5 Greatest Romantic Movies You Should Watch This Valentine’s Week – Ranked

This Valentine's week, you and your significant other should sit back, relax, and watch some of the greatest romantic movies ever.

5 Greatest Romantic Movies You Should Watch This Valentine's Week - Ranked

SUMMARY

  • It's the most romantic day of the year, Valentine's Day, on Wednesday February 14th this year.
  • You and your significant other - or just you, if you're a single person - should sit back, relax, and watch some of the most romantic movies ever made on the big day.
  • The films you should consider watching include 2004's The Notebook and 1942's Casablanca.
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Valentine’s Day is fast approaching – the most romantic day of the year – and couples worldwide will look for things to do to make the day special. A night in a luxury hotel, a delicious meal, a romantic walk, or exchanging meaningful gifts may be on the agenda. For others, an evening on the sofa watching romantic movies might suffice.

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If that’s what you and your significant other plan on doing – or if you’re a single person who wants to join in the Valentine’s fun – these five romantic films are great options to set the mood.

5. The Notebook (2004)

Rachel McAdams and Ryan Gosling in The Notebook
Rachel McAdams and Ryan Gosling in The Notebook.

When people think of iconic modern romantic movies, one of the first that springs to mind is Nick Cassavetes’ romantic drama The Notebook. Based on Nicholas Sparks’ 1996 novel of the same name, it tells the story of Noah and Allison “Allie” Calhoun, a couple in the 1940s. Their story is read by an elderly man from a notebook to his fellow nursing home resident in the present day. The elderly man is revealed to be Noah, and his fellow resident is Allie, who is suffering from dementia.

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It stars Ryan Gosling and Rachel McAdams as the young Noah and Allie, with James Garner and Gena Rowlands playing the older versions. The supporting cast includes James Marsden, Kevin Connolly, and Sam Shepard. It’s a visually striking, incredibly touching, and sentimental movie. Anyone looking for a Valentine’s Day tear-jerker should watch The Notebook.

4. Brokeback Mountain (2005)

Jake Gyllenhaal and Heath Ledger in Brokeback Mountain
Jake Gyllenhaal and Heath Ledger in Brokeback Mountain.

Adapted from Annie Proulx’s 1997 short story of the same name, Ang Lee’s neo-Western romantic drama Brokeback Mountain tells the story of the friendship and subsequent homosexual romantic relationship between two cowboys in the American West, which becomes complicated when they both marry their respective girlfriends in the period spanning from 1963 to 1983.

It stars the late Heath Ledger and Jake Gyllenhaal as Ennis Del Mar and Jack Twist, the two cowboys, with Linda Cardellini, Anna Faris, Anne Hathaway, and Michelle Williams in supporting roles. Brokeback Mountain is a beautiful, heartbreaking movie with exceptional Oscar-nominated performances from its leads.

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3. When Harry Met Sally… (1989)

Meg Ryan and Billy Crystal in When Harry Met Sally...
Meg Ryan and Billy Crystal in When Harry Met Sally…

The romantic comedy-drama When Harry Met Sally…, directed by Rob Reiner, is one of cinema’s most memorable rom-coms. It chronicles a dozen years of chance encounters between the eponymous characters from the moment they meet after graduating from the University of Chicago and sharing a drive to New York City.

It stars Billy Crystal and Meg Ryan as the eponymous Harry Burns and Sally Albright. Carrie Fisher, Bruno Kirby, and Steven Ford provide excellent support. It’s charming, funny, touching, superbly performed and directed, and buoyed by its iconic leads’ fantastic and almost palpable chemistry.

2. The Princess Bride (1987)

Robin Wright and Cary Elwes in The Princess Bride
Robin Wright and Cary Elwes in The Princess Bride.

Based on William Goldman’s 1973 novel of the same name, The Princess Bride – another movie directed by Rob Reiner – is a fantasy adventure with elements of romance and comedy. Told via a metafictional narrative style, it’s about a farmhand and skilled swordsman named Westley who, along with the friends he makes along the way, embarks on a quest to rescue his lover, Princess Buttercup, from a nefarious Prince.

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It stars Cary Elwes and Robin Wright as Westley and Princess Buttercup, with support from a fantastic ensemble that includes Mandy Patinkin, Chris Sarandon, Christopher Guest, Wallace Shawn, André the Giant, Peter Falk, and Fred Savage. This clever, exciting film is among the most joyous ever. Its romantic damsel-in-distress aspect makes it perfect for a Valentine’s Day adventure.

1. Casablanca (1942)

Humphrey Bogart and Ingrid Bergman in Casablanca
Humphrey Bogart and Ingrid Bergman in Casablanca.

Casablanca is one of the finest movies in cinema history. The legendary romantic drama, set during World War II, follows an American expat forced to choose between the woman he loves and helping her Czech resistance leader husband escape from the Vichy-controlled eponymous Moroccan city to keep fighting the Nazis.

It stars Humphrey Bogart as expat Rick Blaine and Ingrid Bergman as Ilsa Lund, the woman he loves. Paul Henreid, Claude Rains, Conrad Veidt, and Sydney Greenstreet provide expert support. Casablanca is tremendous and won the Outstanding Motion Picture Oscar. It’s a must-see film that’s engrossing, superbly acted, suspenseful, and, most importantly, hopelessly romantic.

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Written by Kevin Stewart

Articles Published: 77

Kevin Stewart is a full-time professional freelance writer and editor with 10 years of experience in the industry. He's produced more than 2000 pieces of published work on sports and entertainment topics - work that includes listicles, news articles, feature articles, voice-over scripts, quizzes, opinion pieces, and more. He's worked for the likes of NBC SYFY, Paste Magazine, FourFourTwo, Screen Rant, Digital Spy, CBR, WhatCulture, College Humor, The Richest, SportsKeeda, The Sportsman, and SugarScape. As an editor, he's managed the work of teams of up to 45 writers. He's a former business owner who's educated to degree level and has a BA Hons in Business Management. He loves movies (especially horror, 80s films, and superhero flicks), football (Tottenham Hotspur fan), keeping fit, and travelling the world.