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30 Best Classic Movies to Watch on Valentine's Day

Nov 17, 2020• Proven solutions

A nice dinner and a good movie can make for a perfect Valentine’s Day you and your significant other are going to remember for a long time. Hot popcorn, your favorite beverage, your beloved, a classic movie and a bit of cuddling; a Valentine’s Day cannot get any more romantic. Spending some ‘us’ time with a movie that you both love is a fitting way to celebrate Valentine’s Day in 2020.

Over a hundred years, countless romantic movies have amazed us, made us fall in love or reignited our passion for romance and have often compelled us to believe in love again when we had lost our faith.

It is almost impossible to compile a list that contains at least one classic movie from every era. Hence, we are going with 30 best classic movies to watch on Valentine’s Day in this year of 2020, given their popularity or universal appeal, originality and the messages they convey.

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30 Best Movies to Watch on Valentine’s Day [2020 List]

Depending on the TV channels you have when it comes to the selection of the movies you want to watch on Valentine’s Day can be a tricky choice since you may not be able to find the movie you would like to see. That is why you should turn to online streaming services like Netflix or Amazon prime in order to find the movie that is a perfect pick for the cozy evening you are going to spend with the person you love.

1. Titanic (1997)

IMDB Rating: 7.8/10

Directed by: James Cameron

Starring: Kate Winslet, Leonardo DiCaprio

Awards: 11 Oscars and 115 awards

Only three movies ever won 11 Oscars, and the fact that Titanic is one of them speaks volumes about the film’s status in the history of cinema. The movie follows the stories of Jack and Rose, who met each other and fell in love while traveling on Titanic just days before the ship sank. If you missed your chance to see this movie in the theaters, this Valentine’s Day may be the perfect opportunity for it.

Titanic has to be one of the greatest romantic movies of all time. The ill-fated couple, doomed from the very beginning, embarks on a whirlwind romance aboard the largest ship ever made (till 1912). Although it is not your typical love story and thus have a larger socioeconomic commentary apart from being a disaster movie, Titanic will remain a perennial favorite, perhaps forever. The movie didn’t just bring two of the finest actors of all time, Leo and Kate, but their chemistry was so indelible.

Touching Quotes:A woman's heart is a deep ocean of secrets. But now you all know there was a man named Jack Dawson, and that he saved me, in every way that a person can be saved.

Touching Quotes from Titanic

Image from Internet

2. Pretty Woman (1990)

IMDB Rating: 7.0/10

Directed by: Garry Marshall

Starring: Julia Roberts, Richard Gere

Awards: Won 8 awards

Pretty Woman is one of those more mushy romances with scant regard to reality but that is what fairytales are made of. Julia Roberts emerged as the star she was born to be and was aptly tagged as America’s sweetheart. It is not a path-breaking movie nor did it redefine the romance genre but it certainly made millions of people happy.

Chances are that you have already seen this movie since it is probably one of the most popular romantic comedies ever created. So, if you feel like walking down the memory lane, then rewatching Pretty Woman may be a great idea. Both Roberts and Gere are amazing in this movie, so there is a decent chance you’ll have more than a few good laughs.

The favorite quote: In c ase I forget to tell you later, I had a really good time tonight.

3. Gone with the Wind (1939)

IMDB Rating: 8.1/10

Directed by: Victor Fleming

Starring: Clark Gable, Vivien Leigh

Awards: Won 8 Oscars and 12 more awards

Gone with the Wind is an epic tale of romance at the height of the American Civil War and The Reconstruction Era. If the book is a literary masterpiece then the movie is a classic in itself. The acting of Clark Gable and Vivien Leigh would be enough to keep you hooked and then there are the amazing dialogues. The movie may be a tad too old for the millennial generation but it is never stale.

It tells the story about a tumultuous love affair. Gone with the Wind is probably one of the most famous love stories ever told on the big screen which makes it a perfect Valentine’s Day movie. Just don’t forget that the movie lasts almost four hours.

The favorite quote: After all, tomorrow is another day!

4. Jerry Maguire (1996)

IMDB Rating: 7.3/10

Directed by: Cameron Crowe

Starring: Tom Cruise, Renée Zellweger, Cuba Gooding Jr.

Awards: One Oscar and 25 awards

Yet another movie directed by Cameron Crow on our list that will make your Valentine’s Day a bit more special. At the very core, Jerry Maguire is a movie about the value of love and friendship that certainly won’t leave you indifferent. Besides, Cuba Gooding’s performance is phenomenal.

Jerry Maguire is a heartwarming tale of a young man falling in love with an older woman, who is also a single mother. Forever handsome Tom Cruise and always pretty Renee Zellweger come up with their sizzling chemistry and the pivotal plot of the movie is just beautiful. Then you have those famous one-liners that are still a hit among people falling in love.

The favorite quote: Shut up. Just shut up. You had me at hello.

5. The Notebook (2004)

IMDB Rating: 7.8/10

Directed by: Nick Cassavetes

Starring: Rachel McAdams, Gena Rowlands, Ryan Gosling

Awards: Won 12 awards

Love knows no social boundaries or does it? The Notebook is ranked as the most romantic movie of its times in most polls. It is undoubtedly a classic. The performances, the exotic rural romance and the climax that transformed the romance genre offer enough reasons to watch this classic on Valentine’s Day.

The Notebook is the movie that takes you on an emotional rollercoaster, as the story of a love torn apart by social differences unravels. The innovative structure of the movie and the excellent cast make every second of this movie worth seeing. You can watch The Notebook on Amazon Prime and other streaming services.

The favorite quote: So, it’s not gonna be easy. It is going to be really hard; we’re gonna have to work at this every day, but I want to do that because I want you. I want all of you, forever, every day.

6. Sleepless in Seattle (1993)

IMDB Rating: 6.8/10

Directed by: Nora Ephron

Starring: Mag Ryan, Tom Hanks

Awards: Won 4 awards

Sleepless in Seattle is one of the most unconventional romantic movies of all time. There is just one scene where the protagonists actually come together and there is hardly any words exchanged but the entire movie is a surreal ride of longing, desire and eventually finding love.

Rebounding from the loss of a loved one is always a slow and painful process. This 1993 classic explores what happens when you open to others and share with them how you feel. After hearing Sam’s story, Annie suggests that they should meet at the top of the Empire State Building on Valentine’s Day. Sleepless in Seattle is probably the ultimate Valentine’s Day movie on this list.

The favorite quote: They knew it. Time, distance, nothing could separate them. Because they knew. It was right. It was real.

7. Notting Hill (1999)

IMDB Rating: 7.1/10

Directed by: Roger Michell

Starring: Julia Roberts, Hugh Grant

Awards: Won 11 awards

Notting Hill was the highest-grossing British film of 1999 and a huge international success. The charming story of a love affair between a bookshop owner and a major Hollywood star is both entertaining and endearing as the couple manages to stay together despite all obstacles they have to face.

It brings together Hugh Grant and Julia Roberts as an unlikely pair. The movie is not very high on emotions but that is what a romantic comedy should ideally be. Great performances, an over the top climax and some really nice moments make for a satiating watch.

The favorite quote: After all... I'm just a girl, standing in front of a boy, asking him to love her.

8. Before Sunrise (1995)

IMDB Rating: 8.1/10

Directed by: Richard Linklater

Starring: Julie Delpy, Ethan Hawke

Awards: Silver Berlin Bear for Best Director

The first part of the trilogy, which also includes Before Sunset and Before Midnight, tells the story of how Jesse, a struggling writer who roams the street of Paris in search of inspiration and Celine a beautiful and incredibly smart girl met. If you don’t already know Linklater’s work Before Sunrise will certainly spark your interest and after watching it you’ll definitely want to see the remaining two parts of the trilogy.

Before Sunrise is a cult classic. It broke all stereotypes of romantic movies that existed then. The lovely landscape of Vienna, two interesting people at the height of their youth and endless talk about love and life eventually leading the two to fall in love only to part ways, that’s a lovely start to a Valentine’s Day at home.

The favorite quote: Listen, if somebody gave me the choice right now, of to never see you again or to marry you, alright, I would marry you, alright.

9. 50 First Dates (2004)

IMDB Rating: 6.8/10

Directed by: Peter Segal

Starring: Drew Barrymore, Adam Sandler

Awards: Won six awards

50 First Dates is an uncanny take on short term memory loss. No man would want to be in Henry Roth’s position (Adam Sandler) and it would obviously be very distressing to suffer like Lucy Whitmore (Drew Barrymore) without even knowing it. But the romantic comedy handles the subject and narrates a love story with élan.

This amusing and entertaining romantic comedy takes place on the Hawaiian island of Oahu, where a veterinarian meets a young girl and gradually falls in love with her. If you are an Adam Sandler fan and would like to have a few laughs during a movie, 50 First Dates is a great choice for you.

The favorite quote: There’s nothing like a first kiss.

10. WALL-E (2008)

IMDB Rating: 8.4/10

Directed by: Andrew Stanton

Starring: Ben Burtt, Elissa Knight, Jeff Garlin

Awards: Won one Oscar and 90 other awards

The captivating story set in the dystopian future, follows WALL-E, the robot who collects garbage, one piece at the time. Over the centuries, WALL-E has grown lonely, until one day he met EVE who was sent on a mission to prove that life on Earth is once again possible. Together, they go on an adventure that will change the destiny of the human race. You can find WALL-E on Amazon Prime, Netflix and the number of other streaming platforms.

The favorite quote: Dancing - A series of movements involving two partners, where speed and rhythm match harmoniously with music.

11. Eternal Sunshine of the Spotless Mind (2004)

IMDB Rating: 8.3/10

Directed by: Michel Gondry

Starring: Jim Carry, Kate Winslet

Awards: Won one Oscar and 72 more awards

This now iconic movie is the brainchild of the legendary Charlie Kaufman and Michel Gondry, the movie director that has made masterpieces like Be Kind Rewind or The Science of Sleep. Jim Carry and Kate Winslet delivered brilliant performances in one of the most heartfelt breakup stories ever created. This may not be the best movie to watch with your Valentine’s date if things haven’t been going well recently.

The favorite quote: Too many guys think I'm a concept, or I complete them, or I'm gonna make them alive. But I'm just a fucked-up girl who's lookin' for my own peace of mind; don't assign me yours.

12. Gone Girl (2014)

IMDB Rating: 8.1/10

Directed by: David Fincher

Starring: Rosamund Pike, Ben Affleck

Awards: Received an Oscar nomination and won 64 awards

This is by no means the most romantic movie you can watch on Valentine’s Day, but it is probably one of the most exciting ones. Any Dunne (Rosamund Pike) stages her own abduction with the aim of settling old scores with her husband. This story of betrayal and revenge shows how dangerous falling out of love can be.

The favorite quote: You two are the most fucked up people I’ve ever met, and I deal with fucked up people for a living.

13. La La Land (2016)

IMDB Rating: 8.0/10

Directed by: Damien Chazelle

Starring: Emma Stone, Ryan Gosling

Awards: Won 6 Oscars and 235 awards

In case you missed one of the best musicals of the decade, Valentine’s Day is the perfect time to watch it. This a story about an aspiring musician and a young actress who are trying to balance between their professional and personal lives. Beautiful cinematography, great acting and an amazing soundtrack only add to the list of reasons why you shouldn’t miss out on La La Land.

The favorite quote:  Here’s to the ones who dream, foolish as they may seem. Here’s to the hearts that ache. Here’s to the mess we make…

14. Her (2013)

IMDB Rating: 8.0/10

Directed by: Spike Jonze

Starring: Amy Adams, Scarlett Johansson, Joaquin Phoenix

Awards: 1 Oscar and 81 awards

Is romance possible in the age of artificial intelligence? Does technology alienate us from others and make it difficult for us to meet the right person? These are the questions this 2013 classic is trying to answer. Like all other Spike Jonze’s movies, Her is a true masterpiece that will keep your attention glued to the screen.

The favorite quote: Sometimes I think I've felt everything I'm ever gonna feel and from here on out I'm not going to feel anything new - just lesser versions of what I've already felt.

15. Edward Scissorhands (1990)

IMDB Rating: 7.9/10

Directed by: Tim Burton

Starring: Winona Ryder, Johnny Depp

Awards: Won 9 awards, received one Oscar nomination

Widely accepted as the movie that launched Johnny Depp to stardom, Edward Scissorhands is a compelling story about a man rejected by society who finds his place in the world through the power of love. Set in a phantasmagoric universe only Tim Burton could dream up, this heartwarming movie will draw you into its magical universe from the opening shot.

The favorite quote: Kim: Hold me.

Edward: I can’t

16. About Time (2013)

IMDB Rating: 7.8/10

Directed by: Richard Curtis

Starring: Rachel McAdams, Domhnall Gleeson

Awards: Won three awards

Time travel is one of the most exploited topics in the world of cinema since we have seen so many great movies that explore this subject. About Time may not be as iconic as Back to the Future, but its romantic take on changing the faith of the world through love is certainly heartwarming, as it reminds us that love is the most powerful force in the universe.

The favorite quote: She was then and still is to me the most beautiful thing in the world.

17. Flipped (2010)

IMDB Rating: 7.7

Directed by: Rob Renier

Starring: Madeline Caroll, Callan McAuliffe

Awards: Won just two awards

This period piece starts in the 1950’s and follows the lives of Bryce and Julianna, two second-graders throughout the years. This movie is going to make you laugh and cry as their love story unravels. This is a small movie, that doesn’t have any A-list superstars on its cast list, which makes it a special treat for cinephiles and couples in search of a movie they can watch on Valentine’s Day. 

The favorite quote: As we stood there I realized that all these years we never really talked. But that day we started.

18. 500 Days of Summer (2009)

IMDB Rating: 7.7/10

Directed by: Marc Webb

Starring: Zooey Deschanel, Joseph Gordon-Levitt

Awards: Won 17 awards

This 2009 indie movie has gained a cult status among the fans, as it utilizes a non-linear structure to tell a simple love story that takes place within 500 days. The movie jumps from day to day without a particular order as it tells the story of Tom and Summer’s relationship.

The favorite quote: Just because she likes the same bizarro crap you do doesn’t mean she’s your soulmate.

19. Love, Actually (2003)

IMDB Rating: 7.6/10

Directed by: Richard Curtis

Starring: Hugh Grant, Emma Thompson, Keira Knightly

Awards: Won 10 awards

The superb cast, brilliant British humor, and beautifully told stories of 8 different couples that are weaved together into a larger narrative make Love, Actually one of the best romantic comedies of the 21st century. Each storyline is different, and yet bound by the theme of love and set in London during the Christmas holidays.

The favorite quote: Tell her that you love her. You’ve got nothing to lose and you’ll always regret it if you don’t.

20. Juno (2007)

IMDB Rating: 7.4/10

Directed by: Jason Reitman

Starring: Ellen Page, Jennifer Garner

Awards: One Oscar and 89 awards

The fact that Juno won an Oscar for the Best Original Screenplay, is perhaps the best indicator of how powerful the story the movie tells really is. The topic of teen pregnancy and the difficulties that are associated with it may be a tad too much for a quiet evening with your Valentine’s Day date, but nonetheless, Juno is a must-see for anyone who appreciates the art of storytelling.

The favorite quote: In my opinion, the best thing you can do is find a person who loves you for exactly what you are. Good mood, bad mood, ugly, pretty, handsome, what have you, the right person will still think the sun shines out your ass. That's the kind of person that's worth sticking with.

21. Say Anything (1989)

IMDB Rating: 7.3/10

Directed by: Cameron Crowe

Starring: John Cusack, Ione Skye

Awards: No notable awards

If you are in a mood for a romantic teen comedy that follows the story of two young people who feel in love soon after graduating high school, then Say Anything… might be the right choice for you. Entertainment Weekly selected Say Anything… as the best modern movie romance, and featured the film on its 50 best high school movies list. Say Anything… is available on Hulu and Amazon Prime.

The favorite quote: I gave her my heart and she gave me a pen

22. The Lobster (2015)

IMDB Rating: 7.2/10

Directed by: Yorgos Lanthimos

Starring: Colin Farrell, Rachel Weisz

Awards: Won 33 awards

The surreal world Yorgos Lantimos created is surely not everyone’s cup of tea, but if you are a fan of art cinema, then you shouldn’t miss out on The Lobster. The movie is set in a not so distant future where single people are taken to The Hotel where they must find a new partner or face harsh punishment.

The favorite quote: A relationship cannot be built on a lie.

23. Definitely Maybe (2008)

IMDB Rating: 7.1/10

Directed by: Adam Brooks

Starring: Rachel Weisz, Ryan Reynolds

Awards: No notable awards

Breakups and divorces can be difficult to understand, especially to an 11-year old girl. Ryan Reynolds is a political consultant who is trying to keep the balance between his professional and private life while going through a divorce. Keeping his relationship with his daughter intact is yet another challenge he must face.

The favorite quote: Look, I know love isn’t a fairytale.

24. Ghost (1990)

IMDB Rating: 7.0/10

Directed by: Jerry Zucker

Starring: Whoopi Goldberg, Demi Moore, Patrick Swayze

Awards: Won 2 Oscars and 16 awards

Eternal love never ends, it continues even after death. After his girlfriend finds herself in danger Sam, played by Swayze seeks a way to keep her safe from harm. Whoopi Goldberg’s captivating performance in this movie earned her an Oscar and a Golden Globe award for the best actress in a supporting role.

The favorite quote: It’s amazing, Molly. The love inside, you take it with you.

25. Four Weddings and Funeral (1994)

IMDB Rating: 7.0/10

Directed by: Mike Newell

Starring: Andie MacDowell, Hugh Grant

Awards: Won 24 awards

Never say never, as even a sworn bachelor can discover true love. For Charles, it took for funerals to finally realize that he has found his soulmate. If you are a fan of British humor and looking for a slightly dark comedy you can watch on Valentine’s Day, this is probably one of the best choices you can make.

The favorite quote: Yes, it's odd, isn't it? All these years we've been single and proud of it and never noticed that two of us were, in effect, married all this time

26. One Day (2011)

IMDB Rating: 7.0/10

Directed by: Lone Scherfig

Starring: Anne Hathaway, Jim Sturgess

Awards: Won 2 awards

Based on the book written by David Nichols, One Day follows the stories of two college graduates who spent one night together after graduation. Throughout the years, life takes them to different places and prevents them from spending that day together each year. If you’re searching for a period piece that explores how the lives of two people develop despite the feelings they have for each other, then One Day may be the right movie for you.

The favorite quote: She made you decent and in return, you made her so happy.

27. Cinderella (2015)

IMDB Rating: 6.9/10

Directed by: Kenneth Branagh

Awards: Won 8 awards

This is a live-action adaptation of Disney’s 1950 classic animated film of the same name, based on the folk tale. The quest of recreating all the scenes from the original movie took years of preparation, but all this effort was worth the trouble as the final result is visually impressive.

The favorite quote: When there is kindness, there is goodness. When there is goodness, there is magic.

28. The Holliday (2006)

IMDB Rating: 6.9/10

Directed by: Nancy Meyers

Starring: Kate Winslet, Jude Law, Cameron Diaz

Awards: Won just two awards

Sometimes, all it takes to meet the right person is a simple change of scenery. Two old friends who struggle to meet the right guy decide to go to each other’s countries where they both manage to find true love. This is a light-hearted comedy that will surely put a smile on your face on Valentine’s Day. 

The favorite quote: I suppose I think about love more than anyone really should. I am constantly amazed by its sheer power to alter and define our lives.

29. Set It Up (2018)

IMDB Rating: 6.5/10

Directed by: Claire Scanlon

Starring: Zoey Deutch, Lucy Liu, Glen Powell

This Netflix production has a pretty simple but fun plot that will make your Valentine’s Day more enjoyable. Set It Up is far from being the most original romantic comedy ever made, but its plot that involves an elaborate scheme devised by two assistants to set up a date for their bosses is still pretty fun to watch.

The favorite quote: I like you. So, so much. You're not hard to get at all. You're hard to earn. It's so much better.

30. Valentine’s Day (2010)

IMDB Rating: 5.7/10

Directed by: Garry Marshall

Starring: Julia Roberts, Anne Hathaway, Jamie Foxx

Awards: Won 7 awards

If you don’t have a significant other, then watching a movie about the expectations and pressures of Valentine’s Day can be a great way to spend this Valentine’s Day. The star-studded cast delivers stunning performances across the different storylines the movie follows which makes it fun to watch.

The favorite quote: When you love someone, you love all of them. You gotta love everything about them, not just the good things but the bad things too. The things that you find lovable and the things you don't.

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Liza Brown
Liza Brown is a writer and a lover of all things video.