Special Report

Best Movies To Watch on Valentine’s Day

Courtesy of Miramax

Valentine’s Day is named for a saint who was martyred in 296. He was known for, among other things, a purple amethyst ring he wore regularly. The stone was considered a symbol of love throughout a portion of the period of the Roman Empire. A poem by Chaucer written in the 14th Century, linked Valentine directly to romantic love.

Valentine’s Day began to be a regularly celebrated holiday in the U.K. around 1800, and in the United States became part of the same tradition of the celebration of romantic love at about the same time. 

Valentine’s Day has become a big business for retailers. It is estimated that a typical American spends over $140 on Valentine’s Day gifts.

There are several movies about Valentines Day itself. The most well known of these carries the name of the holiday. “Valentine’s Day” was released in 2010, and starred Julia Roberts, Jamie Foxx, Anne Hathaway, and Jessica Alba. Its box office draw totalled a reasonable $110 million.

24/7 Tempo examined romantic movies that make for particularly good viewing on Valentine’s Day. We looked at several databases, in particular IMDB. We picked 20 movies, widely known, and fairly successful financially as the best movies to watch this Valentine’s Day.

Many of the films on this list were critically well received, managed to capture the top spot at the box office,and were out in theaters on Feb 14. These are the most popular movies for Valentine’s Day since 1980.

Click here to see the best movies to watch on Valentine’s Day

Courtesy of New Line Cinema

20. Valentine’s Day (2010)
> Genre: Romance, Comedy
> Starring: Julia Roberts, Jamie Foxx, Anne Hathaway, Jessica Alba

Each of the characters in the film live in Los Angeles. The movie chronicles how an individual Valentine’s Day turns out for each. In one case, the experience is a first date. In another, one of the characters reunite with a former love. While the film has been characterized as a mishmash of people doing different things, at different times, in different places, its star power helps carry the movie.

[in-text-ad]

Courtesy of Warner Bros.

19. The Phantom of the Opera (2004)
> Genre: Romance, musical, drama
> Starring: Gerard Butler, Emmy Rossum, Patrick Wilson

One would think a movie about a disfigured man who haunts an opera house would be far too depressing to be considered a romantic vehicle, However, the film which is based on the 1986 musical The Phantom of the Opera by Andrew Lloyd Webber is considered among the most haunting romances of the cinema. The relationship between the singer and dancer Christine Daaé and the Phantom is also considered among the most well known in serious romantic musicals. Spoiler alert: Things don’t turn out well for the Phantom.

Courtesy of Paramount Pictures

18. Titanic (1997)
> Genre: Romance, tragedy, drama
> Starring: Leonardo DiCaprio, Kate Winslet

The tale of the doomed luxury lines is among the most well known tragedies in American history. In the film, Leonardo DiCaprio, a poor young man, travelling in steerage, falls in love with first class passenger Kate Winslet. Both Winslet’s boyfriend and family make the romance impossible. However, they are united in bonds of love as the Titanic sinks. One of them does not make it to the final frame alive.

Courtesy of Buena Vista Pictures

17. Beauty and the Beast (1991)
> Genre: Romance, animated
> Starring: Paige O’Hara, Robby Benson

This film was made twice. This, the animated version, usually is the better regarded. The 2017 version which starred Emma Watson and Dan Stevens has often been criticized as wooden. It has also been made into a stage production. The plot is simple. A prince has been cursed to live his life in the form of an ugly animal. He is, however, a prince, which offers some attraction to a potential romantic interest. He takes the “beauty” prisoner, but she loves him nevertheless. They live happily ever after.

[in-text-ad-2]

Courtesy of Miramax

16. Bridget Jones’s Diary (2001)
> Genre: Romance, comedy
> Starring: Renée Zellweger, Colin Firth, Hugh Grant

The slightly less than attractive character played by Zellweger, spends the better part of the year keeping a diary about what she hopes will happen in her love life, but has not. Fairly suddenly, she has two interested male companions in Firth and Grant. Not to spoil the ending, things turn out better for one suitor than for the other. The films did well enough to trigger Bridget Jones: The Edge of Reason (2004), and Bridget Jones’s Baby (2016).

Courtesy of Warner Bros.

15. The Lake House (2006)
> Genre: Romance, drama
> Starring: Keanu Reeves, Sandra Bullock, Christopher Plummer

From a plot standpoint, this film belongs at the odd movie end of the spectrum. Two people, Bullock and Reeves share the same house at the same time, in different years. That, clearly, does not make sense. They also share love letters, although through most of the movie, they do not meet one another. Anything more said here would ruin the ending.

[in-text-ad]

Courtesy of Warner Bros.

14. City of Angels (1998)
> Genre: Romance, drama
> Starring: Nicolas Cage, Meg Ryan

One of the few good movies Cage ever made, and one of the few serious films in Ryan’s portfolio. Cage, an angel sent watch over humans, falls in love with one of them–Ryan, who plays a compassionate doctor. The only way Cage can have a romantic relationship is to give up his position in heaven. His decision does not turn out well for either of them.

Courtesy of Universal Pictures

13. Love Actually (2003)
> Genre: Romance, comedy
> Starring: Hugh Grant, Martine McCutcheon, Liam Neeson, Laura Linney

One of the appeals to audiences is likely the star power of the movie, which would be hard to match. It’s Christmas, in and around London. Eight couples. Eight romances. Some heartache. Some betrayal. Grant steals the show in his role as the Prime Minister of England.

Courtesy of Miramax

12. Kate & Leopold (2001)
> Genre: Romance, comedy, fantasy
> Starring: Meg Ryan, Hugh Jackman, Liev Schreiber

Something many romance films share is nonsensical plots. Jackman is a prince. He is mysteriously and inadvertently dragged from 1876 into present day New York. Ryan is an advertising executive who falls for him. No surprise. Jackman has been a romantic lead in movies for decades, and has not aged during the process. By the end of the film, they both end up in one of the two time periods, together. It would spoil the plot to say which one.

[in-text-ad-2]

Courtesy of Columbia Pictures

11. The Wedding Planner (2001)
> Genre: Romance, comedy
> Starring: Jennifer Lopez, Matthew McConaughey

In one of her least endearing roles, superstar movie actress and singer Lopez is a wedding planner. Among the rules of the trade is falling in love is taboo. McConaughey should be off limits. However, it does not work out that way. This is among the few romances in which almost everyone gets what he or she wants, in the end.

Courtesy of Buena Vista Pictures

10. Sweet Home Alabama (2002)
> Genre: Romance, comedy
> Starring: Reese Witherspoon, Patrick Dempsey

Straight of her massive success in Legally Blonde (2001), Witherspoon stars as a socialite down from the big city back to her original hometown in Alabama to divorce her husband–whom she has not seen in seven years. But, the spark has not died, she finds out over the better part of two hours.

[in-text-ad]

Courtesy of Warner Bros. Pictures

9. Casablanca (1942)
> Genre: Romance, drama
> Starring: Humphrey Bogart, Ingrid Bergman, Paul Henreid

Widely considered one of the greatest films of all time, Bogart and Bergman, past lovers, find themselves together in the midst of Nazi controlled French Morocco. Since they last saw one another Bergman has married a resistance hero. Bogart faces one of the great moral dilemmas in American film history. Viewers have been left, for decades, to decide if he made the correct decision.

Courtesy of Metro-Goldwyn-Mayer

8. Gone with the Wind (1939)
> Genre: Romance, drama
> Starring: Clark Gable, Vivien Leigh, Leslie Howard, Olivia de Havilland

On an inflation adjusted basis, the film has the highest box office sales of all time. Due to a racist view of Black Americans, it has lost almost all of what was a considerable luster. Scarlett O’Hara, played by Leigh, and Rhett Butler, played by Gable, hold the romantic center of this widely lavish story of the Civil War South. Until recently, it was often found on lists of the best movies ever made.

Courtesy of United Artists

7. The African Queen (1951)
> Genre: Romance, drama
> Starring: Humphrey Bogart, Katharine Hepburn

Bogart and Hepburn were each past their primes. Nevertheless, they joined director John Houston in Uganda and the Congo in Africa to make this film about an unlikely spinster’s romance with a steamer mechanic. The movie was written by doomed film critic, poet, and novelist James Agee. Using just their tiny steamer, Bogart and Hepburn join to sink a German warship. Both live.

[in-text-ad-2]

Courtesy of Metro-Goldwyn-Mayer

6. The Philadelphia Story (1940)
> Genre: Romance, drama
> Starring: Cary Grant, Katharine Hepburn, James Stewart

This film was made twice. The first, with this title, and then again as High Society (1956), starring Bing Crosby, Grace Kelly, and Frank Sinatra. Both are widely regarded. A socialite is about to embark on her second marriage. Two guests arrive for the festivities. One is her ex-husband. Another is a handsome society photographer. Two of the three get married. It would spoil the movie to say who.

Courtesy of Columbia Pictures

5. From Here to Eternity (1953)
> Genre: Romance, drama
> Starring: Burt Lancaster, Montgomery Clift, Deborah Kerr, Donna Reed, Frank Sinatra

This may be the most star-heavy movie on the list. And, the story is tragic enough that some people may consider it anti-romantic. An officer’s wife Kerr, falls for a sergeant, Lancaster. In the Army, that is bad karma. The movie resuscitated the career of Frank Sinatra. The famous “kissing in the surf” scene is worth the price of admission. The movies does not end well for any of the major characters

[in-text-ad]

Courtesy of 20th Century Fox

5. The Sound of Music (1965)
> Genre: Romance, drama, musical
> Starring: Julie Andrews, Christopher Plummer

The public was reminded of how much Plummer, who died last week, despised this film. He plays a retired naval officer who has moved, with his seven children, to the mountain section of Austria. Andrews is sent to be their governess. Despite her attempt to tear down the discipline he has built to control his children, they fall for one another. The movie made Andrews a mega-star.

Courtesy of Warner Bros.

4. Giant (1956)
> Genre: Romance, Western
> Starring: Elizabeth Taylor, Rock Hudson, James Dean

Hudson, who owns one of the largest ranches in Texas, goes to Maryland to buy a prize horse. He returns to Texas with a new wife as well. Taylor is at her most radiant. The film follows them across a period of 40 years, as ranchers, oilmen, and, eventually, among the wealthiest families in America. Known for its depiction of racism against Mexican Americans, and its place as the last role in young James Dean’s life.

Courtesy of Warner Bros.

3. My Fair Lady (1964)
> Genre: Romance, Western
> Starring: Audrey Hepburn, Rex Harrison, Stanley Holloway

Based on the Broadway musical which in turn was based on George Bernard Shaw’s play Pygmalion (1913). Hepburn is a poor young girl who speaks with a Cockney accent. A professor, played by Harrison, wagers with one of his friends that he can train her well enough in British upper class social skills so that she can pass as someone who was born and bred to the manor. Hepburns feelings get hurt, temporarily.

[in-text-ad-2]

Courtesy of Warner Bros.

2. The Bodyguard (1992)
> Genre: Romance, drama, thriller
> Starring: Kevin Costner, Whitney Houston

Houston plays what she was in real life–a megastar singer. Costner, a former Secret Service agent, is hired to protect her after she receives several threats. Someone makes good on at least one of these, and Costner and Houston find themselves trapped together in dark, wintery woods–with their families. Danger is all around them. They fall in love.

Courtesy of Paramount Pictures

1. Love Story (1970)
> Genre: Romance, drama, tragedy
> Starring: Ali MacGraw, Ryan O’Neal

The film does not turn out well, but on the way to its conclusion it is touchingly romantic. As is true among many of the best romances, this is set at Harvard Law School. O’Neal is from a rich, WASP, east coast family, who would like to see their son marry well. MacGraw comes from a lower middle class background. “Love — Love means never having to say you’re sorry”

100 Million Americans Are Missing This Crucial Retirement Tool

The thought of burdening your family with a financial disaster is most Americans’ nightmare. However, recent studies show that over 100 million Americans still don’t have proper life insurance in the event they pass away.

Life insurance can bring peace of mind – ensuring your loved ones are safeguarded against unforeseen expenses and debts. With premiums often lower than expected and a variety of plans tailored to different life stages and health conditions, securing a policy is more accessible than ever.

A quick, no-obligation quote can provide valuable insight into what’s available and what might best suit your family’s needs. Life insurance is a simple step you can take today to help secure peace of mind for your loved ones tomorrow.

Click here to learn how to get a quote in just a few minutes.

Thank you for reading! Have some feedback for us?
Contact the 24/7 Wall St. editorial team.