Movies are made to tell a story. Some stories are scary, keep you on edge, while others may inspire you, bring hope, or make you laugh. Chick-flick movies are one of many genres of film that people often flock to. Perhaps it is the promise of a heart-wrenching, inspiring, tear-jerking story of perseverance. Maybe it is the chance for a happy ending when we know life doesn’t always provide those. Sometimes we cling to the idea of a great romance or seeing a relatable character overcome a hardship. Other times we cling to the movies that showcase great friendships that we wish we had or remind us of our best friends, either way, we love chick-flicks, and some of the best ones were created in the 1990s and 2000s. Here are 10 Chick-flick movies from the 1990s and 2000s that we still love.
1. How to Lose a Guy in 10 Days
If you love romantic comedy movies, you will like How to Lose a Guy in 10 Days starring Kate Hudson and Matthew McConaughey. How to Lose a Guy in 10 Days is a delightful and fun romantic comedy released in 2003. Hudson plays Andie Anderson, a writer for a magazine. She is tired of writing the same humdrum articles, and in a last-minute idea, she decides to write a how-to article with a twist. Andie decides to date a man and does all the things that drive men away when dating them. In a funny twist of events, Benjamin Barry (McConaughey) is in advertising and bets his co-workers that he can make any woman fall in love with him. The woman he works worth knows all about Andie’s article and pushes Ben to make Andie fall in love with him without him knowing about Andie’s true intentions. Andie does hilarious actions to ward off Ben, but Ben is determined to win the bet amongst his co-workers. While this couple maneuvers and tries to stay afloat for the ten days, an unexpected romance blossoms leaving the viewers with a sense of satisfaction and just enough sweetness to satisfy any romance lover.
2. 13 Going on 30
Starring Jennifer Garner, Mark Ruffalo, Crista B. Allen, and Judy Greer, this story of a young girl named Jenna Rink (Crista B. Allen) who wishes to be 30 years old instead of 13. She wants to be a grown-up with a woman’s body, an amazing job, and life. She believes what she reads in her magazine is who she needs to be happy. Jenna’s best friend, Matt, creates a dollhouse for her with wishing dust. In the midst of a humiliating party, Jenna makes a wish that she was “thirty, flirting, and thriving,” according to the magazine she read. Shortly after her wish, Jenna wakes up as an adult version of herself (Garner) and realizes she is now 30, working for the magazine of her dreams with mean girl Lucy (Greer). Jenna finds out she is no longer friends with Matt and, in fact, became a bit of a mean girl in school and dropped him for her newfound popularity. While Jenna tries to juggle her new life, she attempts to mend her relationship with her former bestie but finds herself in love with him. Unfortunately, Matt is set to be wed soon, and Jenna realizes that she has always taken Matt for granted. Jenna must try to make things right in many aspects of her life and realize that not all you wish is the best for you. Sometimes, what you have is all you need. This is just one of many movies Ruffalo did in the 2000s with romance, embracing the moment, and being content with oneself.
3. 10 Things I Hate About You
10 Things I Hate About You is one of Heath Ledger’s most memorable movies. Heath Ledger and Julia Stiles star in a modernized retelling of William Shakespeares Taming Of The Shrew. The Film is classified as a romantic comedy, and we absolutely love it! Ledger’s bad boy act proves to be only his exterior as Kat makes him fall in love with her based on her witty and, at times, snarky and hardheaded mentality. Kat comes off as a male-hating female, but in reality, she has been hurt in the past and is more cautious of the males’ intentions around her and her sister Bianca. Bianca is told she cannot date unless her older sister does, so she gets Cameron, a young man completely infatuated with Bianca, to find someone to take her out. Low and behold, it is Ledger’s character, Patrick. Bianca does not initially see Cameron as a potential prospect and wants to date the most popular male in school, Joey. Bianca soon realizes he is not all he is cracked up to be. In a twist of fate, Cameron and Bianca end up together, but Kat finds herself in a less-than-stellar situation when she realizes she was taken out by Patrick because he was paid. Much to Patrick’s own surprise, he has fallen in love with Kat and does not care about the payment any longer. 10 Things I hate About You takes you on a roller coaster ride of emotions but is a fun, refreshing version of a chick-flick as Kat is a take-no-crap female lead.
4. She’s All That
She’s All That stars Freddie Prinze Jr. and Rachel Leigh Cook. Rachel Leigh Cook plays Laney Boggs, an artistic and quiet high school senior who is overlooked and hangs out with her best friend Jesse in between her work and creating art. Freddie Prinze Jr. is the all-around popular big man on campus Zack Siler. Zacks’s popular girlfriend, Taylor Vaughan (Jodi Lyn O’ Keefe), takes off with a reality tv star Brock Hudson (Matthew Lillard) and dumps Siler after Spring break. Zacks buddy Dean Sampson (Paul Walker) bets Zack that he cannot turn any girl into Prom Queen. Zack takes the bet and is given Laney as the girl he must make into Prom Queen. Zack enlists his sister Mackenzie (Anna Paquin) to help makeover Laney for a party. Zack does all he can to show off Laney, but she gets humiliated by Zacks ex-girlfriend Taylor in the midst of it. Laney finds out from Dean that it was all a bet and refuses to stay with Zack. Unfortunately for Zack, he has fallen in love with Laney. She’s All That demonstrates that love can be found in unlikely places, with people we least expect, but we could ruin something great if we are not honest and forthcoming with our intentions, but hey, there’s always a chance for redemption if you are genuine about your feelings.
5. Bride Wars
Bride Wars stars Kate Hudson and Anne Hathaway as best friends Liv and Emma. The two women are nearly inseparable since they were kids, and they share a mutual dream of being married at the Plaza one day. Both Liv and Emma end up engaged at the same time and decide to go to plan their dream weddings. Unfortunately, Marion double books their weddings for the same day, and there are no other openings for the Plaza. The two women end up head to head trying to outdo each other’s weddings and losing sight of their amazing friendship in an all-out war with their weddings. Each woman attempts to sabotage the other’s wedding in hopes that their mutual guests will attend their weddings and that they will have a better wedding. In the end, Emma realizes she cannot marry her fiance as he wants nothing more than to change who she is and wants her to be the person she was many years before. Emma ends up with Livs brother, who saw her and loved her for who he was all along. While the movie has hilarious moments and does have romance and is about weddings, it is more about friendship and remaining true to who you are to preserve your happiness.
6. The Wedding Planner
The Wedding Planner stars Jennifer Lopez and Matthew McConaughey in this feel-good witty comedy. Mary (Lopez) is a lonely wedding planner who plans every detail down to a beautiful pep talk for brides who have cold feet on their special day. She foresees potential disasters or moments that can ruin or cause a less-than-stellar wedding. Mary is enlisted to help plan Fran and Steve’s wedding, but there is one little problem. Mary was saved by Steve and taken care of in a children’s hospital after being hit by a dumpster. Mary had no idea that Steve was set to be married to Fran and now has to ignore her attraction to him whilst planning their wedding. While it sounds easy, it grows increasingly obvious that Fran and Steve are not meant to be while Steve’s and Mary’s feelings grow. Eventually, Steve decides to call off the wedding to Fran and opts to go with his feelings for Mary instead.
7. My Best Friends Wedding
This 1997 film starring Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett is all about true love, friendship, and learning to let go for others’ growth. Julia Roberts plays Julianne Potter, a woman who made a pact with her best friend Michael years prior that if they were both not married by the time they were 28, they would marry each other. Julianne receives a phone call from Michael and begins to wonder if it is about their pact. However, Julianne discovers that Michael is getting married to a young woman named Kimberly Wallace (Diaz), and Julianne is requested to come to the wedding. When Julianne sees Michael and Kimberly, she grows increasingly possessive and jealous of their relationship. Julianne decides to tell Michael that she has always loved him and intends to steal him away from Kimberly and sabotage their wedding. In the midst of her crazy scheme, she employs her other close friend, George, to help her and pose as her fiancé. Overall, Julianne must confess her true intentions and come to the realization that she will always remain friends with Michael and have a bond with him, but sometimes it is best to let your best friend go and live their best life with your support. This is one of Roberts’s best movies with a relatable storyline that most of us can appreciate.
8. Now & Then
Not all chick flicks are created equally. This one is tiny to do with romance and is all about friendship and coming of age. This film showcases great friendships that withstand the years and bring together friends for an important and life-changing event for one of the girls. A story filled with drama, laughter, a few tears, and of course, loyalty. Now & Then has an all-star cast starring Christina Ricci, Thora Birch, Gaby Hoffmann, Ashley Aston Moore, Demi Moore, Rosie O’ Donnell, Rita Wilson, Melanie Griffith, and Devon Sawa. The Movie has loads of stars, but the story is that of four girls who each have a very different life or family but form the strongest friendship and bond. The movie follows the girls in the summer of 1970. As you follow the girls growing up and coming of age and their self-discovery, the audience is brought to the present day to see the girls as adults, and one is at the end of her pregnancy. While each of the women has different lives, jobs, and lifestyles, their bond is still undeniably strong, and they come together for their friends’ first pregnancy and delivery, all while reminiscing on old times. Written by one of the greatest storytellers, I. Marlene King brings to life relatable characters that the audience will laugh and cry with over and over again.
9. Never Been Kissed
In the 1999 film Never Been Kissed stars, Drew Barrymore, a copywriter for the Chicago Sun-Times, goes undercover as a high school senior to find a gripping story. Instead, she discovers what it is like to be a student today versus when she was in school. Unfortunately, she falls for an English teacher who would seem inappropriate based on her assumed age. Still, because she is an adult, she finds it difficult to separate how she feels versus her job to find a hard-hitting story. Josie (Barrymore) ends up writing about her time as a student and falling in love with the teacher. She writes a compelling story about never being kissed and asks for him to meet her and give her her first kiss. Because the story is so compelling, news media and cameramen show up to cover the event. Josie Stands center field, starring into the crowd of former students, family, and reporters, grows increasingly sad as she believes the man of her dreams will not show up. Of course, in true chick flick format, Josie and the crowd are in for a great surprise.
10. The Wedding Singer
Drew Barrymore and Adam Sandler have great chemistry in this film about non-other than a wedding singer! Sandler plays a wedding singer trying his hardest to bring smiles and happiness to others while singing at their weddings. Julia (Barrymore) is a waitress and bother Robbie (Sandler), and she is engaged to other people. However, Julia’s fiance is not such a great guy. He is a womanizer and lies about his true intentions. When Robbie discovers Julia’s fiance is a jerk, he looks out for her, but he, of course, has his own relationship to deal with. Robbie’s fiance is also not the greatest apple in the bunch. She is quite pushy and rude, she doesn’t let him have a say in most things, and of course, she ends up breaking his heart. Eventually, the two realize they’ve chosen the wrong partners initially and find that they are better off together. Sandler and Barrymore come together for other romantic comedy movies, but The Wedding Singer is a rom-com that does not go over the top in cheesiness, and we love it!
There are many movies from the ’90s, and 2000’s that we love and will watch on repeat. Let us know if you love this list by sharing a favorite quote from one of the movies you love from above!
I am a writer, artist, mother, and wife. I am from California but currently reside in Arizona. I have a BA in English with a concentration in writing. I have a certificate in SEO through Universal Class. I love music, art, writing, pop culture, gaming, anime, and Disney.