The 15 Best Romantic Comedies from the Early 2000s

The ’90s were a simpler time for romantic comedies. Meg Ryan, Julia RobertsPlease see the following: Sandra Bullock ruled the box office with movies that had them falling for men who were dabbling in a bit of harmless catfishing (1998’s You’ve Got Mail), hiring them as an escort (1990’s Pretty Woman), or were stuck in a coma (1995’s You were sleeping). Which one of us is right?

In the beginning of 2000s the romcom market was growing rapidly, but it wasn’t as popular as the established and trusted. Sally and Harry: When Harry met Sally model—boy meets girl, girl hates boy, boy and girl become friends and eventually fall in love—felt a little been there, done that. “The 2000s were a turning point for the modern Hollywood rom-com,” says Scott Meslow, whose recently released book, Hollywood with Love: The Rise, Fall and Rise (and Again) of Romantic Comedy, tracks the crowd-pleasing, but oft-maligned genre’s ups and downs over the past three decades. “That’s when things got a little more contrived and cartoonish.”
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Meslow says that director was the rom-com which set the tone in the early aughts. Nancy MeyersThis is what women want. The 2000 film starred Mel Gibson as a chauvinistic ad exec who magically acquires the ability to read women’s minds. Though it is far from Meslow’s favorite rom-com, he argues that What women want marked a watershed moment in Hollywood in which a couple simply falling in love didn’t cut it anymore. Rom-coms of the early 2000s needed some kind of zany twist, like a female protagonist who is afflicted with short-term memory loss (2004’s 50 First Dates) or is a ghost (2005’s Heaven is just like it).

You can be sure Hollywood, Love and Other MoviesMeslow created a test for determining if a film was true romantic comedies. The film may be a romantic comedy if the answer is “no”. This means that you can still enjoy turn-of the century classics like Prada is the Devil’s Clothes13, Going on 30 And Legally BlondeYou won’t make it.

It is the rom-coms that understand that, no matter how complex the plot might be, it must be relatable. You must want the audience to root for the happy ending. “In some ways, making a fun zippy rom-com is maybe the hardest kind of movie to make,” Meslow says. “It’s very hard to disguise if you don’t have what you need.”

Using Meslow’s guidelines for what constitutes a romantic comedy, we’ve put together a list of the 15 rom-coms that we think still stand out two decades later. From J.Lo’s rom-com debut to Judd Apatow’s most endearing comedy, here are the early 2000s movies we think combine romance and comedy the best:

Bridget Jones’s Diary (2001)

The film based on Helen Fielding’s 1996 novel, which, in turn, was inspired by Jane Austen’s Pride and Prejudice This compassionate depiction of singledom is offered. This is a romantic comedy. Renée Zellweger’s BridgetThe one thing she fears the most is turning into a spinster, whose best relationship is with wine. When she meets Daniel Plainview, her boss Daniel Plainview, she is forced to enter a relationship with him.Hugh Grant) and snobbish divorcé Mark Darcy (Colin Firth), she begins to realize that she’s worthy of love Just as she is.

It’s available on HBO Max

Amélie (2001)

Audrey Tautou’s manic pixie dream haircut and her traveling gnomes might be a little too twee for some, but at the heart of this whimsical French film is a lonely young woman trying to connect with the world around her. On a quest for kindness to help others, Amelie finds herself in a game of cat-and mouse with Nino Kassovitz (Mathieu). The question of whether Amélie will finally take a chance on love is the real will-they-or-won’t-they of the film.

Inaccessible to stream

Kissing Jessica Stein (2001)

It queer rom-comHollywood is not used to this kind of thing. Jennifer Westerfeldt stars as the woman in this movie, who is exploring her sexuality at her Jewish family’s request. Not everyone is a fan of the film’s ending, which we won’t spoil here, but it shows that when it comes to matters of the heart, it’s often about the journey not the destination.

Amazon Prime Video Rentable

Brown Sugar (2002)

It is important to start early Brown Sugar, named for D’Angelo’s debut album released seven years earlier, was labeled “hip-hop Sally and Harry: When Harry met Sally.” Chalk that lazy comparison up to the genre’s overall lack of diversity. The Rick Famuyiwa directed film has an incredible soundtrack and features a number of legendary rap artists. It is, in fact, a refreshing update on the friend-to-lovers trope. Love & Basketball’s Sanaa Lathan The Best Man’s Taye Diggs‘ crackling chemistry as two childhood friends who are too scared to admit they want to be more.

It’s available on HBO Max

My Big Fat Greek Wedding (2002)

Whether or not your dad uses Windex as a cure-all, it’s such hilarious details in Nia Vardalos’ fictional portrait of her real family that help this film feel universal. The movie’s success is due to her attention to these eccentric details. Highest-grossing Romantic Comedy until Crazy Rich AsiansIt broke the recordIn 2018. (My Big Fat Greek WeddingIt is still the top-grossing independent rom-com. She did so by bucking the studio’s notes that her movie needed a villain. Vardalos knew that there’s nothing more frightening than a lovingly overbearing family.

It’s available on HBO Max

Manhattan maid (2002)

Jennifer Lopez made her rom-com debut as a struggling single mom who falls for a high-profile guest (an American-accented Ralph Fiennes), who doesn’t realize she is the maid at the hotel where he’s staying. While the movie has its flaws, it’s J.Lo who transcends its faults. With each longing look, Jenny from the Block makes you believe that she’s a woman who is risking it all for love. Twenty years later, Lopez has solidified herself as, according to TIME’s film critic Stephanie Zacharek, the patron saint of the rom-com with her latest film, You can marry me, But Manhattan maidIt was clear, she was the leader of the genre.

It’s available on HBO Max

Punch-Drunk Love (2002)

Paul Thomas Anderson knew what he was doing when he hired Hollywood’s favorite leading man Adam SandlerHis quirky indie rom-com. This actor is well-known for his yelling and comedic performances in movies like Billy Madison And Happy Gilmore His impressive pipes are used to create a picture of a misanthrope finding happiness through an unlikely love connection. This sweet glimpse of Sandler’s crazy and sometimes foolish love showed that he had an actor’s side. It also proved that PTA was a talented rom-com writer.

It’s available on HBO Max

In 10 Days, How to Lose A Guy (2003)

Kate Hudson Matthew McConaughey’s performances in this harebrained movie are straight-up bonkers—and that’s a compliment. Andi Anderson (Hudson), a Journalist, wants to show that she is capable of getting a man to end their relationship in just two weeks. To do this, she will smother him with love plants and rat dogs. To prove that he is capable of making any woman fall for him, Ben Berry (McConaughey), a sex exec at McConaughey’s advertising agency, will endure Celine Dion concert and a vanity filled with tampons. When the pair stop acting completely insane and begin to be real, the audience is able to move from calling. “bulls–t, mama”The whole idea is to root for the two of them to succeed.

Peacock, watch it!

Something’s Gotta Give (2003)

Nancy Meyers movies are filled with stunning kitchen scenes, but the director has an uncanny ability to create characters that truly feel like they exist. It all starts with the script, and it continues through the casting. Diana Keaton is a successful playwright Erica Barry who has lost her love for the past two years. Harry Sanborn is her match.Jack Nicholson(a similarly successful entrepreneur, who is now dating his daughter. But after suffering a heart attack, he takes stock of his life and realizes dating twentysomethings isn’t as stimulating as he once thought. The two soon realize there is no expiration date on love—and audiences learned that sometimes Keanu Reeves isn’t “the one,” but a worthy runner-up.

You can watch it at Amazon Prime Video

50 First Dates (2004)

Six years ago, Adam Sandler sang of wanting to age with Drew BarrymoreIn The Wedding Singer he’s back pulling out all the romantic stops to help her remember they’re in love today knowing, due to her short term memory loss, she won’t remember him tomorrow. While we won’t defend the science here, the idea of someone committing so fully to performing such romantic acts is basically the dream of eternal love.

Amazon Prime Video – Rent It

The 40-Year Old Virgin (2005)

Judd Apatow’s film about Andy (Steve Carell), a shy guy who, four decades into his life, still hasn’t had sex yet was sold as a raunchy comedy for men. Much of the humor between Andy and his manchild friends doesn’t age well, but the love story between Carell and Catherine Keener is as charming as ever thanks to their commitment to the idea that there is more to love than sex.

It’s available on HBO Max

Something New (2006)

The moment Sanaa Lathan’s career-focused Kenya McQueen starts listing off what she’s looking for in a man: good teeth, college educated, and “not crazy,” you know she’s destined to fall for someone who’s all wrong for her. Brian Kelly, her white landscape architect, is Simon Baker. While the movie makes fun of their differences culturally, it doesn’t minimize the serious concerns Kenya has over how the rest of the world sees them. Despite the deck being stacked against their love, you’re rooting for Kenya to take the leap and try, you guessed it, something new.

It’s available on HBO Max

Music & Lyrics (2007)

This Drew (Barrymore) and Hugh (Grant) double-hander is low-stakes compared to the other rom-coms of this decade: A washed up ‘80s pop star trying to write a hit for an up-and-coming teen singer with help from the lady who waters his plants. But there’s something so endearing about this pairing that it’s hard to resist. (Also, the movie’s faux one-hit wonder “PoP, Goes My Heart” is a real banger.) Grant agrees. “It’s impossible to hate,” he said during a 2021 appearance on Drew Barrymore Show. “We’re so good in it, and so charming.” Where’s the lie?

Amazon Prime Video – Rent It

Forgetting Sarah Marshall (2008)

Yes, this is the movie in which Jason Segel drops trou, but what the film’s writer and star really bares is his soul. While so many male-led rom-coms of this decade didn’t want to be seen as rom-coms, the How I Met Your Mother As a struggling Hollywood composer with a broken heart, the alum really shows off his emotions. When he heads to Hawaii to do what the film’s title suggests, he finds himself falling for a local named Rachel (Mila Kunis), who sees him through his worst, only to fall in love with him at his best: a composer of a puppet musical inspired by Mary Shelley’s Dracula.

You can watch it at Amazon Prime Video

The Proposal (2009)

Sandra Bullock was a master at playing the next-door girl for years. Now she is the boss of hell. Sandra Bullock plays the boss in comedy, which features a gender swapping on the “fake dating” trope. Margaret, the domineering doting aunt (played by Bullock), wants Andrew (Ryan Reynolds), to marry her in order for her to obtain a U.S. visa. The two must trick their family (including his grandma), before they can fool government officials. Betty White, into thinking they’re the real deal. The moment you click play you can see that these two rivals are about to fall in love. However, Bullock & Reynolds make it seem like they’re celebrating their victory.

It’s available on Hulu


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