The 25 Best Romantic Comedies of the Last 25 Years

2023 closed out with the shrug heard around the world, the solid-triple hit that was the romantic comedy Anyone But You. It was a fun little film that served much-missed romantic comedy tropes, showcased Glen Powell’s seemingly endless reserves of charm, and acknowledged, yet played to, Sydney Sweeney’s lack of physical comedy chops. Importantly, it made money. To paraphrase Mark Twain or Diane Lane or someone: “The reports of the death of the Rom Com have been greatly exaggerated.”

Now, anyone with their college roommate’s cousin’s Netflix password knows that romantic comedies have been alive and well on streaming services for the past decade. Even if you forget the Christmas Rom Com industrial complex (as this list will in just a moment), you can’t ignore the existence of the Kissing Booths and To All the Boys trilogies, among many other romps reaching various levels of romantic comedy euphoria. Netflix, YA novel adaptations and homophobic Christmas movie channels have been doing their best to keep the genre alive.

In 2024, some of the greatest rom coms ever, including Notting Hill, The Proposal, When Harry Met Sally, Romancing the Stone, (500) Days of Summer, and 13 Going on 30, to celebrate milestone anniversaries. With that much history behind us and a bit of a resurgence ahead of us, now’s the perfect time to count down the 25 Best Romantic Comedies of the last 25 years.

A few ground rules: I took this very literally, so only films from the summer of 1999 to through spring of 2024 were eligible (sorry to 10 Things I Hate About You, She’s All That, and Never Been Kissed).

Also, have you guys heard of the patriarchy? It’s alive and well in, in of all places, the internet! If you Google romantic comedies of any given year, dozens of films will come up. More than half of them will simply be films starring women. According to the World Wide Web, the only thing that makes a movie a romantic comedy is a prominent female lead who may – or in some cases may not – have a male love interest. Here is an almost comical, and infuriatingly long list of films that are disqualified for simply not being a romantic comedy: Miss Congeniality (a straight-up comedy), Moulin Rouge! (musicals are not inherently comedies/she has consumption!), The Sweetest Thing (a female buddy road movie), Holes (not the film I thought it was going to be), 40- Year- Old Virgin (admittedly on the borderline, but this is more a sex comedy), Monster-in-Law (I don’t know what this is, but it certainly isn’t a rom com), House Bunny, Legally Blonde, Easy A, (female fronted comedies).

A last note: I couldn’t include holiday films because they would’ve eaten up half the list. I am sorry!

So, without further ado, here are the Best Romantic Comedies of the Last 25 Years:

25. Crazy, Stupid, Love (2011)

The biggest knock against Crazy, Stupid, Love is how boldly it is trying to be a James L. Brooks elevated rom com. If you ignore that, the uncomfortable stalker behavior exhibited by the son of Steve Carrell and Julianne Moore and the teenage babysitter taking naked pictures for an adult man (also Steve Carrell), it’s a pretty affecting, well-acted, well-written multi-generational movie that has some surprises up its sleeve. But let’s be honest, the real draw here is Ryan Gosling as a lothario showing Steve Carell’s sad sack recent divorcee the ropes of dating (read: getting laid). Gosling is funny, slimy, tender, and hot in a way that I can’t guarantee is legal. His chemistry with Emma Stone, in an unfortunately underwritten role, is out of this world.

24. Sweet Home Alabama (2002)

Reese Witherspoon’s innate Reese-ness and Josh Lucas’s smoldering Paul Newman impression are the highlights here. Sweet Home Alabama is a pretty standard rom com about a down-home southern girl who must head down home to get a divorce from her long-forgotten childhood sweetheart so she can marry Patrick Dempsey, going full- McDreamy three years before Seattle Grace even opened its doors. I don’t return to this one this often, but when a legend is born, respect must be paid. Reese Witherspoon – you’ll always be famous!

23. 13 Going on 30 (2004)

Some films are too emblematic of the genre not to be included. 13 Going on 30 is a twist on the ‘I wish I was an adult and all my problems would certainly be solved and not at all get worse by the crushing pain of day-to-day existence’ films. In it, young Jenna dreams of being popular, pretty, and maybe a little terrible. It’s a Jennifer Garner charm bonanza, quite simply one of our most watchable actresses. This is also a film that turned a generation of boys gays every time thanks to the presence of Mark Ruffalo and, of the many Judy Greer BFF roles, Tom-Tom is the best because she seems to be pure evil.

22. Going the Distance (2010)

So early for such a big swing, I know. But this movie is such a genuine fun romp, I couldn’t ignore it. Then real-life couple Drew Barrymore and Justin Long are a long-distance couple facing some real (and some very funny) issues of dating across the country in a pre-FaceTime/Snapchat/whatever people use for digital sex nowadays era. A list about rom coms doesn’t seem complete without Drew Barrymore, who we’re always just one TikTok trend away from the youths finding out was one of the biggest movie stars on the planet before she became everyone’s favorite cool aunt. 

21. To All the Boys I’ve Loved Before (2018)

At this point in my life, most YA-focused films on streaming services are simply not for me. And that’s OK! My parents didn’t need Dawson’s Creek the same way I don’t need Outer Banks. However, this Netflix hit was for everyone, mostly thanks to stars Lana Condor and Noah Centineo and a sharp script by Sofia Alvarez. Centineo is a Jake Ryan-level heartthrob, and I can’t describe Lana Condor in any more positive way than saying she’s giving me peak Robyn Lively vibes from the 80s and 90s.

20. The Wedding Planner (2001)

This might not be the best movie on the list but the J. Lo Rom Com industrial complex must be acknowledged, respected, and appreciated. The innate hilarity of a wedding planner who can’t find love is such a pitch-perfect rom com set-up that the only way it could be elevated further is by having early-aughts Jennifer Lopez and Matthew McConaughey be its stars. An almost flawless encapsulation of what makes rom coms a genre worth celebrating. I won’t be elaborating on this further.

19. It’s Complicated (2009)

Choosing a favorite Nancy Meyers rom com is like picking a favorite Nancy Meyers kitchen: They’re gleaming, beautiful to look at, and very white (from the countertops to the cast). Despite a glaring lack of diversity, Nancy’s ability to create a funny, gorgeous world to wrap oneself up in like a trademark cashmere V-neck sweater simply can’t be ignored. This one sees Meryl Streep having an affair with her ex-husband Alec Baldwin while falling in love with sweet architect Stevearchitect, Steve Martin. It’s a bit slight but thanks to a strong cast and an incredibly game Streep, fully in her unexpected Most Bankable Actress in Hollywood era, it’s re-watchability index is through the roof.

18. Two Weeks Notice (2002)

I know I am the one who name-checked The Proposal in the introduction to this list, but I’ll take Sandra Bullock and Hugh Grant over Sandy and Ryan Reynolds any day. In fact, Sandra took a seven-year hiatus from rom coms because she felt she reached the height of the form with this story of a strait-laced lawyer (Bullock) working for a, tell me if you’ve heard this one before, rakish charming cad of a businessman (Grant). I defy you not to watch this one without a smile slapped across your face.

17. Set It Up (2018)

When we’re talking about undeniable rom com vibes, one of the last to absolutely nail it was this Zoey Deutch-Glen Powell Netflix vehicle about two of the most gorgeous office peons on earth being kept from dating by their demanding and equally hot bosses (Lucy Liu and Taye Diggs). Deutch proved herself to be a formidable rom com heroine, who I wish we were seeing more regularly in this (kind of role. And Glen Powell… I mean, what’s left to say about Glen Powell? He was born for this.

16. 27 Dresses (2008)

Before the internet decided that it was time to hate Katherine Heigl, we all loved her transition from Izzie Stevens on Grey’s Anatomy to the always-a-bridesmaid star of this rom-comrom com hit. Flanked by best friend Judy Greer (drink!) and Malin Akerman, as the sister whose wedding is her final straw, Heigl is incredibly winning. Being wooed by James Marsden doesn’t hurt either.

15. Bros (2022)

This was the spot I allotted for a polarizing pick, in this case choosing Bros instead of the more influential but significantly more annoying (500) Days of Summer. While this film didn’t set the box office on fire as, and perhaps too much was made of its groundbreaking nature, at its heart Bros is a deeply funny and moving film that hits all the beats of a rom com in a very well-realized gay world. Writer-star Billy Eichner’s script nails dating in the world of circuit parties and Grindr notifications. In supporting roles, Ts Madison and Bowen Yang steal the show, while Luke Macfarlane, fresh out of Hallmark film purgatory, is a rom com revelation as the love interest who must learn to prioritize intimacy over sex (and foursomes).

14. Nick and Norah’s Infinite Playlist (2008)

I refuse to call this film quirky, but it’s hard to find another word for a rom-com starring Michael Cera and Kat Dennings on a spontaneous night in New York City, filled with music and swoony moments. Dennings is so great here, it’s almost a shame this led directly into a decade-long stint on 2 Broke Girls because it would’ve been great to see her in more lead roles on the big screen. Cera doesCera, does a surprisingly effective job being a romantic lead, something that wasn’t necessarily on anyone’s career bingo card for him. But the winner of the film is Ari Graynor, as Nora’s hot mess express best friend. How she’s not the biggest star in the world, I’ll never understand.

13. Always Be My Maybe (2019)

If you only know her from her standup specials or as a warring woman on a rampage escalating from petty to oh my God horrific revenge, do yourself a favor and check out Ali Wong in Always Be My Maybe. She’s rom com gold in this movie about childhood romance rekindled. Randall Park is dashing and funny as the one who constantly got away. The extended cameo by Keanu Reeves is the best use of celebrity in the last decade.

12. Forgetting Sarah Marshall (2008)

Jason Segel’s naked performance and Kristen Bell as the ex who broke his heart (and TV star of the wonderfully titled Crime Scene: Scene of the Crime), elevate this whip-smart comedy to near-classic status. The best of the Apatow-produced comedies of the time, Forgetting Sarah Marshall is unfortunately tainted by the presence of scene-stealer Russell Brand, but nevertheless does an impressive job of balancing the sweet, the funny, the salty, and the absurd (that vampire puppet ending is an all-timer).

11. Something’s Gotta Give (2003)

Nancy, you’ve done it again! Nancy Meyers wrote and directed this romantic comedy ode to the Hamptons, white turtlenecks, and finding love over the age of 50. Diane Keaton stars as Erica, a divorced playwright forced to let her daughter’s much-older boyfriend, famous playboy Harry (Jack Nicholson), recover from a heart attack at her Hamptons home. Keaton earns every inch of her Oscar nomination making us believe that she’d fall more deeply in love with Jack Nicholson (sorry, Jack!) than Keanu Reeves as Julian, a thirtysomething doctor with the hots for Erica. This film also has the single greatest dissection of the ambiguity of the word “ya” vs. the clarity of the word “you.”

10. How to Lose a Guy in 10 Days (2003)

Hepburn and Tracy. Douglas and Turner. Roberts and Gere. Hudson and McConaughey. This hit about a columnist (Hudson) trying to write a how-to on making a man (McConaughey)  fall in love and dump her in just over a week should’ve set up two decades worth of pairings for this on-screen couple. Hudson is channeling her mother Goldie Hawn’s effortless charm while McConaughey is at his most lethal every time he smiles. Also Hudson’s yellow dress is one of the most iconic looks we’ve seen in recent memory.

9. Think Like a Man (2012)

I’d have never guessed in a million years that an antiquated, borderline offensive, how-to book written by none other than Steve Harvey would crack the 25 Best Romantic Comedies of the Last 25 Years, but here we are. The film has a chef’s kiss cast including Gabrielle Union, Michael Ealy, Taraji P. Henson, Meagan Good, Romany Malco, Kevin Hart, THE Regina Hall, and Turtle from Entourage, and more laughs than it deserves to wring out of the concept of women dating like men. It does the ensemble cast romantic comedy better than any of its contemporaries. Could you imagine if the 10th best movie on this list was Valentine’s Day, Mother’s Day, New Year’s Eve, or He’s Just Not That Into You? The sequel, featuring a full-on Bel Biv Devoe Poison video acted out by the female leads, is also not to be missed.

8. Sleeping with Other People (2015)

Writer-director Leslye Headland brings her acerbic, insightful Bachelorette lens to this under-the-radar gem. The film stars Alison Brie and Jason Sudeikis as two sex addicts who become besties, navigating love and friendship and then each other’s hearts and bodies. Alison Brie continues to prove herself to be one of the most interesting actors of her generation, and for those of you who like Sudeikis but have OD’ed on Ted Lasso positivity, you’ll love him in this.

7. Crazy Rich Asians (2018)

Everything about this movie is gorgeous: the cast, the locale, the opulent settings, the wedding! Constance Wu and Henry Golding lead this adaptation of the bestseller about a girl from the wrong side of the tracks and Golding, the 1% of 1%, who she falls in love with without knowing he’s one of the titular crazy rich Asians. Wu and Golding are a lovely match, but for my money, Michelle Yeoh as Golding’s overprotective mother is the star. Yeoh should have received her first Oscar nomination for the moment where she tells Wu’s Rachel, “you will never be good enough.”

6. My Big Fat Greek Wedding (2002)

My Big Fat Greek Wedding is the highest-grossing romantic comedy of all time for a reason: It’s really, really, really good. Nia Vardalos wrote the Oscar-nominated script based on her own overprotective, wacky Greek family that, for this Armenian-Bulgarian child of immigrants, felt very lived-in and authentic. Filled with laughs and deeply felt emotions about loneliness and responsibility towards family, My Big Fat Greek Wedding could have just been a fish-out-of-water comedy with a subplot about romance. But Vardalos makes Toula’s journey for independence and love with John Corbett so heartfelt that you end up leaving the theater thinking about that even more than how Andrea Martin was robbed of an Oscar nomination for playing lamb-loving, twin-eating Aunt Voula. (It was in the womb, relay!)

5. Down with Love (2003)

I’m a recent convert to the cult of Down With Love and my only question is: Why did I wait so long? If you get on this movie’s wavelength, it’s a perfect film. If you don’t get on its wavelength, watch it again and again and again until you do, because it’s worth it. Ewan McGregor and Renée Zellweger star in an homage to 1960s romantic comedies, that is as hilarious as it is biting. McGregor and Zellweger have possibly never been better as a feminist book author encouraging women to forgo romance in favor of sex and the slick magazine writer that wants to expose her as a fraud. They are buoyed by two tremendous performances from Sarah Paulson and David Hyde Pierce as their in-love-out-of-love best friends, and director Peyton Reed delivers a third-act twist that is downright Shyamalan-ian.

4. Pride and Prejudice (2005) / Fire Island (2022)

The sumptuous 2005 adaptation of Jane Austen’s romantic comedy novel of love, manners, and society gave a whole generation a new Mr. Darcy (pre-Tom Wambsgans Matthew Macfadyen) to swoon over and a new Elizabeth Bennett (Keira Knightley, breaking the shackles of *Pirates of the Caribbean*) to root for. The adventures of the Bennett sisters finding and losing and finding love may not be a laugh riot by 2005 standards, but I bet it had audiences rolling in the aisles in 1813 when it was first printed.

Fire Island is a modern reimagining of Pride and Prejudice set in the LGBTQ+ haven of the title, with gay men standing in for the Bennett sisters and their various love interests. While this gay New Yorker (Long Islander, even) finds the sights very familiar – almost missing the ferry, Low Tea at The Blue Whale, the Underwear Party at the iconic Ice Palace – it’s star-screenwriter Joel Kim Booster’s clever, genuinely funny, and moving script that places it so high on the list. The cast, including Booster, Bowen Yang, James Scully, Margaret Cho, and and scorchingly hot Conrad Ricamora as the Mr. Darcy analog are all solid, but it’s Matt Rogers, Tomas Matos, and that one gay guy at the party who continually doesn’t recognize Joel Kim Booster who steal every scene they’re in.

3. Long Shot (2019)

Long Shot is one of cinema’s biggest pre-pandemic moviegoing shames. This should’ve been an easy $100 million hit, sparking the very conversation about rom com resurgence we are having right now. Alas, audiences didn’t show up to see Charlize Theron as the Secretary of State unexpectedly fall in love with Seth Rogen’s reporter-turned-speechwriter. Our loss because this movie is wonderful and the only one I can think of to center its climax on a leaked video of its lead male jerking off. The magic of the movie is thanks in large part to Liz Hannah and Dan Sterling’s whipsmart script, frequent Rogen collaborator Jonathan Levine’s confident direction, and the chemistry between Theron and Rogen being so strong you never really wonder why she’s with him. Bonus points for any film that so prominently features June Diane Raphael in position of power.

2. Bridget Jones’s Diary (2001)

Is it surprising that there are three “versions” of Pride and Prejudice in this Top 10? Not really; It’s the most famous novelnovels in the world. Is it an absolute wake-up-with-your-hair-on-fire shock that there are two Renée Zellweger vehicles in that same Top 10? Well, yes. But it’s undeniable that Zellweger’s performance as the British single gal who smokes too much, drinks too much, shags too much, and eats too much (her words not mine!) is forever ensconced in the film character hall of fame. Hugh Grant playing against type, starting down the road towards his current villain from Paddington/Ashley Graham nemesis persona, is a brilliant master stroke. Equally clever and effective is casting Colin Firth, Mr. Darcy from the seminal BBC version of Pride and Prejudice, as this world’s version of, you guessed it, Mr. Darcy. A romp with heart from the beginning lip sync to All By Myself to the fight in the snow over Bridget’s love, this one is for the history books.

1. Notting Hill (1999)

It’s the reason for the season! It’s easy to forget that 1999 was the Summer of Julia. Fresh off her “comeback” with My Best Friend’s Wedding, a film that would top this list if we went back a mere two years, and a Christmas hit in Stepmom, Julia had not one but two massive films between May and August 1999: Notting Hill and Runaway Bride.

While Runaway Bride is notable for reuniting the Pretty Woman trio of Julia Roberts, Richard Gere, and director Garry Marshall (not to mention supporting player Hector Elizondo), it would stretch credulity even for me to place it on this list. A fun frolic through old times, sure, but an evolution of the form it is not. Have I watched it 100 times, yes, but my journalistic integrity won’t allow me to place it on the list. Call the Pulitzer board!

But Notting Hill is quite another story. It’s a beautiful little film that gets caught under the banner of rom com (derogatory) instead of rom com (complimentary). Julia Roberts plays Anna Scott, the most famous actress in the world, beset by paparazzi and scandal, who happens into Hugh Grant’s travel bookshop “with the blue door.” Roberts and Grant make a romantic duo for the ages. Grant has never been more delightfully foppish and stutteringly endearing. Roberts gives one of her best, most underrated performances, as an actress who can’t help being vain, winning, gorgeous, insecure and almost pathologically charming. She has a monologue at a dinner scene with Hugh Grant’s group of delightfully British friends about the perils of fame that I’d put up against anything in her career. 

But in the end, it comes down to her “just being a girl, standing in front of a boy, asking him to love her”, 25 years later, and still one of the most famous lines on this list. And the reason why rom coms should never go out of style.