The Best Romantic Comedies of All Time
To All the Boys: P.S. I Still Love You
Of course one must watch Rom Coms on Valentine’s Day! What else would we do?
There’s nothing worse than starting a Rom-Com, hoping to get some butterflies vicariously, and having the movie suck. The emotional letdown and the precious Netflix time wasted is a dead awful combo.
With that in mind, here are my favorite romantic comedies of all time, so you don’t make the mistake of putting the wrong Rom-Com on. Get yourself a glass of wine and get prepared to have a fabulous time with any of these wonderfully corny movies.
1. Roman Holiday (1953)
If you’ve never watched Roman Holiday… first of all, please don’t tell me. Second of all, please watch it before I find out that you haven’t. This is not only one of my favorite Rom-Coms of all time, but it’s simply one of my favorite movies of all time. Maybe it’s because of Audrey Hepburn, maybe it’s that it’s filmed in Rome, or maybe it’s Gregory Peck’s irresistible face, this movie always makes me smile from the heart.
Overwhelmed by her suffocating schedule touring Europe, Princess Ann (Audrey Hepburn) takes off for a night while in Rome. When a sedative she took from her doctor kicks in, however, she falls asleep on a park bench and is found by an American reporter, Joe Bradley (Gregory Peck), who takes her back to his apartment for safety. At work the next morning, Joe finds out Ann's regal identity and bets his editor he can get an exclusive interview with her, but romance soon gets in the way.
Fun Fact: The iconic scene that takes place at the Mouth of Truth, where Joe pretends his hand has been bitten off, was improvised by Gregory Peck. Audrey Hepburn wasn’t expecting it, so her terrified reaction is actually genuine!
2. To All The Boys I Loved Before, I, II, III (2018)
One might argue that I should have outgrown these types of Rom-Coms already, but no, I haven’t. I haven’t by the slightest. I can’t get enough of To All The Boys I Loved Before! Based on the trilogy novels of the same name, teenager Lara Jean Song-Covey writes 5 love letters that accidentally gets sent. What could go wrong? I love me the age-old plot of:
Shy girl likes popular jock. Jock turns out to be a super nice guy. Jock begins to fall for shy girl too. Misunderstandings happen. Shy girl doesn’t think jock is sincere. Jock is actually totally sincere. Misunderstandings get cleared up. They live happily ever after in high school.
I gobble this stuff right up!
3. Runaway Bride (1999)
You can’t have a “Best Rom-Coms of All Time” list without Julia Roberts movies. Of all her amazing Rom-Coms, the Runaway Bride is my favorite one.
Having already left three grooms at the altar, Maggie Carpenter (Julia Roberts) is branded "the runaway bride" by jaded city journalist Ike Graham (Richard Gere). After his article’s facts are called into question, Ike races to Maggie's hometown to save his reputation and report on her upcoming fourth trip down the aisle, during which he's convinced she'll run again. Though he's there on a muckraking mission, Ike can't help but fall for this breathtaking heartbreaker.
I love all the fights she has with Richard Gere throughout the movie, which seem like fights on the surface, but we all know it’s just them falling in love.
Without ruining the ending, I also love that scene on the balcony at the end. It’s just one of the best lines ever written about love! A must, must, must watch.
4. What A Girl Wants (2003)
Is there anyone else out there that misses movies like What A Girl Wants? On a whim, American teenager Daphne (Amanda Bynes) boards a plane to England to find her long lost father. She soon finds him, and also finds out that he is in fact Lord Henry Dashwood (Colin Firth), a member of the British upper class who is running for political office. Can this American girl survive in this new world?
Oh, how I miss the over-dramatic acting, the evil stepmother character, and the hot guy that rides a motorcycle. These types of movies were my whole childhood!
It was a close call between this movie and She’s the Man (another great Rom-Com by Amanda Bynes that also features young Channing Tatum), but I love the element of family in this movie as well. This movie definitely tugs on my heartstrings in more beautiful ways than one.
5. Sweet Home Alabama (2002)
In Sweet Home Alabama, New York fashion designer Melanie (Reese Witherspoon) finds herself engaged to the city's most eligible bachelor (Patrick Dempsey), but there’s only one problem, Melanie is already married to her high school sweetheart (Josh Lucas) who refuses to sign divorce papers. Bound and determined to end their relationship once and for all so she can get legally married to her new fiancé, Melanie sneaks back home to Alabama to confront her past, only to discover that you can take the girl out of Alabama, but you can't take Alabama out of the girl.
If you haven’t guessed already, Reese is expected to pick between Josh and Patrick to live happily ever after. What would you do? Who would you pick?
Could there be a more impossible task?! In my opinion, the casting director deserves a metal here. Oh, and there is a kissing scene in the rain, so the screenwriter deserves a metal, too.
6. The Philadelphia Story (1940)
This classic Rom-Com focuses on Tracy Lord (Katharine Hepburn), a Philadelphia socialite who has split from her husband, C.K. Dexter Haven (Cary Grant) because his drinking and her overly demanding personality. As Tracy prepares to wed again, this time to the wealthy George Kittredge (John Howard), she crosses paths with both her ex-husband Dexter as well as the prying reporter Macaulay Connor (James Stewart). Unclear about her feelings for all 3 men, Tracy must figure out whom she truly loves.
I didn’t end up watching this movie until last year (when being in quarantine forced me to watch an excessive amount of movies) because I wasn’t sure if I would love something filmed in the 40s. To my surprise, I absolutely adored it. Katherine Hepburn is brilliantly hilarious in this movie. In a way, her character in The Philadelphia Story reminds me of Rachel from Friends.
You don’t think you’re going to like her much in the beginning, but by the end of the movie, you will suddenly realize how much you’ve fallen in love with the character.
7. Holidate (2020)
For me, Holidate is the best Rom-Com made in recent years. Fed up with being single on holidays, two strangers agree to be each other's platonic plus-ones all year long, only to catch real feelings along the way.
This movie is legit funny. Like, I am in tears laughing and my abs actually hurt. It’s also legit romantic! Like, butterflies in my stomach, screaming “kiss her alreadyyyy” at the TV.
There’s also something about when the audience knows that the boy and girl feel something for each other, but they themselves don’t know, am I right?! You never get bored, even for a second, with a movie like this.
8. The Proposal (2009)
The Proposal is my favorite Sandra Bullock Rom-Com. Faced with deportation to her native Canada, high-powered book editor Margaret Tate (Sandra Bullock) pretends to be engaged to her hapless assistant Andrew Paxton (Ryan Reynolds) to stay in the country. Andrew agrees to the charade, but imposes a few conditions of his own, including flying to Alaska together to meet his eccentric family. With a suspicious immigration official always lurking nearby, Margaret and Andrew must stick to their fake wedding plan despite numerous mishaps. I love watching her and Ryan Reynolds slowly fall in love, especially when they can’t be more opposite.
There’s something so satisfying about watching two people that absolutely hate each other at the beginning of the movie come together as one in the end.
Unlike some other Rom-Coms, the characters in this movie are actually relatable (i.e. Ryan Reynolds’s strained relationship with his father) as people. I love that Betty White is the grandma in this movie; that scene in the woods between Sandra Bullock and Betty White is pure gold!
9. Pretty Woman (1990)
A movie that needs no introduction. A forever classic. I can watch Pretty Woman over and over again. In this modern update on Cinderella, a prostitute (Julia Roberts), and a wealthy businessman (Richard Gere) fall in love with each other. After Edward hires Vivian to stay with him for the weekend, the two get closer, only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.
Julia Robert’s perfect smile. Richard Gere’s hair. The fabulous fashion. The scene with the escargot. The “big mistake” scene. The scene on the piano. Need I say more?!
10. About Time (2013)
Of all the Rom-Coms on the list, About Time is always the one that makes me cry the hardest. When Tim Lake (Domhnall Gleeson) turns 21, his father (Bill Nighy) lets him in on the big family secret: The men in their family can travel through time. He meets Mary (Rachel McAdams), falls in love, and finally wins her heart via time-travel. However, as his unusual life progresses, Tim finds that his special ability can't shield him and those he loves from the problems of ordinary life.
In addition to watching a young couple fall in love, this is also a movie about a really special father and son relationship. Again, I think it’s the added element of a family that really brings these Rom-Com movies together.
You also can’t help but root for the nerdy guy to get the girl! He’s so awkward, but he loves her so much, and you just want her to see what you see!
11. Sabrina (1954)
Sabrina, another Audrey Hepburn classic. Sabrina (Audrey Hepburn), a chauffeur's daughter, returns home from Paris and immediately catches the attention of David (William Holden), the playboy son of her father's rich employer. David woos and wins Sabrina, who has always been in love with him growing up. However, their romance is threatened by David's more serious and older brother Linus (Humphrey Bogart), who runs the family business and is relying on David to marry an heiress for a crucial business merger to happen. The glamour, the fashion, and her fabulous haircut. It’s all so pleasing to the eyes!
One of the thing I love most about this movie is Sabrina’s internal growth. As cliché as the whole thing is, she grows from a girl that was ready to end her life over a boy she’s never even spoken to, to a woman that realizes the true meaning of love and the type of man she wants to be with. Just gotta love a plotline like that!
12. Something’s Gotta Give (2003)
This is another Rom-Com that makes me smile from ear-to-ear the whole time. When aging womanizer Harry Sanborn (Jack Nicholson) and his young girlfriend, Marin (Amanda Peet), arrive at her family's beach house in the Hamptons, they find that her mother, dramatist Erica Barry (Diane Keaton), also plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack, and a doctor (Keanu Reeves) prescribes bed rest at the Barry home, he finds himself falling for Erica , who, for once, may be out of his league.
Diane Keaton is so funny in Something’s Gotta Give, it makes me wish I was friends with her character.
One of my favorite scenes from the movie is when she’s completely heartbroken, hating herself for letting it happen in the first place, and going through boxes and boxes of tissue paper, and crying like a crazy person.
Have we all not experienced something like that? It’s so damn real that it’s freaking hilarious (especially when it’s happening to someone else on TV).
13. Notting Hill (1999)
Hugh Grant and Julia Roberts! I love this pair almost as much as I love Richard Gere and Julia Roberts! There are so many great moments in this movie because of how love-struck he is with Julia’s character, and it’s absolutely wonderful to watch.
William Thacker (Hugh Grant) is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when the famous American actress Anna Scott (Julia Roberts) appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.
Similar to About Time, you can’t help but cheer for the nerdy guy to win the heart of the amazing Julia Roberts that’s so obviously out of his league in Notting Hill. Get your girl Hugh, get your girl!!
14. Bridget Jones’ Baby (2016)
Of the three Bridget Jones movies, the third and last installment Bridget Jones’ Baby is my favorite. Breaking up with Mark Darcy (Colin Firth) leaves Bridget Jones (Renée Zellweger) over 40 and single again. Feeling that she has everything under control, Jones decides to focus on her career as a top news producer. Suddenly, her love life comes back from the dead when she meets a dashing and handsome American named Jack (Patrick Dempsey). Things couldn't be better, until Bridget discovers that she is pregnant. Now, the befuddled mom-to-be must figure out if the proud papa is Mark or Jack.
This is my favorite Bridget Jones movie because we see Bridget a bit more sure of herself in this one, and it’s so satisfying to watch! She’s finally outgrown Daniel Cleaver/Hugh Grant!
With that said, she’s still the same old funny Bridget who needs more help than she recognizes, which of-course makes a great Rom-Com.
15. Love, Simon (2018)
Everyone deserves a great love story, but for 17-year-old Simon Spier, it's a little more complicated. He hasn't told his family or friends that he's gay, and he doesn't know the identity of the anonymous classmate that he's fallen for online. Resolving both issues proves hilarious, terrifying and life-changing.
Rom-Coms in high school settings are the best because you know the struggle is real, and you know it! The stress of having sent a text when you didn’t mean to hit “send,” the process of stalking someone online, or trying to act cool in front of someone you like at a party.
You feel, in your core, the highs and lows of these characters as they are happening on screen, because you’ve been through the exact same things!
16. Leap Year (2010)
I am completely obsessed with Matthew Goode, so I might be slightly biased when it comes to Leap Year. When yet another anniversary passes without a marriage proposal from her boyfriend, Anna (Amy Adams) decides to take action into her own hands. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her lover to Dublin and ask him to marry her. However, Anna winds up on the other side of the Emerald Isle with the handsome but surly Declan (Matthew Goode), who may just lead Anna down the road to true love.
For me, the most unrealistic thing about this movie is how long Amy Adams was able to resist the perfection that is Matthew Goode!! If it were me… well, this movie would end 5 minutes in.
I also love these movies where a city girl goes to the country and is completely out of place. She’s struggles, then struggles some more. The guy, on the other hand, first finds her struggle to be outrageous, but eventually begins to see how cute she is in those moments of disaster. Dare I say true love?
17. Just Wright (2010)
I love a good Queen Latifah movie, because they aren’t just funny, they are also super feel-good. hysical therapist Leslie Wright (Queen Latifah) lands the dream job of working with basketball superstar Scott McKnight (Common). All goes well until Leslie finds that she is falling in love with him. Scott, however, is oblivious to Leslie's romantic overtures and focuses his attention on Morgan (Paula Patton), Leslie's gorgeous friend, who would love to be the basketball player's trophy wife.
With Just Wright, you not only get to experience all the butterflies of two people falling in love during a Rom-Com, you also get the feel-good at the end of the movie when she stands up for herself and asks for what she deserves.
The woman gets everything she’s ever wanted in the end, in both her professional and personal life, because she’s someone that’s beautiful inside and out. Can we all say #bossbabe?
18. The Wedding Date (2004)
With the wedding of her younger sister (Amy Adams) fast approaching, Kat Ellis (Debra Messing) faces the undesirable prospect of traveling alone to London for the occasion. To make things worse, the groom’s best man is her ex that left her after years of dating. Determined to show everyone, including her ex, that her romantic life is as full and thrilling as ever, Kat hires a charming male escort (Dermot Mulroney) as her date.
I love, love, love Dermot Mulroney, who plays the male lead in this movie (he’s also in My Best Friend’s Wedding with Julia Roberts). Why he falls in love with Debra Messing in The Wedding Date is beyond me (because he deserves the actual world), but nevertheless, I will enjoy the time I get to see him on screen.
