Top 10 Underrated Romantic Comedies of the 2000s
#10: “Music and Lyrics” (2007)
Hugh Grant and Drew Barrymore team up in this likable comedy about collaboration and finding your voice. Grant plays Alex, an eighties pop has-been who’s resigned himself to living in the past. Barrymore’s Sophie is a former aspiring writer who’s lost her confidence thanks to a toxic ex. While working together on a pop song for teen sensation Cora, romance and inspiration blossom. “Music and Lyrics” is not considered one of Hugh Grant’s best rom-coms but he brings his usual charm and humor, as does Barrymore. Despite the age gap, we root for Alex and Sophie and it's fun to watch them get wrapped up in the creative process. The songs are catchy and the side characters all do their bit to make us laugh.
#9: “Imagine Me & You” (2005)
LGBTQ+ movies can be pretty intense, so it’s nice when one comes along that offers gay people representation without attempting to be Oscar bait. “Imagine Me & You” is a sweet little rom-com about two women falling in love. The only problem is, one of them is already married. The central love triangle is well-handled and the characters manage to be likable despite their tangled personal lives. Lena Headey, Piper Perabo, and Matthew Goode make engaging leads and they tackle the rom-com cliches with charm. It might not have been a critical hit, but sometimes all you want is a fluffy romance movie and lesbians haven’t had their share yet.
#8: “Just My Luck” (2006)
Chris Pine is now better known for his sci-fi blockbusters, but he kicked off his career as a rom-com leading man - and he definitely understood the assignment. In “Just My Luck” Pine stars opposite Lindsay Lohan, who was breaking out of her high school roles. He plays Jake, a walking jinx who can’t catch a break, while she plays Ashley, who leads a charmed existence thanks to a lifelong lucky streak. When they kiss at a masquerade bash the luck gets switched and chaos and new experiences ensue. It’s one of Lohan’s lesser-known outings, but it definitely deserves revisiting. It’s a fun premise and there’s a tonne of chemistry between the leads. There are some great songs too from British boy band Mcfly.
#7: “Definitely, Maybe” (2008)
Ryan Reynolds shows off his leading man credentials in this “How I Met Your Mother”-style mystery that will keep you guessing until the very end. Abigail Breslin plays Reynolds’ young daughter, while Rachel Weisz, Elizabeth Banks, and Isla Fisher make up the trio of past loves. The script feels surprisingly fresh and any flaws are papered over by the charismatic cast. Breslin is a particular stand-out: she’s cute and funny without being cloying and provides us with a few genuinely moving moments. As rom-coms go, we think it deserves more love.
#6: “Bride and Prejudice” (2004)
Gurinder Chadha is the unacknowledged queen of the British noughties rom-com. The director brought us “Bend it like Beckham,” “Angus, Thongs and Perfect Snogging” and the brilliant “Bride and Prejudice” all within the space of a few years. But the latter movie is our favorite. A Bollywood twist on Jane Austen’s most famous novel, it still somehow flies under the radar. Aishwarya Rai stars as the Indian heroine, Lalita, while Martin Henderson gets under her skin as US hotel magnate, Will Darcy. This all-singing, all-dancing take on the classic tale is a real treat for Bollywood fans, Austen aficionados, and anyone who enjoys a good love story.
#5: “The Holiday” (2006)
“The Holiday” is an established Christmas classic, but we think it deserves appreciation as a romantic comedy in its own right. When two very different women switch homes for the holiday season, they discover that a quiet winter getaway is not on the cards. Instead, there are love and life lessons in store. The movie has a starry cast of warm, relatable characters, including Cameron Diaz, Kate Winslet, Jack Black, and Jude Law. Everyone’s in good form, but the real scene stealer is Eli Wallach as Arthur, an elderly screenwriter whom Winslet befriends. If you’re looking for a film to curl up on the couch with this winter, this cozy rom-com is the perfect choice.
#4: “John Tucker Must Die” (2006)
“Mean Girls” may be the definitive teen rom-com of the aughts, but its close cousin “John Tucker Must Die” deserves more recognition. Jesse Metcalfe is John Tucker, the most popular guy in school, who dates girls from different cliques so that they never find out about each other. Three of his past conquests join forces with new girl Kate to teach him a lesson, but the basketball star proves hard to bring down. It’s an interesting premise and the cast has a lot of fun with it, but it’s also surprisingly kind for a high school movie. Brittany Snow is a charming heroine and Penn Badgley makes an impression in an early role, playing the overlooked “other Tucker.”
#3: “Just Friends” (2005)
If bodysuits in movies make you cringe, don’t worry, you’re not the only one. But bear with us, because “Just Friends” isn’t just a one-joke comedy about a guy who lost weight to get the girl. It may not be super sophisticated but it’s not mean-spirited either thanks to the sympathetic characters. There are some nice undertones about friendship and inner beauty and a lot of warmth and heart. But mostly, it’s very funny. Anna Faris pushes her comedic muscles to the limit and shows off her singing voice too. Reynolds is the perfect choice for the lead role and Amy Smart and Chris Klein lend strong support.
#2: “Serendipity” (2001)
Like “The Holiday,” “Serendipity” is an easy-watching winter romance that deserves its place among such classics as “You’ve Got Mail” and “While You Were Sleeping.” John Cusack and Kate Beckinsale are the central couple - two strangers who have an instant connection while out Christmas shopping. However, they decide to go their separate ways until fate sends them a sign. For the movie to work, the viewer has to really believe that they’re meant to be - and luckily we do. The pair have great chemistry and an enjoyable rom-com rapport, which makes you hope that serendipity will indeed bring them back together again.
Before we unveil our top pick, here are a few honorable mentions.
“Just Like Heaven” (2005)
Mark Ruffalo & Reese Witherspoon Bring Star Quality to This Ghostly Love Story
“Kate & Leopold” (2001)
Hugh Jackman as a Time-Traveling English Duke? Count Us In!
“Lars and the Real Girl” (2007)
A Surprisingly Sincere Story About a Blowup Doll & Social Anxiety
“Chasing Liberty” (2004)
How Did We Sleep on Matthew Goode for So Long?
“Confessions of a Shopaholic” (2009)
The Story Feels Different & the Stars Keep the Laughs Coming
#1: “It’s Complicated” (2009)
This Nancy Meyers movie from 2009 proves that romantic comedies don’t all have to be about the young people - young at heart is good enough. Meryl Streep, Alec Baldwin, and Steve Martin make up the central love triangle in a story of divorce, adultery, old habits, and new beginnings. It’s not really so complicated though, just loads of fun. It’s easy to write off a middle-aged rom-com but as “Mamma Mia!” proved, if you get them right, they can still have mass appeal. “It’s Complicated” is thoughtful, fresh but most importantly, funny. The cast gives it everything, and when they’re having such a good time, it’s hard not to be swept along.