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Best Romantic Comedies of all Time

Marian K
This list of best romantic comedies of all time, is a compilation of movies that are lighthearted, funny and able to tug at your heartstrings. Here are some of my favorites...
Ten Things I Hate About You. Notting Hill. Moonstruck. You've Got Mail. The Philadelphia Story. Juno. Movies that have made audiences laugh, left them misty-eyed and even helped many fall in love.
That is the beauty of romantic comedies - they are not as tragic as other love stories. Sure, the plots have their ups and downs but not without a twist that ensures a laugh here and there. People love watching romantic comedies and the following list names some of the unforgettable classics.

When Harry Met Sally...

Synopsis - Audiences fell in love with this amazing tale of two New Yorkers, Harry (Billy Crystal) and Sally (Meg Ryan) who believe that sharing physical intimacy could ruin their true friendship. Rob Reiner with his killer direction and amazing punchlines ensures that audiences are entertained right till the end.
Memorable Lines -

Sally Albright:
Well, if you must know, it was because he was very jealous, and I had these days of the week underpants.
Harry Burns: Ehhhh. I'm sorry. I need the judges ruling on this. "Days of the weeks underpants"?
Sally Albright: Yes. They had the days of the week on them, and I thought they were sort of funny. And then one day Sheldon says to me, "You never wear Sunday." It was all suspicious. Where was Sunday? Where had I left Sunday? And I told him, and he didn't believe me.
Harry Burns: What?
Sally Albright: They don't make Sunday.
Harry Burns: Why not?
Sally Albright: Because of God.

It Happened One Night

Synopsis - No List of romantic comedies can be completed without this flick. The story shows Ellen (Claudette Colbert), a rich socialite who runs off to remarry her fortune-hunter spouse and on the way meets an unemployed reporter Peter (Clark Gable) who becomes her uncanny companion in the journey.
This movie enthralled audiences and critics alike and won 5 Oscars. Though the movie was released almost seven decades ago, It Happened One Night is still magical to see.
Memorable Lines -

Ellie: Aren't you going to give me a little credit?
Peter: What for?
Ellie: Well, I proved once and for all that the limb is mightier than the thumb.
Peter: Why didn't you take off all your clothes? You could have stopped forty cars.
Ellie: Oh, I'll remember that when we need forty cars.

Annie Hall

Synopsis - Millions think that Vicky Christina Barcelona is Woody Allen's best work but I still feel that with Annie Hall, he struck pure gold. The movie shows Alvy Singer (Allen) a comedian trying to understand the failure of his relationship with Annie Hall (Diane Keaton).
Allen's genius direction brought Annie Hall four Oscars and made him and Keaton international celebrities.
Memorable Lines -

Alvy: It's all mental masturbation.
Annie: Oh, well, now we're finally getting to a subject you know something about.
Alvy: Hey, don't knock masturbation. It's sex with someone I love.

The 40 Year-Old Virgin

Synopsis - You've probably guessed it with the name --- Andy Stitzer (Steve Carell) is a middle-aged electronic store salesman who has never done the deed and is surrounded by friends who ensure that he gets deflowered. The amazing chemistry that Carell shares with his co-workers is the main highlight of the movie.
Memorable Lines -

Ebay store customer: So, I guess I'll just give you some money, and you can give me these shoes and--
Trish: You know, I know it seems so strange--
Ebay store customer: Yes. I'd just rather buy them from you straight up.
Trish: Yeah, I know. I wish it could be that easy, but--
Ebay store customer: I wish, too, but you're making it extremely difficult for me. I'm just trying to get these shoes back to my house so I can wear them.

Pretty Woman

Synopsis - Still considered as one of the best romantic comedies of all time, Pretty Woman is must watch for everyone. The movie is about a hooker falling for her client. Vivian Ward (Roberts) is a hooker with a heart of gold who is hired by millionaire businessman Edward Lewis (Gere) to be his escort for a week.
This movie is still considered the most popular option in the romance comedy genre and gathered a Golden Globe and an Oscar nomination.
Memorable Lines -

Edward: Any questions?
Vivian: Can I call you Eddie?
Edward: Not if you expect me to answer.
Vivian: I would have stayed for two thousand.
Edward: I would have paid four. I'll see ya tonight.
Vivian: Baby, I'm gonna treat you so nice, you're never gonna wanna let me go.
Edward: Three thousand, for six days, and Vivian, I will let you go.

The Holiday

Synopsis - Two woman (Kate Winslet and Cameron Diaz) tired of love and men swap homes in each other's countries. The problem occurs when they each meet a local guy and fall hopelessly in love all over again. Supporting caste includes Jack Black and Jude Law. This film is filled with just the right amounts of love and humor that makes it so amazing.
Memorable Lines -

Iris: It doesn't matter how many new haircuts you get, or gyms you join, or how many glasses of chardonnay you drink with your girlfriends... you still go to bed every night going over every detail and wonder what you did wrong or how you could have misunderstood.
And how in the hell for that brief moment you could think that you were that happy. And sometimes you can even convince yourself that he'll see the light and show up at your door.
And after all that, however long all that may be, you'll go somewhere new. And you'll meet people who make you feel worthwhile again. And little pieces of your soul will finally come back. And all that fuzzy stuff, those years of your life that you wasted, that will eventually begin to fade.

Four Weddings and a Funeral

Synopsis - The plot is about Charles (Hugh Grant) a charming yet shy Englishman who falls for an attractive American woman Carrie (Andie MacDowell) whom he keeps on bumping at weddings and a funeral.
The movie is delightful and cleverly mixes up all the situations to make a loving comedy. It was the winner of four BAFTA awards and was also nominated for two Oscars.
Memorable Lines -

Charles: Let me ask you one thing. Do you think - after we've dried off, after we've spent lots more time together - you might agree not to marry me? And do you think not being married to me might may be something you could consider doing for the rest of your life?
Carrie: I do.

50 First Dates

Synopsis - A commitment phobic womanizer Henry Roth (Adam Sandler) meets the love of his life Lucy Whitmore (Drew Barrymore). They hit it off instantly and fall in love, the only problem is Lucy suffers from short term memory loss and forgets him the very next day. Though not universally acclaimed, it was one of the best movies of 2004 and a crowd favorite.
Memorable Lines -

Henry: Hah! I can't believe you fell for that!
Lucy: My grandfather died while trying to jump-start a car...
Henry: Oh...I'm so sorry...I was just joking around.
Lucy: I can't believe you fell for THAT! HA HA!

There's Something About Mary

Synopsis -A nerd (Ben Stiller) gets the opportunity to take his girl of dreams (Cameron Diaz) to prom but can't make it. Years later, he is still in love with her and hires a private detective (Matt Dillon) to track her down.
The detective falls in love with her and encounters another opportunist trying to win her affections. The movie was a surprise hit and is considered a cult classic today. It also got Stiller and Diaz instant stardom.
Memorable Lines -

Pat Healy: Really, it's only a side thing for my true passion.
Mary: And what's that?
Pat Healy: I work with retards.
Mary: Isn't that a little politically incorrect?
Pat Healy: Yeah, maybe, but hell, no one's gonna tell me who I can and can't work with.

Bridget Jones's Diary

Synopsis - Bridget Jones (Renee Zellweger) is a single frustrated woman who smokes, is accident prone and worries about her increasing weight. After a series of unfortunate incidents, she decides to turn things around and starts a new chapter.
Things take an interesting turn when two men Daniel (Hugh Grant) and Mark (Colin Firth) enter her life. It is considered Zellweger's finest performance and also got her an Oscar nomination.
Memorable Lines -

Daniel Cleaver: First, have some more wine, and then tell me the story about practicing French kissing with the art girls at school, because it's a very good story.
Bridget: It wasn't French kissing.
Daniel Cleaver: Don't care, make it up. That's an order, Jones.

Breakfast at Tiffany's

Synopsis - The story is about Holly Golightly (Audrey Hepburn) a New York socialite who lives a carefree lifestyle in an alone apartment. She dates rich men but never reciprocates their feelings due to her commitment phobic nature.
Her life takes a different turn when she meets her new neighbor Paul (George Peppard) who is suffering from a writer's block. The movie was nominated for several Oscars and cemented Hepburn's status as an ageless beauty.
Memorable Lines -

Holly: He's all right! Aren't you, cat? Poor cat! Poor slob! Poor slob without a name! The way I see it I haven't got the right to give him one. We don't belong to each other. We just took up one day by the river.
I don't want to own anything until I find a place where me and things go together. I'm not sure where that is but I know what it is like. It's like Tiffany's.
Paul: Tiffany's? You mean the jewelry store.
Holly: That's right. I'm just crazy about Tiffany's!

Wedding Crashers

Synopsis - John (Owen Wilson) and Jeremy (Vince Vaughn) are divorce mediators who often crash wedding parties to meet women. They follow a set of rules and are a delight to be with. Things get nasty when they crash a wedding reception and fall in love.
The plot is about their humorous attempts to win the hearts of the women they truly love. The movie was a huge hit with the audiences and gathered positive reviews from critics globally.
Memorable Lines -

Jeremy: I don't give a baker's fuck! I just had my own sock duct taped into my mouth last night!
John: Whoa, what?
Jeremy: Yeah, the, the sock that I wore all day, playing football in, pouring sweat in, was shoved into my mouth and then was duct taped over it!
John: Well, then let's talk about it. I'm a good listener.
Jeremy: I'm not going to discuss this. I felt like Jodie Foster in "The Accused" last night.

My Big Fat Greek Wedding

Synopsis - Toula Portokalos (Nia Vardalos) is the ideal Greek daughter and believes she was sent on earth for three reasons: to marry a Greek man, have Greek kids and feed everyone till she's alive. She is single, frustrated and looking out for a much-needed change which arrives in the form of Ian Miller (John Corbett).
The movie has gathered immense critical acclaim and Vardalos was nominated for an Academy for the best original screenplay.
Memorable Lines -

Gus: [to Toula] You better get married soon. You're starting to look... old!
Toula: [narrating] My dad has been saying that to me since I was fifteen. Because nice Greek girls are supposed to do three things in life: marry Greek boys, make Greek babies, and feed everyone until the day we die.


Synopsis - Sideways tells the story of Miles (Paul Giamatti), a recently divorced failed novelist, and his soon-to-be married friend Jack (Thomas Haden Church), a washed-up actor. To enjoy life to the fullest, the two men take one last road trip in the week before Jack's wedding.
An oenophile, Miles is determined to educate his friend on California's beloved Pinot Noir wines before the wedding. Jack appreciates his best friend's passion for wine but is mainly interested in having his last fling before walking down the aisle.
Trouble comes knocking when they meet two gorgeous women and gradually realize their own shortcomings and understand what life is really about. The movie was nominated for five Oscars and won for the best adapted screenplay.
Memorable Lines -

Miles Raymond: Let me show you how this is done. First thing, hold the glass up and examine the wine against the light. You're looking for color and clarity. Just, get a sense of it. OK? Uhh, thick? Thin? Watery? Syrupy? OK? Alright.
Now, tip it. What you're doing here is checking for color density as it thins out towards the rim. Uhh, that's gonna tell you how old it is, among other things. It's usually more important with reds. OK? Now, stick your nose in it. Don't be shy, really get your nose in there. Mmm... a little citrus... maybe some strawberry...
[smacks lips]
Miles Raymond: ... passion fruit...
[puts hand up to ear]
Miles Raymond: ... and, oh, there's just like the faintest soup├žon of like asparagus and just a flutter of a, like a, nutty Edam cheese...
Jack: Wow. Strawberries, yeah! Strawberries. Not the cheese...

Say Anything...

Synopsis - A cute practical teenage comedy about love. Diane Court (Ione Skye) plays a high-school valedictorian heading to England on a scholarship. Things get messy when she starts dating Lloyd Dobler (John Cusack), an underachiever army brat with a good heart.
When she breaks off the relationship due to her over-protective father, Lloyd spends the whole summer trying to win Diane's heart back. The movie was hailed as one of the best films of 1989 and made Cusack and Skye popular names.
Memorable Lines -

Diane Court: Are you shaking?
Lloyd Dobler: No.
Diane Court: You're shaking.
Lloyd Dobler: I don't think so.
Diane Court: You're cold.
Lloyd Dobler: I don't think I am.
Diane Court: Then why are you shaking?
Lloyd Dobler: I don't know. I think I'm happy.

Bull Durham

Synopsis - Bull Durham is the story of America's favorite pastime (baseball) with a little bit of love, jealousy and humor in it. Crash Davis (Kevin Costner) is a Minor League player assigned to train a hapless team. There he meets a young, foolish pitching prodigy, Nuke LaLoosh (Tim Robbins) and tutors him to become a pro.
Both hate each other and to complicate matters further, both strike up a romance with Annie (Susan Sarandon) the team's mascot who sleeps with a new player every season. The movie was very well-received globally and is also considered one of the best sports movies of all time.
Memorable Lines -

Ebby: [After he has challenged Crash to a fight] I don't hit no man first.
Crash Davis: All right, then... [throws him a baseball] ...hit me in the chest with that.
Ebby Calvin LaLoosh: I'd kill you!
Crash Davis: Yeah? From what I hear, you couldn't hit water if you fell out of a fucking boat. [the crowd that has gathered gawks] Come on; right here, right in the chest.
Ebby Calvin LaLoosh: No way!
Crash Davis: C'mon, Meat! Throw it! You know you're not gonna hit me, cause you've already started to think about it, eh? Thinkin' about how embarrassing it would be to miss in front of all these people, how somebody might laugh? Come on, 'rook, show us that million-dollar arm. 'Cause I got; oh yeah, I got a good idea about that five-cent head of yours.
[LaLoosh throws the ball and misses Crash by several feet, breaking a window]
Crash Davis: Ball four.
Ebby Calvin LaLoosh: Who the hell are you, man?!
[LaLoosh charges at Crash, who drops him with one punch to the face]
Ebby Calvin LaLoosh: Good punch...
Crash Davis: I'm Crash Davis; I'm your new catcher, and you just got lesson number one; Don't think. You can only hurt the ball club.

Knocked Up

Synopsis - Ben Stone (Seth Rogen) a pot smoking porn site developer meets the career driven and recently promoted Alison Scott (Katherine Heigl) at a bar. After a night of drinking and dancing, they end up spending the night together and Alison becomes pregnant.
Now, the overgrown kid Ben decides to take up the responsibility and supports Allison in every way he can. The movie is filled with sarcastically hilarious yet sweet instances depicting two opposite individuals falling in love and getting ready for parenthood.
Knocked Up was one of the most critically acclaimed movies of 2007 and was nominated for the Writers Guild of America Award for the Best Original Screenplay.
Memorable Lines -

Alison Scott: I'm pregnant.
Ben Stone: Fuck off!
Alison Scott: What?
Ben Stone: What?
Alison Scott: I'm pregnant.
Ben Stone: Pregnant... with emotion?
Alison Scott: Pregnant with a baby.

As Good As It Gets

Synopsis - It is a story of friendship and love between three unlikely people. Melvin Udall (Jack Nicholson) is a best-selling novelist suffering from obsessive compulsive disorder. Carol Connelly (Helen Hunt) is a single mother, waitress and the only one in New York capable to handle Udall's erratic temperament.
Simon Nye (Greg Kinnear), a gay talented contemporary artist and Melvin's neighbor. As Good As It Gets is a classic example of truly discovering oneself and understanding the need of friendship and love in life.
It was a commercial and critical success bagging the Oscars for Best Actor and Actress for Nicholson and Hunt and was nominated for several other categories.

Memorable Lines -

Melvin Udall: I've got a really great compliment for you, and it's true.
Carol Connelly: I'm so afraid you're about to say something awful.

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Melvin Udall: Don't be pessimistic, it's not your style. Okay, here I go: Clearly, a mistake. I've got this, what - ailment? My doctor, a shrink that I used to go to all the time, he says that in fifty or sixty percent of the cases, a pill really helps. I *hate* pills, very dangerous thing, pills.
Hate. I'm using the word "hate" here, about pills. Hate. My compliment is, that night when you came over and told me that you would never... all right, well, you were there, you know what you said. Well, my compliment to you is, the next morning, I started taking the pills.
Carol Connelly: I don't quite get how that's a compliment for me.
Melvin Udall: You make me want to be a better man.
Carol Connelly: ...That's maybe the best compliment of my life.
Melvin Udall: Well, maybe I overshot a little, because I was aiming at just enough to keep you from walking out.

Good Luck Chuck

Synopsis - Good Luck Chuck is the story of Charlie (Dane Cook) and his inability to find true love. Sure, he dated a lot and even had his fair share of flings but none of his relationships last and all the women who sleep with him end up marrying the next guy they meet.
He then meets Cam (Jessica Alba) an aquatic bird specialist at a wedding. To ensure that Cam doesn't end up marrying the next guy she meets, Charlie does everything in his power to ensure that they don't sleep together. Good Luck Chuck is not a critics favorite but is filled with hilarious situations and Alba's clumsy performance is delightful.
Memorable Lines -

Charlie: Stu, Cam. Cam, Stu
Stu: It's actually *Doctor* Stu. I'm a reconstructive surgeon. If anyone has an accident or was born with a deformity, I'm there to help.
Charlie: And by "deformity" he means small breasts.
Stu: He's just jealous because he has to clean plaque all day long while I'm out making the world a better place.

No Strings Attached

Synopsis - After an embarrassing drunken night, good friends Adam (Ashton Kutcher) and Emma (Natalie Portman) end up being physical. And to save their friendship and themselves from commitment, they sign an only physical no emotion pact.
At first this "Friends with Benefits" arrangement works fine for both but things get messy when Adam begins to have feelings for Emma, and a relationship is the last thing on her mind.
This puts a full-stop on their friendship and agreement which forces them to figure out their priorities. The movie received mixed reviews but was a commercial success with audiences particularly liking Kutcher and Portman.
Memorable Lines -

Emma: I made you a Valentine's Day card.
Adam: What?
Adam: It's perfect. Will you read it for me?
Emma: [reads card] You give me premature ventricular contractions.
Adam: I'm assuming that's a good thing.
Emma: You make my heart skip a beat.
Adam: Aww.
Emma: Don't make fun of me!

Crazy, Stupid, Love.

Synopsis - Cal Weaver (Steve Carell) is living the dream - a good job, great house, nice kids and a healthy marriage to his college sweetheart. But when his wife cheats on him and wants a divorce, his dream becomes a horrifying nightmare.
The worse part, he is 40, hasn't been on a date in decades and spends his evenings in a bar sulking. He quickly befriends Jacob Palmer (Ryan Gosling), a charming womanizer. Soon Jacob takes Cal as his wingman, teaches him everything about impressing women and tries to make him forget the past.
Though Cal loves the idea of a promising future, he just can't forget his ex-wife and tries everything to bring her back.

Memorable Lines -

Jacob: [looking at Cal's shoes] Are you Steve Jobs?
Cal: What?
Jacob: Are you the billionaire owner of Apple Computers?
Cal: No.
Jacob: Oh, OK. In that case, you've got no right to wear New Balance sneakers, ever.


Synopsis - Annie Walker (Kristen Wiig) is in her mid-30s, romantically unattached and a failed bakery owner who's only source of happiness is her BFF Lillian.
When Lillian (Maya Rudolph) announces her engagement and wants Annie to be her maid of honor, it drowns Annie into a sea of paranoia because she is broke and is about to lose her BFF. Her insanity increases when the rich and beautiful Helen (Rose Byrne) tries to assume control of all the wedding festivities, thereby sidelining Annie.
Though broke and frustrated, Annie tries to be happy for Lillian and does everything to ensure that her BFF gets the perfect wedding. Bridesmaids was Judd Apatow's most successful film and it was nominated for two Oscars.

Memorable Lines -

Helen: Oh Annie, these are my kids.
Girl: Step
Helen: [laughing] They are so hilarious! Excuse me, my husband's kids. What are you guys up to?
Girl: Going to the snack bar.
Helen: Awesome. You need a ride home later?
Boy: Fuck off Helen. [walks off]
Helen: Okay. Put a quarter in the swear jar. Good to see ya. [turns to Annie] So cute.
Annie: [nodding] Sweet kids.
Romantic comedies offer a bit of everything and are perfect for a date night. Though some of them are cheesy, they still manage to make the audiences laugh and put them in a good mood. Not all rom-coms could be included in this list. But, fret not. Please share the names of your favorite movies from this genre with us and let's see how long the list becomes. Happy movie-buffing!