The 2000s were an interesting decade for movies. As we entered The New Millennium, the film industry revitalized its content to appeal to a modern world. Movie-going audiences saw the resurgence of fantasy films in the 2000s thanks to Harry Potter and The Lord of The Rings, superhero films were beginning to grow in popularity, and animation entered the digital world.
One thing that did stay constant in the 2000s is that chick flicks continued to emphasize the importance of friendship and love. From modern fairy tales to films that would later become full-blown feminist icons, the 2000's really pushed a brand new take on the chick flick while also retaining all the parts audiences loved best from the subgenre's previous decades.
Updated on May 2nd, 2021 by Kristen Palamara: Romantic comedies are a beloved genre for many people and many refer to these movies, usually lovingly, as chick flicks. The movies are always light-hearted but can have seriously dramatic moments as well or an overall larger feminist message to its plot that is thinly veiled beneath the typical rom-com format. There are love stories and dramatic gestures of affection throughout these nostalgic 2000s chick flicks that any rom-com fan would love to watch and rewatch over and over again.
15 HONORABLE MENTION: A Cinderella Story (2004) - 5.9
Inspired by the classic fairy tale, A Cinderella Story modernized the classic fairytale by centering on Sam (Hilary Duff), an outcast student who starts a pen pal relationship with one of the most popular boys at her high school despite her knowledge.
While not the biggest with either critics or an overwhelming majority of audiences, A Cinderella Story was a big commercial success and went on to inspire four other modernized takes of Cinderella over the next several years. Though it received negative reviews at its release, the film has since been considered a cult classic and a much-watch teen romance.
14 Sweet Home Alabama (2002) 6.2
Sweet Home Alabama stars Reese Witherspoon as a New York fashion designer and socialite who has to return home to Alabama to get her husband (Josh Lucas) to finalize their divorce papers as she's about to get married.
She, of course, gets pulled back into her old life that she thought she left behind for good as she visits her family and old friends, and rekindles a relationship with her ex.
13 Just Friends (2005) 6.2
Just Friends is another movie that sees its main character return home after leaving behind a difficult childhood he wanted to run away from. Ryan Reynolds stars in this rom-com as a successful music manager who is forced to spend Christmas at home.
He rekindles a relationship with the girl he had a crush on in school and decides to make her fall in love with him as a sort of payback for him feeling wronged by her when they were best friends in high school and he was in love with her. The basis of the plot is a bit outdated, but it's still a fun watch and the holiday setting makes it a fun watch in December.
12 Miss Congeniality (2000) - 6.2
The Sandra Bullock-led Miss Congeniality kicked off the 2000's and certainly set the standard high for chick films of the time. The film follows Gracie Hart (Bullock), an FBI agent who goes undercover in the Miss United States beauty pageant in order to stop a terrorist threat placed on the pageant.
Miss Congeniality was not only commercially successful but also critically as well, helping Bullock earn a Golden Globe nomination for Best Actress in a Motion Picture Comedy or Musical, though she lost to Renée Zellweger for Nurse Betty. The movie got a sequel -- Miss Congeniality: Armed & Fabulous -- that also became a cult hit despite some rather negative reviews.
11 Uptown Girls (2003) - 6.2
Uptown Girls centers on Molly Gunn (Brittany Murphy) a wealthy young woman who has her inherited fortune stolen from her and ends up taking a job as a nanny to make ends meet. In a twist of events, Molly ends up learning how to be an adult from Ray (Dakota Fanning), the young girl she's babysitting.
Despite being a commercial success, the film was not well received by critics, who felt Molly and Ray were both too insufferable to care about. In light of Murphy's untimely passing, Uptown Girls has seen a resurgence in appreciation especially from Fanning, who's been openly grateful for her time on the film.
10 13 Going On 30 (2004) - 6.2
Often compared to Tom Hanks' Big, this Jennifer Garner vehicle sees her portray Jenna, an awkward thirteen-year-old girl who gets her wish and becomes a 30-year-old working woman overnight. While at first, it seems like adult Jenna is living her teenage self's dream, she quickly realizes that adulthood isn't all it's cracked out to be.
13 Going On 30 was well-received across the board, earning $97.7 million against a $37 million budget. In addition, the movie became one of 2004's best-selling and most-rented DVDs. The movie earned praise for its message about how young girls should handle insecurities, and what it means to be true to one's self.
9 She's The Man (2006) 6.3
She's the Man is a fun adaptation of Shakespeare's Twelfth Night that sees Viola (Amanda Bynes) take her twin brother's spot at a boarding school so she can join the men's soccer team and show her old school that she's just as good as the boys.
Viola has to navigate her new social life and try her best to focus on soccer as well, which proves to be difficult. It's a hilarious and nostalgic movie for anyone who grew up with it in the 2000s.
8 Legally Blonde (2001) - 6.3
Arguably one of the most iconic early 2000s chick flicks and one of Reese Witherspoon's best films is none other than Legally Blonde. Witherspoon plays Elle Woods, a bubbly woman who lives for everything fashion and beauty. After her longtime boyfriend dumps her, she decides to go to Harvard Law School in the hopes of winning him back.
While the film's premise might seem anti-feminist at first glance due to it seeming to perpetuate some shallow stereotypes of women, Legally Blonde actually has an extremely feminist message as Elle rises above all the doubts and hate she receives in order to earn her law degree. The film was a huge success and even earned two Golden Globe nominations, spawning sequels and spin-offs that are better left ignored.
7 The Princess Diaries (2001) - 6.4
Directed by the legendary Garry Marshall and based on a book by Meg Cabot, The Princess Diaries followed Mia Thermopolis, a young teenager who has her world turned upside down when her estranged grandmother comes into her life to inform her that she is actually a princess.
The Princess Diaries marked Anne Hathaway's film debut and is also credited for revitalizing Julie Andrew's acting career. In addition, the film went on to become a major hit, earning a sequel and with rumors swirling around a potential third entry.
6 Mamma Mia! (2008) - 6.4
Audiences got a taste of a cinematic jukebox musical when Mamma Mia! hit theaters. The film starred Meryl Streep as Donna and Amanda Seyfried as Sophie, a mother-daughter duo who are planning the latter's wedding. With the help of every classic ABBA song known to civilization, Mamma Mia! follows the women as they plan the big day and deal with the aftermath of Sophie inviting all three of her possible fathers (also Donna's ex-flames) to the wedding.
Mamma Mia! was insanely popular with audiences, earning a whopping $615.7 million at the box office against a $52 million budget. The film went on to become the fifth highest-grossing film of 2008 and even got a sequel in Mamma Mia! Here We Go Again.
5 Nick And Nora's Infinite Playlist (2008) 6.6
Nick and Nora's Infinite Playlist is a lesser-known rom-com of the 2000s that stars Michael Cera as a heartbroken man who can't get over his ex-girlfriend and Kat Dennings as a new friend he meets out one night.
The two spend the movie searching for her friend and accidentally running into his ex as they have to decide what their adventure together means and what they want next in their relationship.
4 The Proposal (2009) - 6.7
Sandra Bullock once again finds herself on the list of best 2000s chick flicks with The Proposal. This time, Bullock plays Margaret Tate, an uppity Canadian book editor who claims she is engaged to her awkward American assistant Andrew (Ryan Reynolds) to avoid deportation following a violation regarding her American work visa. As expected, this leads to a hilarious romance.
Bullock and Reynolds's performance carried the film leading it to gross $317 million at the global box office. In addition, Bullock received a Golden Globe nomination for it but she lost to Meryl Streep for Julia & Julia. Helping this movie's case is the presence of none other than Betty White.
3 Mean Girls (2004) - 7.0
Arguably, Mean Girls is one of the most iconic teen films not just of the 2000s but of all time. The film stars Lindsey Lohan as Cady Heron, a teenager whose family has moved from Africa to the suburbs of Illinois. When Cady attends school for the first time she ends up befriending the popular clique "The Plastics," headed by the domineering Regina George (Rachel McAdams).
Mean Girls was inspired by a non-fiction self-help book and was written for the big screen by SNL alumni Tina Fey, who also stars in the film. This hilarious satire of the ups and downs of high school life and what growing up is like for teenage girls is now considered a bona fide classic. Mean Girls is so popular that it even got adapted into a Broadway musical.
2 Definitely, Maybe (2008) 7.1
Definitely, Maybe follows a father (Ryan Reynolds) telling his daughter (Abigail Breslin) the story of how he met her mother. He tells her about his life before he met her and highlights three women he met around the same time who impacted his life.
The movie switches between times as he builds a relationship with people in his past and the audience tries to guess which woman is her mother.
1 The Notebook (2004) - 7.8
Adapted from a Nicholas Sparks romance novel of the same name and arguably the most popular of the movies he inspired, The Notebook follows Ryan Gosling and Rachel McAdams as Noah and Allie, two young adults in love in the '40s. The film switches between the '40s and the 2000s, where an elderly man is telling the love story to an elderly woman in a nursing home.
The Notebook went on to gross $116.1 million against a $29 million budget and was nominated for several minor awards. The film is currently the fifteenth highest-grossing romantic drama of all time and remains one of the most beloved Sparks movies.
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