Everyone loves a rom-com. There's something about seeing two people fall in love on the screen that warms the heart, and having some laughs along the way makes it even better. Romcoms were a popular genre of the nineties and early aughts. These movies featured some of the most popular celebrities, from Jennifer Lopez to Matthew McConaughey to Hugh Grant.
However, not all romcoms are made equal. Some left audiences wanting more, and some had nonsensical plots, had bad writing, or lacked chemistry between the leads. Here is a list of the best and worst romcoms of the 2000s.
Best: 27 Dresses (2008)
This 2008 rom-com features Katherine Heigl as Jane, a woman who is quite literally always the bridesmaid. She's been in 27 weddings, but when her younger sister Tess begins dating and eventually becomes engaged to the man she loves, Jane is devastated. Add to that a reporter who becomes interested in covering Jane's story, and its no wonder this film is considered a classic.
Heigl's chemistry with each of the characters in her circle -- her sister Tess (Malin Akerman), her best friend Casey (Judy Greer), her love interest George (Edward Burns), and the reporter Kevin (James Marsden) -- adds to the film's likeability. Overall, the concept is relatable and in the end, you root for Jane to find her own happiness.
Worst: The Sweetest Thing (2002)
The Sweetest Thing is as much a raunchy road trip as it is a rom-com. Cameron Diaz plays Christina, who's wholly disinterested in finding the love of her life until she meets a man named Peter at a club. However, when Peter leaves to go to his brother's wedding, Christina and her best friend Courtney (Christina Applegate) embark on a road trip to find him.
What follows is a series of inane gags and attempts at raunchiness that tries to top male-dominated comedies. Additionally, the plot is razor-thin -- Christina decides to crash Peter's brother's wedding after meeting him once. With all of this plus a weird scene involving an unfortunate piercing, it's no wonder critics generally didn't like the film.
Best: Love and Basketball (2000)
This film follows Sanaa Lathan and Omar Epps as childhood friends Monica and Quincy. They share a love for basketball and eventually each other, though their relationship is strained by family issues and the pressure of college. The pair reunites years later, and audiences can't help but cheer for the pair as they get back together.
This movie is as much about love as it is the struggle of pursuing dreams and trying to have it all. The chemistry between Epps and Lathan is palpable and it is a classic rom-com with a mostly black cast.
Worst: Sweet Home Alabama (2002)
This film features a star-studded cast of Reese Witherspoon, Patrick Dempsey, and Josh Lucas. Witherspoon plays a woman named Melanie who returns home to Alabama after becoming engaged to her boyfriend, Andrew (Dempsey). Melanie's visit is two-fold -- she plans to announce her engagement to her family and divorce her first husband, Jake (Josh Lucas).
While at home, Melanie reconnects with old friends and with Jake, and she must decide which man she really loves. The story's plot -- successful person returns home and learns the true meaning of life -- has been done many times before. Despite Witherspoon's energy and chemistry with Lucas, the plot and the writing leave a lot to be desired.
Best: My Big Fat Greek Wedding (2002)
This film is the quintessential ugly duckling turned swan film. It follows Toula (Nia Vardalos), a waitress at her parent's Greek restaurant, Dancing Zorbas. After she meets a man named Ian who she is instantly attracted to, Toula decides to go back to school.
Growing more confident, she changes her wardrobe, starts wearing makeup, and convinces her parent to let her work as a travel agent at her aunt's company. Ian and Toula meet again and begin a relationship. My Big Fat Greek Wedding is a feel-good film that's as much about learning to love yourself and accept one's heritage as it is about falling in love.
Worst: Serving Sara (2002)
This 2002 film features Matthew Perry as a process server named Joe who goes to serve divorce papers to a woman named Sara played by Elizabeth Hurley. She convinces him to serve her ex-husband instead, and the pair hatch a plan to do so.
The film received a ton of negative reviews, with many of them blaming the film's writing, an attempt at conventional comedic gags, and a flimsy plot. Additionally, some reviewers found the chemistry between Perry and Hurley to be almost non-existent, with a New York Times review saying that the pair "barely seem to notice each other even when they're halfheartedly sparring."
Best: The Princess Diaries (2001)
The Princess Diaries is every teen girl's dream come true. The Gary Marshall film features Anne Hathaway in her first role as Mia, a shy and nerdy teen who finds out that she's the princess of a European country called Genovia.
After this, Mia must navigate jealous classmates, a popular boy whose attention seems too good to be true, and another Genovian family who wants to take the throne from her. This cute coming-of-age film is made for the underdogs who dream of showing up the popular kids. As always, Hathaway is electric as Mia even when she's in a bad wig and sporting coke-bottle glasses.
Worst: Shallow Hall (2001)
Shallow Hal features Jack Black as Hal, a shallow man whose obsession with women's appearance hinders his ability to see their inner beauty. He is hypnotized by Tony Robbins and promptly meats a woman named Rosemary (played by Gwenyth Paltrow), who is the daughter of Hal's employer and a plus-sized woman. However, because of Robbins hypnosis, Hal sees her as a lithe blonde.
For a film that tries to combat conventual beauty standards for women, having Hal and Rosemary end up together, in the end, sort of undoes what the directors were attempting to do, because who wants to be with someone that once felt they weren't good enough for them?
Best: The Holiday (2006)
This film features two romantic storylines after two women swap houses for a vacation. Film trailer maker Amanda (Cameron Diaz) decides to take a vacation after discovering her boyfriend has cheated on her. Journalist Iris (Kate Winslet) decides to leave her small English village after she finds out the man she's in love with is marrying someone else.
In each other's stomping grounds, Amanda meets and begins a romance with Iris' brother Graham (Jude Law) and Iris meets Miles (Jack Black) a friend of Amanda's. The Holiday gives viewers both romance and solid character development, as each woman overcomes their biggest hangups. Both sets of couples have incredible chemistry, especially Winslet and Black who share a very touching moment in a Blockbuster.
Worst: 40 Days and 40 Nights (2002)
This film features Josh Hartnett at the height of his status as Hollywood heartthrob. In 40 Days And 40 Nights, Hartnett plays a man named Matt who decides to abstain from sex for Lent in an attempt to overcome his latent feelings for his ex, Nicole. However, Matt didn't count on his friends and coworkers making a bet for how long he could remain celibate, or the fact that he'd meet and fall in love with another woman.
Apart from the problematic claim the film makes that men are obsessed with sex, it also includes one of the most awkward sex scenes of the new Millenium and attempts to use rape as a plot device. Though the film has a few funny moments, it isn't a must-watch.