avenue apartment in 2004, dating a young man she does not recognize and with no memory of the previous seventeen years. With the mind of a naive girl and the appearance of a mature woman, Jenna struggles to navigate adult life, unsure of how to get things back to the way they were.
After Jenna hears about all of the terrible things that the older version of her has done, she tries to make amends and reconnect with the loved ones her older self became estranged from, including Matty.
13 Going on 30 is the perfect feel-good movie that amazingly captures what it’s like to be an adult who is still a kid at heart. The relationship between Jenna and Matty is the perfect example of that slow-burn, childhood friends to lovers trope. The couple shows how important it is to keep the people who truly care about you close.
It also contains one of the most recognizable, vibrant dresses of the early 2000s from the com era, perfectly encapsulating the Y2K, fun, and flirty vibe the movie represents. Not only that, but the dress is paired with the most iconic dance scene in the movie.
Overall, the movie gives a wonderful message that getting older doesn’t mean that you have to lose your joy and whimsy. It also shows that everyone has a chance to turn their life around for the better. If you want to have a good laugh—and maybe a good cry, too— then you need to see this film!
How to Lose a Guy 10 Days
Released in 2003, How to Lose a Guy in 10 Days is one of, if not the most well-known romantic comedy movies. Starring Kate Hudson as Andie Anderson and Matthew McConaughey as Benjamin Barry, this film really puts the com part in rom-coms! It is truly one of the funniest movies of this genre I have ever seen.
The main character, New Yorker Andie Anderson, is a columnist for the women’s magazine ‘Composure’. Andie longs to start writing more serious articles, however, her skills are underestimated by her editor Lana because she is solidified as the company’s “How-To” girl.
Meanwhile, her friend Michelle struggles with keeping relationships, and when she experiences yet another break up, Andie gets inspired to write a new “How-To” article that just might get Lana to take her seriously—“How to Lose a Guy in 10 Days.” Her goal is to show Michelle the “classic mistakes” women make in relationships that can drive a guy away in ten days. Andie and her coworkers find the perfect test subject for her article at a bar— Benjamin Barry. Little does Andie know that Ben has his own ulterior motives going into this.
If you ever heard of the term “ragebait,” then you would have no issue connecting it to the whole premise of the film. The movie encapsulates the “annoying clingy girlfriend” trope in a hilarious way. There was never a moment when I wasn’t giggling or snickering at my screen while watching it. The filmmakers never take themselves too seriously; they know what they are trying to accomplish and stick with it.
The movie also has a great soundtrack, featuring “You’re So Vain” by Carly Simon and a rom-com classic, “Kiss Me” by Sixpence None the Richer. The filmmakers couldn’t have picked a better score, as the songs match the vibe of the movie perfectly. How to Lose a Guy in 10 Days is another rom com with an iconic dress. The gorgeous yellow gown that Andie is featured wearing in the promotional poster was created by Carolina Herrera with the film’s costume designer.
If you like light-hearted, more comedic movies, then How to Lose a Guy in 10 Days is a must watch for you!
Whether you are a hopeless romantic, enjoy a good laugh, or just want to watch an entertaining film, these movies are some of the best rom-coms out there. So grab your popcorn, cozy up, and give these films a watch!
