The Top 5 Rom-Coms Of All Time
ALYSSA'S TOP 5 ROM-COMS:
#1 Crazy, Stupid, Love (2011) is the GOAT of Rom Coms - here’s why:
1. A Realistic Take on Love
Unlike many rom-coms, Crazy, Stupid, Love doesn’t present love as perfect or easy. It explores heartbreak, mistakes, and the idea that love is messy but worth fighting for.
2. The Perfect Blend of Comedy and Emotion
The balance of humor and emotional depth is *chef’s kiss.* You get love, heartbreak, and self-discovery. The fight scene(!!!!) is chaotic and hilarious, and brilliantly ties all of the storylines together. The moment when Gosling’s character asks Stone’s character if he could tell her something “personal” still brings tears to my eyes.
3. Stellar Cast and Performances
Usually, I’m not a fan of ensemble casts. It’s too hard to get to know everybody enough to *really* care about their storyline. But Steve Carell and Ryan Gosling play off of each other SO well (remember the scene about the straw, “how would I know something so intimate, Cal,” and the makeover scene?!?!). And we get memorable performances from Julianne Moore, Emma Stone, Marisa Tomei (the parent-teacher conference scene!!), and Kevin Bacon. Plus, we get a really cute storyline about a lovestruck boy and his babysitter (who has a crush on Steve Carell’s character).
4. The Iconic Ryan Gosling & Emma Stone Chemistry
The” Dirty Dancing" lift scene. Need I say more? #ItsLikeYourePhotoshopped
#2 Sleeping With Other People (2015) is insanely underrated:
1. A Love Story Rooted in Friendship
Rather than a typical love-at-first-sight scenario, Jake and Lainey’s relationship is built on friendship, trust, and shared experiences, making their romance feel more meaningful.
2. Witty and Smart Dialogue
The script is filled with clever, fast-paced banter. The humor is often self-aware, and avoids the clichés of typical rom-coms.
3. A Realistic Portrayal of Modern Dating
The film tackles themes like infidelity, emotional unavailability, and the struggle to maintain platonic friendships. It feels honest and relatable, rather than forced or overly dramatic.
4. The “Bottle Scene”
If you’ve seen it, this is probably the scene you remember most vividly. Jake teaches Lainey how to… well, properly open a bottle. It’s sexy, funny, and filled with unspoken tension.
#3 Hitch (2005) is still a gem:
1. A Unique Premise
A professional dating consultant who helps men improve their romantic lives? That’s already fresh and entertaining. But the twist is even better: Hitch himself struggles to play it cool when he falls in love (the liquid Benadryl scene after Hitch had shellfish!!).
2. The Lovable Underdog
Kevin James as Albert is a major highlight. His awkward (yet sincere) attempts to win over Allegra (Amber Valletta) provide some of the funniest and most memorable moments. (His dance scene!! #WeDontNeedPizza #TheyGotFoodAtTheParty)
3. The Message About Being Yourself
At its core, Hitch teaches that love isn’t about tricks or strategies—it’s about authenticity. The movie encourages people to be themselves, rather than trying to impress others with artificial confidence.
4. A Feel-Good, Satisfying Ending
The ending feels earned and uplifting. We’re left a little more optimistic about love and relationships.
#4 While You Were Sleeping (1995) was one of the movies that shaped my idea of what a rom-com should be:
1. The Mistaken Identity Plot
The mistaken identity premise—where Lucy (Sandra Bullock) is believed to be the fiancée of a man in a coma—creates a mix of humor that’s engaging and unpredictable.
2. The Lovable Supporting Cast
Lucy’s adopted "family," the Callaghans, is one of the best parts of the movie. They are quirky, warm, and hilarious, adding depth and humor to the story. Glynis Johns as Grandma Elsie is especially delightful. (Oh, the goldmine of one-liners!!) Plus, Lucy finally finds the love and family she has longed for.
3. Iconic and Hilarious Scenes
From the "leaning" conversation between Lucy and Jack, to “it’s not good for the baby,” to the chaotic family dinner scenes, the film is filled with memorable and quotable moments.
#5 How to Lose a Guy in 10 Days (2003) is a classic rom-com:
1. The Perfect Chemistry Between Kate Hudson & Matthew McConaughey
Kate Hudson (Andie) and Matthew McConaughey (Ben) have electric on-screen chemistry, making their love-hate relationship both hilarious and swoon-worthy. Their banter and comedic timing are spot-on.
2. A Unique and Entertaining Premise
The movie flips the typical rom-com formula by having both leads secretly trying to manipulate each other—Andie is trying to drive Ben away for a “story,” while Ben is trying to make her fall in love with him to win a bet (as you may know, Dave and I love to write about bets). This creates endless comedic tension.
3. Hilarious Over-the-Top Antics
From Andie naming Ben’s… private parts to forcing him to sit through a Celine Dion concert, her exaggerated attempts to be the "worst girlfriend ever" are laugh-out-loud funny.
4. The Supporting Cast Adds Extra Humor
Let’s just take a moment for the Love Fern…
5. The “You're So Vain” Karaoke Scene
This is the scene when Andie and Ben’s fake relationship starts to crack under real emotions. Their playful singing turns into a heated, jealousy-fueled argument, making it one of the most pivotal moments in the film.
6. The Classic Rom-Com Tropes Done Right
The movie embraces rom-com clichés—fake dating, misunderstandings, grand gestures—but somehow executes them in a fun and original way. By the end, we are cheering for Ben to get the girl!!
DAVE'S TOP 5 ROM-COMS:
NOTE FROM DAVE: I am intimidated by how well Alyssa reviewed these films. Will be checking ancestry websites after I write this to see if she's related to Siskel or Ebert. =)
Let's dig into mine.
#1: Sleeping With Other People (2015), a movie Jason Sudeikis was shocked that I asked about.
Sudeikis is one of many Hollywood gems from Alyssa and I's hometown of Kansas City. Once a year, there's an event we work together, along with Paul Rudd, Eric Stonestreet, Rob Riggle and dozens of others.
The most recent time I spoke with Sudeikis, he was shocked that I wanted to delve into “Sleeping With Other People” and NOT “Ted Lasso.” I think I gained respect. Haha.
I'm not writing this to brag, but rather to mention that he himself LOVED this project and gushed about everyone involved with it – never taking any credit. He should, though, because he and Alison Brie are PERFECT in their cast roles.
If you haven't seen this film, you MUST. As Alyssa notes above, it's a story of love via friendship and the hilarious but struggle of finding that balance. It's “real life” but a heck of a whole lot funnier.
I love various “mouse trap” scenes, the “Dirty DJ” and the sex addicts anonymous scene toward the beginning of the film.
A must see and I'm glad Alyssa and I agree on this banger.
#2: Notting Hill (1999) will never NOT be a Top 5 Rom-Com – and #ThatSoundtrack
Hugh Grant and Julia Roberts are so great together in this film about an “Average Joe” who runs a travel bookstore in Notting Hill, and a movie star who happens to come into the shop.
The screenplay in this one by Richard Curtis depicts vulnerability of not only love, but insecurities – PERFECTLY. This film works because of the hilarity of Grant and his flat mate, in particular – but also because it really is a deep dive into how a famous person has the same struggles as a “peasant,” so to speak.
Also, can we talk about this soundtrack? It's full of bops.
98 Degrees, Boy Zone, Ronan Keating, Elvis Costello, etc.
#3: Serendipity (2001) is a love masterpiece
I can't tell you how often I bring this movie up to fellow Rom-Com aficionados and they BEAM with excitement. I swear that this film has a cult following and even though it's not really a traditional Rom-Com (it's more of a sappy love story), it has funny parts and I'm classifying it as such.
John Cusack and Kate Beckinsale star alongside a supporting cast of Jeremy Piven, Molly Shannon, Eugene Levy and Bridget Moynahan in this story about finding chance love – SERENDIPITIOUS love.
In the vein of Notting Hill, both main characters are extremely vulnerable, especially Cusack, and I love that Beckinsale is such a free spirit. Jeremy Piven's obituary scene where he writes Cusack's fake death as a hopeless romantic is one of my favorite moments in movie history.
#4: That Awkward Moment (2014) is a bro Rom-Com – but still insanely sweet
I LOVE THE FREAKING CAST IN THIS MOVIE. Zac Efron and Imogen Poots are the stars – and soooo good together - but to me, Miles Teller, Mackenzie Davis and Michael B. Jordan are what MAKE this movie.
Tom Gormican wrote this funny film and I love the struggle he had in making it a reality, yet how he persevered. This was a film that was on “The Black List”forever – Gormican was told “it wouldn't work” and “wouldn't sell” - yet he eventually got it made and it was a big success.
Miles Teller in particular is hilarious and I find myself imagining him playing a character in one of Alyssa and I's screenplays someday. He's probably past the Rom-Com phase of his career, but a writing duo can dream, right?
#5: For Love of the Game (1999) is my all-time favorite movie and again, not a textbook Rom-Com – but it's going on this damn VERY scientific list =)
Kevin Costner. Kelly Preston. John C Reilly. Jena Malone.
I've seen this movie about love and baseball probably 50 times – and can quote pretty much the entire thing.
Costner (MLB pitcher) is driving through New York City in his rental when he sees Preston (magazine writer) broken down. They meet, stay in touch and the movie goes from current day to flashback over and over as he's (unknowingly to himself) about to throw a perfect game at Yankee Stadium while dealing with the heartbreak of their breakup.
You can't get anymore romantic than baseball.'
*** NOTE *** How did Alyssa and I write this without a SINGLE TOM HANKS/MEG RYAN movie?!??!?! We are SINNERS!!!