Ranking the Top 25 Rom-Coms of All-Time
25. LOVE, ACTUALLY
To officially kick off the best romantic comedies of all time, we have a classic. I mean the movie poster literally says it's "the ultimate romantic comedy." I don't think it's that great but Love Actually is the epitome of what romantic comedies bring to the table when done right. Specifically, the cards on the doorstep scene is one of the most iconic rom-com scenes around and is still parodied to this day thanks to its cute brilliance. That alone gets it on this list and the rest of it maintains a solid quality even if it's a little outdated.
24. TRAINWRECK
Like the majority of people these days, I'm not a huge Amy Schumer fan. However, Trainwreck shocked me and a lot of the audience. Written by Schumer herself, this rom-com is legitimately funny. Larger-than-life celebrities like LeBron James (playing himself) and John Cena do hilarious work here early in their acting days with some raunchy humor that mostly hits. SNL album Bill Hader also breaks out in a big way in this one thanks to his surprisingly good chemistry opposite Schumer, which is obviously one of the most important ingredients of any romantic comedy.
23. FORCE MAJUERE
Next, we have an international movie that you have probably never heard of. While yes, they did make an American reboot called Downhill with Will Ferell but honestly the less said about that half-assed work the better. Because of that, I'll give y'all a quick rundown of this film. A Swedish family goes on vacation in the French Alps, but when an avalanche hits them, the father abandons his kids and family whereas the mother does not. That creates an uncomfortable rest of the trip considering how men/parents are generally supposed to put their kids over themselves and now it's this elephant in the room. Now I understand that this doesn't sound very comedic, and yeah it's not overly funny but it's a great character study on marriage even if it can be a little slow at times.
22. CRAZY, STUPID LOVE
Crazy, Stupid love has one of, if not the most prestigious cast on this list. Steve Carell, Ryan Gosling, Emma Stone, Julianne Moore, and Kevin Bacon are just five of the actors that make up the bunch and they all give charming performances for this one. The scene where all the secrets break loose at the party is the standout and one of the classic scenes from any-rom com is thanks to the chemistry of said cast.
21. LOVE, SIMON
There's been a large uptick in LGBTQIA+ movies recently with the releases of films like Bros and Call Me By Your Name, mainly thanks to woke culture and the increased acceptance of the community. Sadly, not many have made a dent quite like Love, Simon. This novel adaptation was so popular it spawned a spinoff TV show called Love, Victor on Hulu. This coming-of-age movie is a raw and authentic depiction of what it's like growing up in high school in the closet. Love, Simon might make you tear up or it might make you laugh out of the hilarious awkwardness of Simon's coming out to the family scene that never gets old.
20. JERRY MAGUIRE
"Show me the money!" Jerry Maguire is endlessly quotable and while you may not think of it as a "rom-com," I wouldn't classify it as a sports movie either. It's got a lot of drama and heart to go along with some a neat look into the world of sports business. Tom Cruise, of course, puts his all into this one and if you don't believe me that this is one of the best performances he's ever had, just ask The Academy (yes, he got a Best Actor nomination here). He works great with Renee Zellweger and Cuba Gooding Jr to make this as realistic and weirdly relatable as possible.
19. SET IT UP
Set it Up is one of the newer, more under-the-radar rom-coms here but a movie doesn't have to be some old-ass classic that doesn't hold up anymore to show up in the top 25, as the standard changes. Set It Up has a pretty basic premise of two underpaid assistants who set up their bosses together to make everybody involved less miserable. OF course, this is a Netflix original so you can kind of predict how it's gonna go. When reading this you probably aren't jumping for joy, but it's a cliche movie that does everything well, from being relatable, entertaining, simple, fun, and consists of fantastic chemistry all around. It also benefits from Glenn Powell’s surge in popularity lately.
18. HER
In a ranking containing a movie about a mermaid falling in love with a human (we'll get to that soon), Her still might be the most bizarre film on this page. Whereas that is obviously a fantasy film in a grounded world, Her is a movie that the director Spike Jonze believes could conceivably happen in our near future. That is, to fall in love with an operating system. It sadly deals with the human need for connection and desperation to not be alone. It can be a depressing tale at times, but the intrigue of the premise never fails to keep you entertained and is executed perfectly.
17. SPLASH!
While the whole fish out of water story was popularized by The Little Mermaid many years ago, this was the first live-action movie to really get it right. Tom Hanks as the male romantic lead was a bold play at the time believe it or not, but he effortlessly slides into this strange role with the always funny John Candy at his side. On paper, this shouldn't work but it makes for a weirdly enjoyable ride thanks to its innocence and charm. It also doesn't that they have a couple of iconic songs in it to go along with the beauty of Darryl Hannah.
16. 13 GOING ON 30
13 Going on 30 is a light-hearted and simple movie that tackles the transition to adulthood. Jennifer Gardner nails the whole kid in an adult body shtick by knowing exactly what type of movie she was in. Her and Mark Ruffalo's characters make for a cute duo in a movie that has a fun time telling its story. This allows for it to be an easily rewatchable movie in a way that not many of these other films can match. While it doesn't get too deep it has nice messages about truly finding yourself as you get older yet at the same time appreciating your youth.
15. PUNCH-DRUNK LOVE
Whereas 13 Going on 30 takes on a light tone, Punch-Drunk Love may be the opposite. This is your writer's favorite Paul Thomas Anderson film for a myriad of reasons. It's an exploration of the stages of love, including the feeling of loneliness before you find it, the chaotic nature in the beginning stages, and the comfort that comes after everything starts to fully click. This movie is also not at all what you would expect from Adam Sandler, who is completely out of his comfort zone here. Luckily, he knocks it out of the park as the socially awkward Barry. Last but not least, if you're a fan of symbolism, the use of colors in this film should be studied and truly makes Punch-Drunk Love special.
14. LEGALLY BLONDE
Legally Blonde surpasses many of the other sillier films on this list for being goofy while being smart, if that makes sense. Similar to Dumb and Dumber, it uses stupid humor in ironic ways that hit the mark more often than not. It also doesn't hurt when you have Reese Witherspoon cast perfectly in the role so much so that it spawned a sequel. She's someone to root for as a hard-working yet sometimes naive girly girl that everyone thinks is outside of her element when in fact it may be themselves that they should be judging.
13. BRIDESMAIDS
While this doesn't revolve around one relationship rather than a group of them, it more than makes up for it with the stellar, hysterical cast including a best supporting actress nominee turned by a peak Melissa Mccarthy. If you haven't seen the food poisoning scene, you are seriously missing out. Luckily, everyone else involved here is also bringing their all to this comedy by allowing themselves to be embarrassing as hell on the big screen.
12. 40 YEAR OLD VIRGIN
The 40-Year-Old Virgin has maybe the best physical comedy of any rom-com here. Steve Carell was killing the game at this point in his career, but this is where he really blew up. This film is all about sex and the social intricacies that surround it. Half of this movie is improved, and while that can go wrong at times (looking at you Thor: Love and Thunder), it pays off here. For example, all the reactions to Steve Carell ACTUALLY getting the hair around his nipples waxed is all genuine stuff.
11. 10 THINGS I HATE ABOUT YOU
The whole opposites attract concept is one of the traits that makes 10 Things I Hate About You so great. Yes, it has been done many times but here it is really believable I always like to root for these types of couples and the writing is sharp enough to make this special. There are iconic moments that a classic rom-com should have like the “Can’t Take my Eyes Off of You” serenade and the final reading of the poem too. RIP Heath.
10. HOW TO LOSE A GUY IN 10 DAYS
Matthew McConaughey used to be every romantic comedy not so long ago and How to Lose a Guy in 10 days has to be his best. He and Kate Hudson effortlessly bounce off each other to make this movie work so effectively. It’s very funny and oddly relatable as well. They’re very charming and makes for a light and very rewatchable movie.
9. SOMEONE GREAT
Someone great has yet to get the respect it deserves from the community but that’s likely due to it dropping on Netflix without much fanfare. That’s a shame because it’s a sleeper hit exploring a bunch of different complex relationships among the main trio. Most of the rom-coms that are great end happily ever after but I feel like this an accurate modern and grounded depiction of what dating is actually like today. This change of pace help it stand out against the rest.
8. LA LA LAND
La La Land may be much higher for some people and considering the award attention it got when it came out that is completely justified. I loved seeing it the first time despite the unanimous praise possibly skewing my view. It’s just hard for me to say it’s better than the ones below. The production values are some of the best for any movie in general. Specifically, the choreography, cinematography, direction, and performances are phenomenal throughout although I just found the characters to be someone one-dimensional.
7. SILVER LININGS PLAYBOOK
Another movie with was met with critical claim is silver Linings Playbook. The script and its blunt dialogue is my favorite part of this movie. Some of the things they say are just ridiculous to hear but in a good way. Director David O. Russell incorporated so much of Philadelphia’s culture with their sports fandom, the tough love, and loyalty that add layers of meaning to the central relationship. I don’t know many pictures that can successfully weave themes like that so well. You don’t even need to be an eagles fan to enjoy Silver Linings Playbook!
6. WHEN HARRY MET SALLY
Straying away from Oscar nominees now, we have what is known as the quintessential romanic comedy. When Harry Met Sally is the most well-rounded rom-com. There is a brilliant script balancing many topics like gender dynamics and friendship while adding plenty of humor and love into it as well. Billy Crystal and Meg Ryan also have exceptional chemistry lifting this movie up. they also give us many memorable moments and quotable lines like “I’ll have what she’s having”. I't’s THE classic.
5. CLUELESS
Clueless is an iconic film build around a character who wants to be seen as that. Cher (Alicia Silverstone) is a stylish and superficial person that we get to see develop into an adult. It also doesn’t follow the typical rom-com formula, in that the love interest (a very young Paul Rudd) doesn’t really show up as. thought to her or the audience until late the movie. The focus on Cher needing to grow up has to take center stage first and I thought that was a cool way to tell the story.
4. THE BIG SICK
Standing out as easily one of the more original screenplays and plots on this list, this Oscar-nominated comedy arguably contains the funniest script of the bunch and doesn't need unpredictable and wacky moments to be that way. Therein lies the charm of The Big Sick, thanks to Kumain Najiani who pulls double duty here as the writer and star of this vehicle and absolutely crushes it. There are many laugh-out-loud moments that take place that doesn't take away from the serious nature of what happens halfway through the movie with his partner's sickness. It’s an absolute no-brainer for the top 5.
3. ABOUT TIME
As is becoming a theme on this page, we have another modern masterpiece. While this may be because of this writer's youth, many of the older rom-coms have become outdated and don't explore many deep topics while also not being as clever. And speaking of clever, this witty movie surrounding a family that can time-travel is truly a beautiful film that delves into the importance of family, love, and (you guessed it) time. It's all about appreciating the little everyday things with the people you care about and learning to live with the fact that not everything needs to be perfect all the time. It'll get your emotions moving in the best ways and the only thing keeping this from the top spot is the arguably manipulative manner of the time-travel execution that means it isn't as satisfying of a love story.
2. THE GRADUATE
Alright, time to bring things back about 50 years with the still-discussed and popular Dustin Hoffman film. The Graduate has already had so much said about it in this large time range, so I'll keep it brief. For starters, it contains one of the best uses of a song in a rom-com, or quite frankly any genre when it to the application of The Sound of Silence by Simon and Garfunkel. It's played three times to perfection which encapsulates the feelings and mood of the main character Ben, who has lost his way recently, and at these particular times in the movie. The Graduate explores finding one's purpose in life through dark comedy delivered through dry deliveries and quick, awkward moments/movements. For a film this old, you would think it would lose relevancy, but it may be one of those ageless wonders.
PALM SPRINGS
Recency bias is admittedly apparent with this one, but I think time will do wonders for how people appreciate its greatness. Palm Springs takes the Groundhog Day formula that has been done to death and modernizes it to make it feel warranted here. This movie is a riot of fun between two characters who stopped giving a damn due to the circumstances and allowed the actors to feel down-to-earth and endlessly relatable. The charming duo of Andy Samberg and Cristin Miloti become unhinged at moments that allow for hilarious out-of-pocket moments throughout. It also balances this humor with deeper themes such as feeling endlessly trapped and having to find happiness however you can. Therefore, Palm Springs rounds out this list as a classic that has yet to be deemed a classic by the general audience.
