Nothing will take you back to the turn of the century like early 2000s rom-coms – they dominated the box office and inspired many to find true love. During this time, rom-coms started introducing more relatable plots, opposed to the typical story often depicted in the 20th century.
Some of you might be wondering – what is a rom-com? It’s nothing more than a shortened form of ‘romantic comedy.’ A romantic comedy film combines everything a woman likes in a chick flick and everything a man likes in a comedy. It’s what we like to call the best of both worlds.
That’s why early 2000s rom-coms make for the perfect date night movie with your significant other. It doesn’t matter what the occasion is, what day of the week it is, what type of snacks you’re munching on, or how many other couples join – you can’t go wrong with a rom-com date.
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Early 2000s Rom Coms You Should Watch Tonight!
For those that were alive at the turn-of-the-century, watching early 2000s rom-coms will be a nostalgic experience, especially considering it was two decades ago. If you had a favorite actor or actress back then, chances are they were in a romantic comedy at some point in the 2000s.
We’re talking Renée Zellwegger, Reese Witherspoon, Drew Barrymore, Adam Sandler, Jessica Alba, Will Smith, Seth Rogen, Katherine Heigl, Ryan Reynolds, Mila Kunis, Jason Segel, Sandra Bullock, and more – they were all featured in popular early 2000s rom-coms.
With over 100 different films that would qualify as early 2000s rom-coms, we’re going to make your date night a little easier by narrowing your options down to our favorite 25. Don’t worry, I’m sure your all-time favorite is here somewhere – here’s to a wonderful night with beautiful people!
25. Two Can Play That Game (2001)
Two Can Play That Game was released in 2001. The romantic comedy was written and directed by Mark Brown, and stars Vivica A. Fox, Morris Chestnut, Anthony Anderson, Gabrielle Union, Mo’Nique, Tamala Jones, and more. It’s about a boyfriend and girlfriend who continue to play mind games with one another as their arrogant attitudes clash time and again.
24. Along Came Polly (2004)
Along Came Polly was released in 2004. The romantic comedy was written and directed by John Hamburg, and stars Ben Stiller, Jennifer Aniston, Debra Messing, Philip Seymour Hoffman, and Alec Baldwin. It’s about a man who finds his wife cheating on him and later ends up falling in love with an old classmate. His normally-organized life quickly turns into chaos.
23. Wedding Crashers (2005)
Wedding Crashers was released in 2005. The romantic comedy was written by Steve Faber and Bob Fisher, directed by David Dobkin, and stars Owen Wilson, Vince Vaughn, Rachel McAdams, Christopher Walken, Isla Fisher, Bradley Cooper, and Jane Seymour. It’s about two friends who frequently crash weddings to hook up with women, but end up finding love.
22. The Sweetest Thing (2002)
The Sweetest Thing was released in 2002. The romantic comedy was written by Nancy M. Pimental, directed by Roger Kumble, and stars Cameron Diaz, Thomas Jane, Christina Applegate, Lillian Adams, and Jason Bateman. It’s about a woman who spends her entire life trying to avoid men, but things change when she finally finds the one she’s destined to be with.
21. Fool’s Gold (2008)
Fool’s Gold was released in 2008. The romantic comedy was written by John Claflin, Daniel Zelman, and Andy Tennant – Tennant was also the director. It stars Matthew McConaughey, Kate Hudson, Donald Sutherland, Alexis Dziena, Ewen Bremner, Kevin Hart, and Ray Winstone. The film is about a married couple who sets out on an adventure to find treasure.
20. Good Luck Chuck (2007)
Good Luck Chuck was released in 2007. The romantic comedy was written by Josh Stolberg and Steve Glenn, directed by Mark Helfrich, and stars Dane Cook, Jessica Alba, Dan Fogler, Connor Price, Sasha Pieterse, and Troy Gentile. It’s about a man who’s destined to break a curse – if he sleeps with anyone, the next man they meet will be their true love.
19. My Big Fat Greek Wedding (2002)
My Big Fat Greek Wedding was released in 2002. The romantic comedy was directed by Joel Zwick and written by Nia Vardalos – who also starred in the film alongside John Corbett, Michael Constantine, and Christina Eleusiniotis. It’s about a young Greek woman who attempts to get her family to accept her non-Greek lover. She struggles at first, but it works out.
18. Something’s Gotta Give (2003)
Something’s Gotta Give was released in 2003. The romantic comedy was written and directed by Nancy Meyers, and stars Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet, Frances McDormand, Jon Favreau, and Paul Michael Glaser. It’s about an older man who used to live life as a swinger, but changes paths and falls in love with an accomplished woman.
17. The Holiday (2006)
The Holiday was released in 2006. The romantic comedy was written and directed by Nancy Meyers – the same person who wrote and directed Something’s Gotta Give. The film stars Kate Winslet, Cameron Diaz, Jude Law, Jack Black, Eli Wallach, and Edward Burns. It’s about two women who swap homes in different countries and end up falling in love with local men.
16. Amélie (2001)
Amélie was released in 2001 and was one of the first early 2000s rom-coms that came out. It was written and directed by Jean-Pierre Jeunet – and co-written by Guillaume Laurant. The film stars Audrey Tautou, Mathieu Kassovitz, Rufus, Lorella Cravotta, Serge Merlin, and Jamel Debbouze. It’s about a woman who decides to help others and ends up falling in love.
15. Love Actually (2003)
Love Actually was released in 2003. The romantic comedy was written and directed by Richard Curtis, and stars Hugh Grant, Martine McCutcheon, Liam Neeson, Laura Linney, Bill Nighy, Gregor Fisher, Colin Firth, Emma Thompson, and more. Set a month before Christmas, the film tells the stories of eight different couples dealing with different issues in their love life.
14. Juno (2007)
Juno was released in 2007. The romantic comedy was written by Diablo Cody, directed by Jason Reitman, and stars Elliot Page, Michael Cera, Jennifer Garner, Jason Bateman, Allison Janney, J.K. Simmons, Olivia Thirlby, and Rainn Wilson. It’s about a young woman who’s faced with an unplanned pregnancy and decides to do something unusual with the unborn child.
13. A Cinderella Story (2004)
A Cinderella Story was released in 2004. The romantic comedy was written by Leigh Dunlap, directed by Mark Rosman, and stars Hilary Duff, Chad Michael Murray, Jennifer Coolidge, Dan Byrd, Regina King, Julie Gonzalo, and Lin Shaye. It’s about a young woman who anonymously starts messaging a young man. He turns out to be the cutest boy in school.
12. Fever Pitch (2005)
Fever Pitch was released in 2005. The romantic comedy was written by Lowell Ganz, Babaloo Mandel, and Nick Hornby, and directed by Bobby Farrelly and Peter Farrelly. The film stars Drew Barrymore, Jimmy Fallon, Jason Spevack, and Jack Kehler. It’s about a die-hard Boston Red Sox fan who’s forced to choose between a baseball team and the girl of his dreams.
11. Bridget Jones’ Diary (2001)
Bridget Jones’ Diary was released in 2001. The romantic comedy was directed by Sharon Maguire and written by Helen Fielding, Andrew Davies, and Richard Curtis. The film stars Renée Zellweger, Hugh Grant, Colin Firth, Gemma Jones, and James Faulkner. It’s about a young woman searching for love, all while keeping her thoughts in a personal diary.
10. The Princess Diaries (2001)
The Princess Diaries was released in 2001. The romantic comedy was directed by Garry Marshall and written by Meg Cabot and Gina Wendkos. The film stars Julie Andrews, Anne Hathaway, Hector Elizondo, Mandy Moore, and Heather Matarazzo. It’s about a young woman who finds out she’s the heir apparent to the throne of Genovia, which she humorously prepares for.
9. Knocked Up (2007)
Knocked Up was released in 2007. The romantic comedy was written and directed by Judd Apatow, and stars Seth Rogen, Katherine Heigl, Paul Rudd, Leslie Mann, Jason Segel, Jay Baruchel, Jonah Hill, and Iris Apatow. It’s about a party animal who accidentally knocks up a one-night stand. She shows up at his doorstep pregnant and they attempt to work things out.
8. She’s The Man (2005)
She’s The Man was released in 2005. The romantic comedy was directed by Andy Fickman and written by Ewan Leslie, Karen McCullah, and Kirsten Smith. The film stars Amanda Bynes, Laura Ramsey, Channing Tatum, Vinnie Jones, and David Cross. It’s about a young woman who disguises herself as her brother at his boarding school, where she falls in love.
7. The Proposal (2009)
The Proposal was released in 2009. The romantic comedy was written by Peter Chiarelli, directed by Anne Fletcher, and stars Sandra Bullock, Ryan Reynolds, Mary Steenburgen, Craig T. Nelson, Betty White and Denis O’Hare. It’s about a female boss who forces her male assistant to marry her in an attempt to maintain her visa status and avoid being deported.
6. The 40-Year Old Virgin (2005)
The 40-Year Old Virgin was released in 2005. The romantic comedy was written and directed by Judd Apatow (the mastermind behind Knocked Up). It was also co-written by Steve Carell, who starred in the film alongside Catherine Keener, Paul Rudd, Romany Malco, Seth Rogen, Elizabeth Banks, Leslie Mann, and Jane Lynch. As you guessed, it’s about a 40-year old virgin.
5. How to Lose a Guy in 10 Days (2003)
How to Lose a Guy in 10 Days was released in 2003. The romantic comedy was directed by Donald Petrie and written by Michele Alexander, Jeannie Long, Kristen Buckley, and others. The film stars Kate Hudson, Matthew McConaughey, Adam Goldberg, and Kathryn Hahn. It’s about a ladies man who bets that he can get a woman to fall in love with him within 10 days.
4. 13 Going On 30 (2004)
13 Going On 30 was released in 2004. The romantic comedy was directed by Gary Winick and written by Josh Goldsmith and Cathy Yuspa. The film stars Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis, Kathy Baker, and Phil Reeves. It’s about a 13-year old girl who makes a birthday wish, only to wake up the following day as a 30-year-old version of herself.
3. Hitch (2005)
Hitch was released in 2005. The romantic comedy was written by Kevin Bisch, directed by Andy Tennant (who also directed Fool’s Gold), and stars Will Smith, Eva Mendes, Kevin James, Amber Valletta, Julie Ann Emery, and Adam Arkin. It’s about an over-confident man falling in love with a columnist, all while helping his shy ‘friend’ win over a beautiful heiress.
2. 50 First Dates (2004)
50 First Dates was released in 2004. The romantic comedy was written by George Wing, directed by Peter Segal, and stars Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Lusia Strus, and Dan Aykroyd. It’s about a man who falls in love with a woman who has short-term memory loss. He spends his life trying to get her to remember him.
1. Forgetting Sarah Marshall (2008)
Forgetting Sarah Marshall was released in 2008. The romantic comedy was directed by Nicholas Stoller and written by Jason Segel – who starred in the film alongside Kristen Bell, Paul Rudd, Mila Kunis, Russell Brand, Bill Hader, Jonah Hill, and Jack McBrayer. It’s about a man trying to get over his ex by going on a vacation, just to bump into his ex – don’t worry, he also finds love.
Which Early 2000s Rom Coms Will You Watch?
I’m going to be honest, you might need to plan a couple more movie dates with your lover because there are simply too many early 2000s rom-coms worth watching – even if you’ve already seen them. In fact, I think some of them are even better the second time around!
Of course, there are also a lot of newer romantic comedies that have been released since 2020 – including Emma, Palm Springs, Happiest Season, The Half of It, Good On Paper, Crazy About Her, Coming 2 America, Book of Love, Marry Me, Moonshot, The Lost City, and much more.
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Whether you’re interested in watching a newer romantic comedy or want to indulge in one of the many early 2000s rom-coms we discussed above, there’s no better way to set the mood. It’s romantic enough to keep the women engaged, but funny enough to keep the men laughing.
If you’re looking for even more laughs, we’ve ranked all of Amy Schumer‘s best movies and TV shows. Revisit an old favorite or give something you haven’t seen yet a try! Schumer always swings big and almost never misses.
We Ranked Amy Schumer Movies and TV Shows from Least to Most Likely to Make You Laugh.
Snatched (2017)
What Is It About: Dumped by her boyfriend on the eve of their exotic vacation, impetuous dreamer Emily Middleton (Schumer) persuades her very careful mother, Linda (Goldie Hawn), to join her on an exotic getaway to South America. Polar opposites, Emily and Linda must soon work through their differences to escape from a wildly outrageous and dangerous jungle adventure.
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 36% out of 100%. So, not too fresh.
“They will be pleasantly mortified by the outrageous distances the movie travels to tickle its viewers, but in the end, the audience will be left asking: is this all there is?” one critic wrote of the film.
I Feel Pretty (2018)
What Is It About: An ordinary woman who has difficulty with feelings of insecurity and inadequacy on a daily basis wakes from a nasty fall believing she is suddenly the most beautiful and capable woman on the planet. With this newfound confidence, she is empowered to live her life fearlessly and without regret, but what will happen when she realizes her appearance never changed?
How It Was Received: Despite doing well at the box office, the film was not particularly loved by audiences or critics. According to Rotten Tomatoes, the film has an aggregate rating of 35% out of 100%.
“Like a few too many films churned out of the predominantly male studio system and marketed to a female audience, you get a sense that, deep down, it doesn’t have a particularly high opinion of women,” one critic wrote of the film and its outdated premise.
Amy Schumer: Mostly Sex Stuff (2012)
What Is It About: Nothing is off-limits for Schumer in her first original one-hour stand-up special. Schumer airs every hilarious, bizarre detail of her dating and sex life, from encounters with unexpected body parts to pain-filled personal grooming appointments.
How It Was Received: While Rotten Tomatoes does not have ratings for this comedy special, it was warmly received as a refreshing look at how women are expected to act and perform while trying to find love. A critic writing for The Guardian called it “comedy gold.”
“A light and very funny but nuanced and essentially feminist depiction of a world in which women know they can control men easily if they wear little and think less … but then stop to wonder sometimes, as they do so, who is really in control here. they wrote,” the critic wrote in their review.
Life & Beth
What Is It About: Beth’s life would look pretty great on paper. She makes a good living as a wine distributor. She’s in a long-term relationship with a successful guy and lives in Manhattan. When a sudden incident forces Beth to engage with her past her life changes forever. Through flashbacks to her teen self, Beth starts to learn how she became who she is and who she wants to become. We’ll go on her journey towards building a bigger, bolder, and more authentic life. Learning to express herself and living in an intentional way. A trip down memory lane is a strong source of trauma, comedy, and moving forward in this series.
How It Was Received: According to Rotten Tomatoes, the show has an aggregate rating of 92% out of 100%. That’s certified fresh!
“It’s frustrating that it takes until this sixth episode for some of the show’s puzzle pieces to find each other, but when they do, they make up a picture that’s more subtly moving than initially meets the eye,” a critic wrote favorably of the series for Variety.
Dying Laughing (2016)
What Is It About: Jerry Seinfeld, Kevin Hart, Amy Schumer, Chris Rock, Sarah Silverman, Jerry Lewis, Jamie Foxx, Garry Shandling, and others discuss the craft, creative process, and psychology of performing stand-up comedy before a live audience. It’s one of the first documentaries to feature Schumer but it’s not her last!
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 82% out of 100%.
“Dying Laughing masterfully weaves in a humanity to the art of stand-up no film has ever approached in terms of clarity,” one critic warmly wrote of the doc.
Amy Schumer: The Leather Special (2017)
What Is It About: Three minutes into her set, Schumer claims that all good comedians have a “leather special,” where they wear all leather and regret it later in their careers… this is hers. She muses on love, life, dating, and womanhood in her first Netflix comedy special.
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 50% out of 100%. So, a pretty polarizing comedy special.
One critic described the comedy special as “Packed with her signature blend of self-deprecation and graphic sex stories.”
Amy Schumer Learns to Cook (2020)
What Is It About: Amy and Chris Fischer (Schumer’s husband) are quarantined at home in Martha’s Vineyard with their nanny, who looks after baby Gene and runs the camera during naptimes. Chef Chris will prepare meals from their pantry with an assist from Amy. It’s a very DIY project from the couple that highlights the strange nature of living through a pandemic.
How It Was Received: Rotten Tomatoes does not have a rating for the cooking show but many viewers found the show, filmed in quarantine, to be refreshing and fun.
One critic for Variety wrote that the show was “Vital quarantine viewing.” They went on to call the show “a surprising, load-lightening watch.”
“She’s not telling as many jokes as one might expect, but, trapped somewhere in the woods and forced to cook her way out of boredom and towards connection with her husband as well as an audience stuck in their own quarantines, Amy Schumer is perhaps the most good-humored star of this challenging moment,” they also wrote of the show’s star.
Amy Schumer: Live at the Apollo (2015)
What Is It About: Directed by Chris Rock, Amy Schumer: Live at the Apollo is one of Schumer’s taped comedy specials. This one finds her entertaining audiences at the Apollo with her direct style of humor. The jokes keep coming in this spectacular comedy special that finds Schumer firing on all cylinders.
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 90% out of 100%. Pretty fresh!
“Schumer has matured, evolved into material that’s as thought-provoking as it is gut-busting, progressing from misdirectional pausing one-liners into long-form confessions and ruminations,” one critic wrote fondly of the comedy special.
Expecting Amy (2020)
What Is It About: Expecting Amy is a documentary series that documents the behind-the-scenes of Schumer’s extraordinarily difficult pregnancy while touring to prepare for a stand-up special. It’s the most intimate look that audiences have ever gotten from the comedian. It shows the humanity behind the jokes and how hard it can be to be a comedian while also carrying a child.
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 86% out of 100%.
“The series is more than a portrait of a fiendishly complicated pregnancy. (Schumer suffered from hyperemesis gravidarum, a condition marked by severe, prolonged nausea that lasts well beyond the first trimester and in her case led to several hospitalizations for dehydration),” one critic wrote of Expecting Amy. “It documents how, while enduring sickness beyond anything she’d been prepared for, Schumer continued to work, embarking on a 60-show tour of 42 cities and putting together a Netflix special called Growing.”
“Expecting Amy doesn’t just demystify pregnancy,” they continued. “It promises that pregnant people can do more than merely get through the day—that they can even continue to create and be enriched (as well as depleted) by what they’re going through.”
Amy Schumer: Growing (2019)
What Is It About: In this comedy special, Schumer gives a refreshingly honest and hilarious take on marriage, pregnancy, and personal growth. Filmed in front of a packed house in Chicago, the comedian talks about the joys of womanhood, settling into marital bliss, and yes also you guessed it… sex!
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 79% out of 100%. But, many critics were thrilled with her normalization of pregnancy and the difficulties that it can entail.
“Growing is a restatement of what Schumer does best: there are no new directions, but it proves that even on the precipice of motherhood, she is still the daddy of carnal standup,” one critic approvingly wrote. “Then, there is the material about Schumer’s pregnancy and the extreme vomiting that has accompanied it. She gleefully trashes pregnancy pieties, from the bump-cupping pose expectant mums strike in photos to those tedious (but flexible?) strictures around alcohol.”
The Humans (2021)
What Is It About: Set inside a pre-war duplex in downtown Manhattan, The Humans follows the course of an evening in which the Blake family gathers to celebrate Thanksgiving. As darkness falls outside the crumbling building, mysterious things start to go bump in the night and family tensions reach a boiling point. Based on the Tony award-winning play, this film is a triumph that showcases Schumer’s acting chops. Creepy, darkly funny, and powerful this drama is one of Schumer’s most humanist projects.
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 92% out of 100%. That’s as fresh as fresh gets.
“What starts as a family drama fades into a psychological thriller with the setting of the sun,” one critic wrote of the film. “Frivolous conversation turns to the family’s darkest secrets being revealed. The entire cast is exceptional.”
“The Humans features no ghosts, monsters, or poltergeists,” another critic noted. “It’s not set inside a haunted house, an abandoned building, or a tract of shadowy woods. And yet, it might be the scariest movie of the year.”
Trainwreck (2015)
What Is It About: Ever since her father drilled into her head that monogamy isn’t realistic, magazine writer Amy (Schumer) has made promiscuity her modus operandi. As much as she enjoys an uninhibited life free of commitment, Amy finds herself in a rut. While writing a profile about charming and successful sports doctor Aaron Conners (Bill Hader), she finds herself actually falling in love for the first time. What’s more, Aaron seems to like her too. Amy starts to wonder if it’s time to clean up her act. Hilarity ensues.
How It Was Received: According to Rotten Tomatoes, the film has an aggregate rating of 84% out of 100%. Not too shabby!
“Trainwreck is a complete blast,” one critic wrote of the film. “Even as it sends up rom-com clichés, it manages to be both seriously funny and genuinely romantic.”
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Inside Amy Schumer (2012)
What Is It About: Amy Schumer switches from sketches to doing stand-up to interviewing people on the street and people of interest, usually following a certain theme. Nothing is off-limits in this amazing sketch comedy series that finds Schumer playing a variety of characters and joking about all sorts of things.
How It Was Received: For starters, the show won a Peabody award in 2015. In addition to that achievement, the show won countless awards including a few Emmys. According to Rotten Tomatoes, the film has an aggregate rating of 86% out of 100%.
“Inside Amy Schumer is fearlessly feminist, defiantly woman-oriented, hysterically funny and so very, very dirty that parents will most definitely want to watch first before letting teens tune in,” a critic wrote of the show’s first season.
Amy Schumer has completed an impressive number of projects over the last couple of decades from her hilarious television shows to high-grossing films at the box office. There’s no shortage of laughs to be had watching anything she does so we hope you’ll try some of the movies and series on this list that you might have missed. You won’t regret it!
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