Romantic comedies have been around for decades, but they enjoyed a boom in the 2000s which can still bring on waves of nostalgia. Genre classics like 50 First Dates and How to Lose a Guy in 10 Days follow a tried and tested formula, and they have become great comfort movies which can be viewed over and over again. 2000s romantic comedies had a particular feeling to them that hasn’t been replicated since. Possibly thanks to the revolutionary success of Sex and the City, Hollywood became obsessed with witty rom-coms that weren’t afraid to be a little silly if that meant they were entertaining.
Romantic comedies are extremely relatable, because most people have experienced some sort of troubled with their love life, and these movies help make light of the situation. It’s enjoyable to watch a fun character struggling with love, and the happy endings resemble a kind of aspirational fantasy. Rom-coms of the 2000s often used outlandish premises to create stakes, and the heightened absurdity of the situations allowed for great comedy. Rom-coms have enjoyed a revival lately, but even great contemporary rom-coms don’t have the same feel of the early 2000s classics, and nostalgic fans will keep returning to their old favorites.
10 Kissing Jessica Stein (2001)
Romantic Leads: Jennifer Westfeldt & Heather Juergensen
A queer romantic comedy is a rare thing, but Kissing Jessica Stein is noteworthy for much more than just representation. Jennifer Westfeldt and Heather Juergensen wrote and co-produced the movie, as well as starring in it, and they share some fantastic dialogue scenes together, managing to weave jokes into dense ruminations on sexuality and self-discovery. Kissing Jessica Stein is astoundingly mature for a romantic comedy, eschewing the traditional saccharine finales of the genre for a more nuanced, bittersweet conclusion. Jessica and Helen don’t end up together, but they both grow and change after their shared experience. It’s very true to life, a minor disappointment tinged with optimism.
9 Bride & Prejudice (2004)
Romantic Leads: Aishwarya Rai & Martin Henderson
Bride and Prejudice is a Bollywood musical reimagining of Jane Austen’s seminal novel Pride and Prejudice. It’s a decidedly unfaithful adaptation, not just because of the setting, but also in the way it ignores Austen’s subtle sketches of profound loneliness in favor of a feel-good rainbow of sisterhood. Bride and Prejudice is not as serious as its source material. Its aim is to get people dancing, and to make people smile, and it succeeds on both fronts. Fans of the book may not even recognise the story, but Jane Austen never wrote a song as catchy as “No Life Without Wife,” so changes were necessary.
8 Bridget Jones’s Diary (2001)
Romantic Leads: Renée Zellweger & Colin Firth
Another adaptation of Pride and Prejudice, albeit a very loose one. Renée Zellweger her cult status as an honorary Brit with her performance as the appealingly flawed and gloriously vulgar Bridget Jones, caught in a love triangle between two men with their own considerable baggage. Bridget Jones’s Diary produced memorable quotes galore, and an even more memorable street fight between Colin Firth and Hugh Grant. It’s a rare romantic comedy that avoids sentimentality, reaching instead for a messy, downtrodden view of life. Despite this, Bridget Jones’s Diary is admirably, defiantly silly in a way that most modern comedies shy away from.
7 Hitch (2005)
Romantic Leads: Will Smith & Eva Mendes
Hitch posits that there is such a cutthroat attitude to dating in New York City that helpless men need to hire a suave love doctor just to stand a chance of talking to women without being immediately cast aside. Somehow, Will Smith and Kevin James make for such a fun on-screen duo that the absurd premise becomes forgivable. The student eventually becomes the master, as the anxious, dad-dancing Albert Brennaman teaches Hitch the value of being open and vulnerable. It’s a predictable outcome drawn in the broadest of strokes, but it’s endearingly optimistic, and Hitch banks enough good will to pull it off.
6 Legally Blonde (2001)
Romantic Leads: Reese Witherspoon & Luke Wilson
Like its main character Elle Woods, Legally Blonde struts with supreme confidence. After a shocking break-up, Elle enrolls in Harvard to impress her arrogant ex-boyfriend, but Legally Blonde quickly pivots from petty revenge to a tale about female empowerment. Reese Witherspoon shines as Elle, a perfect fish-out-of-water with the fantastic quality of knowing who she is, and an eye-catching outfit for every occassion. Packed with unforgettable Elle Woods quotes and a pitch-perfect Jennifer Coolidge, Legally Blonde shows that rom-coms don’t need to feature women being validated by the love of a man. Emmett is an appealing love interest because he respects Elle deeply. He’s a companion, not a savior.
5 50 First Dates (2004)
Romantic Leads: Adam Sandler & Drew Barrymore
After The Wedding Singer, Drew Barrymore and Adam Sandler teamed up once more for 50 First Dates. The movie works on the premise that Drew Barrymore’s character Lucy has short-term memory loss, and Adam Sandler’s Henry must win her heart again every single day. If the script probed a little deeper, some ethical questions would probably come up, or it could evolve into a strange horror movie from Lucy’s perspective. Fortunately, 50 First Dates is not concerned with philosophy to this degree, and Sandler and Barrymore’s playful exchanges are joyous to watch. 50 First Dates also benefits from a vomiting walrus, which can’t be said for most romantic comedies.
4 Last Holiday (2006)
Romantic Leads: Queen Latifah & LL Cool J
A lot of rom-com protagonists find happiness when they find true love, but Last Holiday offers an uplifting alternative message, that self-love is even more important. Queen Latifah plays Georgia, a shy salesperson who goes on a luxurious European holiday when she faces a terminal diagnosis. Her love interest, played by a charming LL Cool J, doesn’t share too much screen time with her, as Last Holiday prefers to spend time with Georgia discovering the joys of being alone. Last Holiday is based on a British movie from the 1950s, but it tweaks the ending to provide a happy Hollywood conclusion.
3 The 40-Year-Old Virgin (2005)
Romantic Leads: Steve Carell & Catherine Keener
Judd Apatow and Steve Carell’s script delights in subverting many of the essential tropes of rom-coms. In a genre so hyper-focused on watching young people discover what love is, The 40-Year-Old Virgin instead follows a middle-aged person discovering what sex is. Carell’s character Andy is backed up by a well-meaning but hopeless group of friends, each with their own misinformed opinions about what women want. The dialogue is typically excellent for Judd Apatow, but The 40-Year-Old Virgin’s chest waxing scene and ostentatious closing musical number are just two examples of the movie’s diverse comedic tastes. Apatow and Carell will do anything for a laugh, and it works wonderfully.
2 Love Actually (2003)
Romantic Leads: Too many to mention.
Richard Curtis’ intricate romance follows a series of barely interconnected couples in the weeks leading up to Christmas. Love Actually‘s incredible cast manage to keep each plate spinning, while providing some stories with a real depth of emotion. The asynchronous tonal shifts should not work this well, but Love Actually manages to juxtapose a zany side story about two pornography performers with a gut-wrenching tale of midlife divorce, propped up by the fantastic Emma Thompson. Love Actually is really nine or ten different rom-coms squeezed into one. Not all of them work flawlessly, but they contribute to a delightful final product.
A Selection of Some of Love Actually’s Couples | |
|---|---|
Emma Thompson | Alan Rickman |
Keira Knightley | Andrew Lincoln |
Martin Freeman | Joanna Page |
Colin Firth | Lucia Moniz |
Hugh Grant | Martine McCutcheon |
1 How To Lose A Guy In 10 Days (2003)
Romantic Leads: Kate Hudson & Matthew McConaughey
In many ways, How to Lose a Guy in 10 Days is the quintessential noughties rom-com. It ticks every necessary box: a romance that shouldn’t work, a leading couple with electric chemistry, and an exploration of the nature of love itself. Andie and Ben both have ulterior motives for pursuing their relationship, and the dramatic irony proves to be a near-inexhaustible source of comedy. How to Lose a Guy in 10 Days may perpetuate some harmful gender stereotypes by today’s more stringent standards, with Andie playing up the part of a clingy girlfriend, but the subversive plot deserves the benefit of the doubt.
