The Best Romantic Comedies Of The 2000s, Ranked By Fans
- 1Kate Hudson, Matthew McConaughey, Adam Goldberg
How to Lose a Guy in 10 Days delivers an amusing war-of-the-sexes battle stacked with irresistible chemistry between leads - Kate Hudson and Matthew McConaughey. Directed by Donald Petrie, it revolves around Andie Anderson (Hudson), a journalist tasked with writing an article about driving away men using various tactics. She chooses advertising executive Benjamin Barry (McConaughey), unknowing that he has wagered his own bet involving dating women. This light-hearted romantic comedy captured audiences with its wacky premise while showcasing poignant insights into relationships.
- #396 of 769 onThe Most Rewatchable Movies
- #611 of 704 onThe All-Time Greatest Comedy Films
- #9 of 136 onThe 100+ Best Movies For Date Night
- 2Sandra Bullock, Ryan Reynolds, Mary Steenburgen
The Proposal provides a delightful take on the classic fake relationship trope with two powerhouse actors, Sandra Bullock and Ryan Reynolds, leading the charge. The film follows a Canadian executive who convinces her overworked assistant to marry her in order to avoid deportation. Directed by Anne Fletcher, this sophisticated comedy deftly explores themes of power dynamics, vulnerability, and love in unexpected places. It received praise for sharp dialogue and contributed memorable moments to pop culture, like Bullock's dance scene with Betty White.
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- #6 of 136 onThe 100+ Best Movies For Date Night
- #6 of 473 onThe 400+ Best Chick Flicks Ever
- #260 of 633 onThe 600+ Funniest Movies Of All Time
- 3Reese Witherspoon, Luke Wilson, Selma Blair
Legally Blonde turned Reese Witherspoon into America’s sweetheart when she portrayed sorority queen Elle Woods seeking justice by storming Harvard Law School after being dumped by her boyfriend Warner Huntington III (Matthew Davis). Director Robert Luketic successfully created an empowering story of self-discovery that challenges stereotypes about beauty versus intellect. The film's legacy includes a successful musical adaptation on Broadway and a much-awaited upcoming third installment, proving that persistence pays off.
More Legally Blonde- #189 of 769 onThe Most Rewatchable Movies
- #11 of 113 onThe Best Movies Of 2001
- #113 of 704 onThe All-Time Greatest Comedy Films
- 4Julie Andrews, Anne Hathaway, Héctor Elizondo
The Princess Diaries catapulted Anne Hathaway into stardom as she starred alongside Julie Andrews in this charming Cinderella-esque tale directed by Garry Marshall. Based on Meg Cabot's best-selling novel series, the story follows a nerdy high school girl named Mia Thermopolis who discovers she is heir apparent to the Genovian throne. Showcasing themes of empowerment and acceptance amidst royal responsibilities and societal expectations, The Princess Diaries was nominated for numerous awards — earning recognition for supporting performances from Heather Matarazzo and Hector Elizondo.
More The Princess Diaries- #319 of 769 onThe Most Rewatchable Movies
- #67 of 375 onThe Best Movies Based On Books
- #2 of 155 onThe 150+ Best Classic Tween Movies
- 5Jennifer Garner, Mark Ruffalo, Judy Greer
In 13 Going on 30, Jennifer Garner masterfully plays Jenna Rink – an adolescent who wishes to grow up overnight but grapples with the ramifications of her life choices. Mark Ruffalo stars opposite as the supportive best friend Matt, lending his charm and down-to-earth demeanor to counterbalance Jenna's chaotic journey. Directed by Gary Winick, this touching fantasy-comedy reminds viewers about the importance of authentic connections while aging gracefully.
More 13 Going on 30- #424 of 769 onThe Most Rewatchable Movies
- #43 of 155 onThe 150+ Best Classic Tween Movies
- #25 of 99 onThe Best Movies Of 2004, Ranked
- 6Sandra Bullock, Michael Caine, Benjamin Bratt
Miss Congeniality showcases Sandra Bullock's knack for transforming unique characters into relatable personas: talent visible through her portrayal of Gracie Hart – a tomboyish FBI agent assigned to go undercover in a beauty pageant. Expertly led by director Donald Petrie, the movie offers rib-tickling humor and a sizzling dynamic between Bullock and love interest Benjamin Bratt. It also features a memorable performance from Michael Caine as Gracie's pageant coach, propelling the film to cult status in the rom-com repertoire.
More Miss Congeniality- #125 of 769 onThe Most Rewatchable Movies
- #104 of 704 onThe All-Time Greatest Comedy Films
- #7 of 473 onThe 400+ Best Chick Flicks Ever
- 7Katherine Heigl, James Marsden, Malin Akerman
27 Dresses marks Katheine Heigl’s transition into romantic lead territory as she successfully portrays Jane Nichols - a chronic bridesmaid who supports her sister's wedding plans despite harboring secret feelings for the groom-to-be (Edward Burns). Entrusted with writing columns documenting their romance is Kevin Doyle (James Marsden), whose alter ego is a pessimistic wedding reporter. Directed by Anne Fletcher, this heartwarming film narrates Jane's efforts to make others happy while learning how to commit when love is reciprocated.
More 27 Dresses- #18 of 473 onThe 400+ Best Chick Flicks Ever
- #36 of 82 onThe Greatest Female-Led Comedy Movies
- #128 of 185 onMovies With The Best Soundtracks
- 8Meryl Streep, Pierce Brosnan, Colin Firth
Mamma Mia! brought ABBA's timeless music back into cultural relevancy with an all-star cast including Meryl Streep, Amanda Seyfried, Pierce Brosnan, Colin Firth, and Stellan Skarsgård. Directed by Phyllida Lloyd, it tells the story of Sophie Sheridan (Seyfried) attempting to discover her father’s identity before her wedding day amidst sun-soaked Mediterranean shores. Adapted from its successful Broadway namesake musical counterpart - this feel-good film earned critical acclaim featuring infectious songs deconstructing themes regarding parenthood revelation creating perfect escapism for audiences.
More Mamma Mia!- #592 of 769 onThe Most Rewatchable Movies
- #9 of 204 onMusical Movies With The Best Songs
- #72 of 473 onThe 400+ Best Chick Flicks Ever
- 9Amanda Bynes, James Kirk, Channing Tatum
She’s the Man is a delightful modern retelling of William Shakespeare’s “Twelfth Night”, pulling in Amanda Bynes' comic genius as Viola Hastings – disguised as her twin brother at boarding school. Joining forces with Channing Tatum in his breakout role, they engage in entertaining onscreen banter under Andy Fickman's direction. This rom-com delves into themes revolving around gender roles and identity while providing comedic moments and captivating performances from emerging talents like Alex Breckenridge.
More She's the Man- #21 of 46 on50+ Quirky Romance Movies With Unique Love Stories
- #79 of 101 onThe Best Movies Of 2006
- #14 of 473 onThe 400+ Best Chick Flicks Ever
- 10Adam Sandler, Drew Barrymore, Rob Schneider
50 First Dates pairs Adam Sandler with Drew Barrymore in this unique romantic comedy set in Hawaii as they meet during unusual circumstances. Directed by Peter Segal, the film chronicles Sandler's character Henry Roth pursuing repetitive courtship due to Barrymore's Lucy Whitmore suffering from short-term memory loss. With a subtle exploration of disability and commitment at its core, 50 First Dates established itself as a heartfelt rom-com full of innovative storytelling devices punctuated by captivating scenic backdrops.
More 50 First Dates- Dig Deeper...50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman
- #113 of 769 onThe Most Rewatchable Movies
- #258 of 704 onThe All-Time Greatest Comedy Films
- 11Anne Hathaway, Julie Andrews, Héctor Elizondo
The Princess Diaries 2: Royal Engagement picks up where its predecessor concluded, continuing Mia’s (Anne Hathaway) journey into Genovian royalty under Queen Clarisse Renaldi's (Julie Andrews) careful watch. Directed by Garry Marshall once again, this coming-of-age comedy traces an arranged marriage executed for political reasons but is further complicated when Mona enters the picture alongside Nicholas Devereaux (Chris Pine). Supported by great ensemble cast performances and an unforgettable sleepover sing-along scene, it cemented The Princess Diaries' duo as beloved family movies with an epic romantic payoff.
- #61 of 99 onThe Best Movies Of 2004, Ranked
- #43 of 82 onThe 75+ Best Fairytale Movies
- #13 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- 12Hilary Duff, Jennifer Coolidge, Chad Michael Murray
A Cinderella Story reimagines the classic tale in a modern setting starring Hilary Duff and Chad Michael Murray. Mark Rosman’s direction revolves around high school romance blossoming amidst clever disguise centering themes of identity and destiny filled with witty dialogue perfect for young audiences craving updated fairy tales.
More A Cinderella Story- #70 of 136 onThe 100+ Best Movies For Date Night
- #62 of 82 onThe 75+ Best Fairytale Movies
- #19 of 473 onThe 400+ Best Chick Flicks Ever
- 13Reese Witherspoon, Josh Lucas, Patrick Dempsey
Sweet Home Alabama sees Reese Witherspoon starring as Melanie Smooter/Carmichael – a young woman on the cusp of marital bliss only to discover her past nuptials remain valid. Directed by Andy Tennant, viewers are reunited with one not-so-loveable ex-husband named Jake Perry (Josh Lucas), whose rekindled connection provides the perfect dose of quintessential Southern charm making audiences question which side they're rooting for while examining true love versus superficial attraction. This charming mash-up triumphs because Witherspoon convincingly balances vulnerability against determination proving there’s always hope regardless of how deep our roots go.
More Sweet Home Alabama- #264 of 769 onThe Most Rewatchable Movies
- #10 of 136 onThe 100+ Best Movies For Date Night
- #45 of 152 onThe Best Movies of 2002
- 14Sandra Bullock, Hugh Grant, Alicia Witt
Two Weeks Notice showcases Sandra Bullock and Hugh Grant's unbeatable chemistry as an ambitious attorney named Lucy Kelson and her charming yet needy boss George Wade – characters thrown into hilariously relatable scenarios involving professional collaboration turned tender affection. Marc Lawrence's directorial insight cleverly modernizes classic screwball comedy antics while providing an intriguing platform addressing issues concerning gentrification across urban landscapes, emphasizing love transcends personal convictions. It breaks down barriers and unites individuals despite stark societal contrasts.
More Two Weeks Notice- #97 of 152 onThe Best Movies of 2002
- #80 of 473 onThe 400+ Best Chick Flicks Ever
- #44 of 243 onThe Best Movies For Women
- 15Amy Adams, Patrick Dempsey, James Marsden
Enchanted is Disney's delightful blend of live-action and animation starring Amy Adams as Giselle – a naïve princess who falls victim to dastardly magic pushing her into reality's harsh world where she encounters NYC lawyer Robert Philip (Patrick Dempsey). Through David Lima's direction, viewers witness post-modern spin on fairy tales weaving together elements of romance, comedy, and musical genres. Fueled by stellar performances from the ensemble cast, including James Marsden and Susan Sarandon, Enchanted is a joyful experience that earned three Academy Award nominations for Best Original Song.
More Enchanted- #454 of 769 onThe Most Rewatchable Movies
- #101 of 452 onThe 400+ Best Animated Kids Movies
- #46 of 204 onMusical Movies With The Best Songs
- 16Hugh Grant, Laura Linney, Colin Firth
Love Actually is a star-studded romantic comedy weaving together multiple love stories amidst the holiday season. Directed by renowned writer Richard Curtis, this beloved film stars countless talented actors, including Hugh Grant, Emma Thompson, Colin Firth, Keira Knightley, and Alan Rickman. Its exploration of different facets of love leaves us both heartbroken and hopeful as the intertwining narratives unfold while managing to touch upon serious topics like infidelity, grief, and unrequited love - all contributing to making Love Actually an enduring holiday classic.
More Love Actually- Dig Deeper...14 Disturbing and Heinously Sexist Things You Never Noticed About 'Love, Actually'
- #462 of 769 onThe Most Rewatchable Movies
- #34 of 126 onThe Best Christmas Movies Of All Time
- 17Amanda Bynes, Colin Firth, Kelly Preston
What a Girl Wants takes us on a journey with Amanda Bynes playing Daphne Reynolds, an American teenager reconnecting with her estranged British father. Directed by Dennie Gordon, this film merges comedy and emotion while underlining the concept of self-identity during adolescent years within familial relationships.
More What a Girl Wants- #48 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- #52 of 473 onThe 400+ Best Chick Flicks Ever
- #39 of 82 onThe Greatest Female-Led Comedy Movies
- 18John Cusack, Kate Beckinsale, Molly Shannon
Serendipity is an enchanting John Cusack and Kate Beckinsale-led film that emphasizes the idea of "meant to be." Directed by Peter Chelsom, the movie follows the two leads as they toe the line between fate and free will after sharing a chance encounter in New York City. Stunning visuals from iconic locations summon millions toward its unique quality while threading a delicate depiction of love's grand design that challenges viewers' perception of destiny.
More Serendipity- #89 of 126 onThe Best Christmas Movies Of All Time
- #52 of 113 onThe Best Movies Of 2001
- #36 of 136 onThe 100+ Best Movies For Date Night
- 19Renée Zellweger, Colin Firth, Hugh Grant
Bridget Jones’s Diary explores Renee Zellweger’s transformation into Helen Fielding’s beloved titular character facing life choices while being caught up between two prospective suitors: her dashing boss (played by Hugh Grant) and standoffish childhood friend (portrayed by Colin Firth). Sharon Maguire brilliantly recreates London on-screen with humor-spirited dialogue while traversing themes such as body image stigma fulfillment challenges faced amid late-stage singledom;The movie received accolades throughout Hollywood, proving itself a consummate 2000s-era rom-com.
- #660 of 769 onThe Most Rewatchable Movies
- #37 of 113 onThe Best Movies Of 2001
- #48 of 136 onThe 100+ Best Movies For Date Night
- 20Ryan Reynolds, Isla Fisher, Abigail Breslin
Definitely, Maybe follows Ryan Reynolds' effortlessly charming portrayal of Will Hayes —a father explaining his complex past relationship history to his daughter— while connecting dots that lead them to her mother's identity. Overflowing with heartwarming anecdotes backed by Elizabeth Banks, Isla Fisher, and Rachel Weisz, who collectively portray Will's former loves, writer-director Adam Brooks skillfully crafts a layered cinematic experience that doubles as a nostalgic time capsule traversing early 90s politics through plots full of twists and turns.
More Definitely, Maybe- #85 of 473 onThe 400+ Best Chick Flicks Ever
- #15 of 57 onThe Best Single Dad Movies Ever Made
- #33 of 87 onThe 80+ Best Father-Daughter Movies
- 21Jennifer Lopez, Matthew McConaughey, Bridgette Wilson-Sampras
The Wedding Planner stars Jennifer Lopez as Mary Fiore – an up-and-coming wedding planner who accidentally falls for her biggest client's fiancé Steve Edison (Matthew McConaughey), leading to unexpected chemistry and chaos. Directed by Adam Shankman, his romantic comedy excels in balancing heartache with hope as characters struggle through their feelings against professional obligations.
More The Wedding Planner- #62 of 113 onThe Best Movies Of 2001
- #60 of 136 onThe 100+ Best Movies For Date Night
- #45 of 473 onThe 400+ Best Chick Flicks Ever
- 22Debra Messing, Dermot Mulroney, Amy Adams
The Wedding Date features Debra Messing in a captivating performance as Kat Ellis – a woman who hires a male escort (Dermot Mulroney) to be her date for her sister's wedding. Directed by Clare Kilner with charming chemistry between leads resulting from great dialogue delivery showcasing their prowess in mastering various comedic scenarios throughout believable performances, it manages simultaneously remind viewers despite the seemingly cynical outlook culture regarding online dating evolution over time… nonetheless, there remains risk involved vulnerability required truly embrace connection genuine partnership experience reflecting lighthearted humor romance-based cinema enjoyment audiences everywhere.
More The Wedding Date- #103 of 143 onThe Best Movies of 2005
- #110 of 473 onThe 400+ Best Chick Flicks Ever
- #8 of 25 onIf Your Partner Suggests Any Of These Movies, They Want An Engagement Ring
- 23Ben Affleck, Jennifer Aniston, Drew Barrymore
He's Just Not That Into You is an ensemble rom-com starring Jennifer Aniston, Ben Affleck, Scarlett Johansson, and more. Directed by Ken Kwapis, this charming and honest take on modern relationships captures the complications and interconnections within the dating world, making it a relatable experience for viewers.
- #104 of 473 onThe 400+ Best Chick Flicks Ever
- #13 of 60 onRomantic Movies Your Girlfriend Forces You To Watch
- #224 of 243 onThe Best Movies For Women
- 24Will Smith, Eva Mendes, Kevin James
Hitch showcases Will Smith as New York City's "Date Doctor," who seemingly has all answers until he meets gossip columnist Sara Melas (Eva Mendes). Under Andy Tennant’s direction, it provides a humorous insight into dating intricacies against the vibrant Manhattan backdrop.
More Hitch- #605 of 704 onThe All-Time Greatest Comedy Films
- #71 of 136 onThe 100+ Best Movies For Date Night
- #41 of 143 onThe Best Movies of 2005
- 25Isla Fisher, Hugh Dancy, Krysten Ritter
Confessions of a Shopaholic allows Isla Fisher to shine as Rebecca Bloomwood – a young woman drowning in debt yet seeking employment within the high-flying world of finance journalism under Luke Brandon’s tutelage (played by Hugh Dancy). P.J Hogan’s directing expertise creates a visually lush landscape peppered with hilariously chaotic moments, offering not only laughs but also an underlying commentary on consumerist cultural values.
- #314 of 375 onThe Best Movies Based On Books
- #76 of 473 onThe 400+ Best Chick Flicks Ever
- #157 of 185 onMovies With The Best Soundtracks
- 26Jennifer Lopez, Ralph Fiennes, Natasha Richardson
Maid in Manhattan showcases Jennifer Lopez as Marisa Ventura, a hotel maid mistaken for a socialite by a charming politician (Ralph Fiennes). Directed by Wayne Wang, the film perfectly blends themes of deception and love while highlighting the importance of staying true to oneself.
More Maid in Manhattan- #80 of 136 onThe 100+ Best Movies For Date Night
- #87 of 152 onThe Best Movies of 2002
- #64 of 473 onThe 400+ Best Chick Flicks Ever
- 27Owen Wilson, Vince Vaughn, Christopher Walken
Wedding Crashers features Owen Wilson and Vince Vaughn as two adventurous friends who crash weddings only to find real connections. Directed by David Dobkin, the film draws laughter with light-hearted humor threaded through romantic predicaments for its characters.
More Wedding Crashers- #335 of 769 onThe Most Rewatchable Movies
- #67 of 704 onThe All-Time Greatest Comedy Films
- #73 of 136 onThe 100+ Best Movies For Date Night
- 28Kate Hudson, Anne Hathaway, Kristen Johnston
Bride Wars tests the limits of friendship between Liv (Kate Hudson) and Emma (Anne Hathaway), whose weddings end up on the same day. Gary Winick directs this comedic take on bridal competition, unraveling deep-rooted emotions amidst outrageous fights and misunderstandings, earning an entertaining watch.
More Bride Wars- #78 of 89 onThe Most Rewatchable Comedy Movies
- #66 of 473 onThe 400+ Best Chick Flicks Ever
- #46 of 82 onThe Greatest Female-Led Comedy Movies
- 29Jason Segel, Kristen Bell, Mila Kunis
Forgetting Sarah Marshall follows composer Peter Bretter (Jason Segel) struggling to get over his TV actress ex-girlfriend on a picturesque Hawaiian vacation. Directed by Nicholas Stoller, it provides relatable humor steeped in heartache and self-discovery set amid breath-taking locations making it a memorable addition to the rom-com genre.
- #626 of 769 onThe Most Rewatchable Movies
- #371 of 704 onThe All-Time Greatest Comedy Films
- #59 of 136 onThe 100+ Best Movies For Date Night
- 30Patrick Dempsey, Michelle Monaghan, Kevin McKidd
Made of Honor stars Patrick Dempsey as Tom – a platonic friend who realizes his love for Hannah (Michelle Monaghan) when she asks him to be her "maid" of honor. Paul Weiland's rom-com showcases the importance of friendship in romantic relationships delivering an enjoyable journey navigating complicated emotional terrains.
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