The best romantic comedies to watch on Valentine’s Day

Posted at 2:57 PM, Feb 14, 2016

(500) Days of Summer

If art imitates life, do the love stories we see on the big screen reflect reality? Throw in some comedy for effect, and you might come close to the sometimes messy, often poignant, but always heartfelt genre that is the romantic comedy.

Commonly referred to as rom-coms, these films make you laugh, cry and keep faith that your soulmate is out there somewhere. To identify the best rom-coms to enjoy on Valentine’s Day — or really any time of year — PrettyFamous looked for romantic comedies with over 50,000 IMDb votes. We then ranked the films by Smart Rating from high to low. Our Smart Rating (out of 100) is a weighted average of the following:

    • Rotten Tomatoes’ Audience Score
    • Data provider Gracenote’s Proprietary Rating, which is based on ratings from top critics at Variety, Newsday, Chicago Tribune, Rotten Tomatoes, and Metacritic.
    • Inflation-adjusted cumulative box office gross

Whether you’re watching a rom-com to celebrate Valentine’s Day or any time of year, this list has your must-sees.

Note: Ratings in the Smart Rating are all given equal weight, whereas box office gross has a lesser weight.

#30. My Big Fat Greek Wedding

Smart Rating: 83.70
Release Year: 2002

For Toula, marrying a non-Greek man won’t be as easy as it might seem, since she needs to contend with the overbearing — and often hilarious — protests of her very Greek family without driving him away in the process.

#29. Warm Bodies

Smart Rating: 84.00
Release Year: 2013

It’s about time they made a movie about a zombie who falls in love. When R (a member of the walking dead) meets a girl named Julie, he starts to remember what it’s like to be human, to feel and to love.

#28. About Time

Smart Rating: 84.17
Release Year: 2013

If you had the gift of time travel, would you change your past to alter the outcome of your future? A twentysomething named Time does just that when he traverses the space-time continuum to get the girl of his destiny.

#27. Antz

Smart Rating: 84.30
Release Year: 1998

Even ants need love. Z (voiced by the ever-neurotic Woody Allen) seeks to escape his oppressive colony, all the while trying to win over the heart of a princess (played by Sharon Stone), who in turn seeks to remove herself from an equally stifling kingdom.

#26. While You Were Sleeping

Smart Rating: 85.33
Release Year: 1995

When Lucy (played by Sandra Bullock) saves a man’s life, she pretends she’s engaged to him. She’ll need to do more than that, though, to convince the man’s brother (played by Bill Pullman) that her heart really belongs where she claims it does.

#25. Trainwreck

Smart Rating: 85.43
Release Year: 2015

In this newest installment from director Judd Apatow, the eponymous trainwreck of the film, Amy (played by Amy Schumer), must reconsider her hard-partying ways when she meets a nice, well-meaning guy (portrayed by Bill Hader).

#24. Bridget Jones’s Diary

Smart Rating: 85.53
Release Year: 2001

Bridget Jones, a single, lonely British woman, keeps a diary for one full year, chronicling her attempts to date, get in shape and avoid accidents. Based on the best-selling novel (which in turn was based on “Pride and Prejudice”), it put Renée Zellweger on the map.

#23. Crazy, Stupid, Love.

Smart Rating: 85.75
Release Year: 2011

Plenty of divorced men going through a midlife crisis have tried picking up girls at bars to compensate, but in “Crazy, Stupid, Love,” it proves hapless and memorable for Cal (Steve Carell), who might just get a second lease on love.

#22. Notting Hill

Smart Rating: 85.95
Release Year: 1999

Is it really possible for the Hollywood elite to make a relationship work with an average, non-famous person? Modest bookstore owner Will (Hugh Grant) finds out firsthand when he bumps into Los Angeles starlet Anna Scott (Julia Roberts) in London’s Notting Hill.

#21. Forgetting Sarah Marshall

Smart Rating: 86.07
Release Year: 2008

“Wrong place, wrong time” could never be more apropros in “Forgetting Sarah Marshall,” at least not for TV show producer Peter (Jason Segel), who, after jetting off to Hawaii to get over a breakup with his girlfriend Sarah (Kristen Bell), ends up running into her at the same resort. Only this time, she’s got her new boyfriend (Russell Brand) in tow.

#20. Pitch Perfect

Smart Rating: 86.42
Release Year: 2012

When college freshman Beca joins her school’s all-female a capella group, they’re tasked with competing against their male singing rivals, the Treblemakers, with one complication — the affections of one member named Jesse.

#19. Punch-Drunk Love

Smart Rating: 86.83
Release Year: 2002

How do phone-harrassing mattress salesmen, seven crazy sisters and copious amounts of pudding help down-and-out toilet plunger salesman Barry (Adam Sandler) meet the woman of his dreams? Watch “Punch-Drunk Love” and you’ll find out how it all makes sense.

#18. Scott Pilgrim vs. the World

Smart Rating: 87.07
Release Year: 2010

There are times when a guy needs to go to battle with his new girlfriend’s seven evil ex-boyfriends to secure her love. In this adaptation of the popular graphic novel series, that’s exactly what the title character (played by Michael Cera) must do with wit, music and cunning.

#17. Sleepless in Seattle

Smart Rating: 87.61
Release Year: 1993

When widower Sam (Tom Hanks) relocates to Seattle, he’s still grieving over the death of his wife, so his son calls into a radio talk show to express the loss his father feels. Intrigued and touched, it connects Sam with a reporter named Annie (played by Meg Ryan) in a way he never imagined.

#16. The 40-Year-Old Virgin

Smart Rating: 87.76
Release Year: 2005

Andy’s reached the age of 40 without ever having sex, and his nerdy, action-figure-collecting ways certainly hinder his chances of meeting the right woman. But a chance meeting with an attractive single mom and some good-hearted encouragement from his coworkers might just be what he needs to break the cycle of unintended celibacy.

#15. Chasing Amy

Smart Rating: 87.86
Release Year: 1997

Holden (Ben Affleck) and Banky are best friends until Holden’s interest in Alyssa — who happens to be a lesbian — threatens their friendship and ability to work together.

#14. Grosse Pointe Blank

Smart Rating: 87.88
Release Year: 1997

The name of the film is a reference to the town of Gross Pointe, where Martin (John Cusack) is attending his upcoming high school reunion. The Pointe Blank part? Martin grew up to become a hitman, and now his heart is burdened not just with the “job,” but rekindled feelings for his old girlfriend Debi (Minnie Driver). Like “High Fidelity,” Cusack proves he’s the king of the late ’90s indie rom-com.

#13. Enchanted

Smart Rating: 88.35
Release Year: 2007

There are fish-out-of-water stories, and then there are fish-out-of-water movies done Disney-style.

When a princess named Giselle (Amy Adams) gets on the bad side of a wicked queen, she’s exiled from her kingdom to modern-day Manhattan, where she ends up falling for none other than a divorce lawyer (Patrick Dempsey). Can he compete with a time-traveling prince sent to bring her back?

#12. (500) Days of Summer

Smart Rating: 88.80
Release Year: 2009

A love story that’s not a love story at all, “(500) Days of Summer” is told from the perspective of Tom (Joseph Gordon-Levitt), as he recalls his up-and-down relationship with manic pixie dream girl Summer (Zooey Deschanel). The only problem? The nonlinear narrative is meant to show us what Tom perceives as the highs and lows of his time dating Summer — and not, perhaps, how the relationship really unfolds.

#11. High Fidelity

Smart Rating: 90.19
Release Year: 2000

John Cusack portrays record store clerk Rob, who can’t seem to figure out why his relationships keep going sour — so his encyclopedic knowledge of music and all things “top five” give him pause to reflect on his last five breakups. Through a musical — and personal — journey, he discovers a bit more about himself, and learns a critical lesson drawing him back to someone he once lost.

#10. Jerry Maguire

Smart Rating: 90.75
Release Year: 1996

It’s not “Show me the money!” that makes people remember this mid-1990s Tom Cruise vehicle — It’s “You had me at hello.” When disgraced sports agent Jerry Maguire puts all his cards on one hot-shot football player, he also has to test his commitment to Dorothy (played by Renée Zellweger). Break out the Kleenex for the airport reunion scene.

#9. Four Weddings and a Funeral

Smart Rating: 91.38
Release Year: 1994

You might want to watch “Four Weddings and a Funeral” back to back with “Groundhog Day,” not only because they both feature ’90s rom-com queen Andie MacDowell, but for the keep-trying-until-you-find-love motif throughout both films.

The movie that put Hugh Grant on the map in the U.S., Grant plays Charles, who decides to dash his bachelor ways after crossing paths — and falling for — the same woman he meets at five separate social events.

#8. When Harry Met Sally…

Smart Rating: 92.41
Release Year: 1989

Can men and women just be friends without sex getting in the middle of it? It’s one of many relationship questions raised in Rob Reiner’s “When Harry Met Sally,” a story about Harry (Billy Crystal) and Sally (Meg Ryan), longtime platonic friends who flirt with romance over the course of 12 years. Connecting, losing touch, and reconnecting again, do Harry and Sally finally end up together in the end?

#7. Breakfast at Tiffany’s

Smart Rating: 92.56
Release Year: 1961

Blake Edwards’ adaptation of the famous Truman Capote romance does the novella justice as Audrey Hepburn‘s most recognizable, iconic and much-imitated character of Holly Golightly, a New York socialite whose affair with her new neighbor, Paul (played by George Peppard), doesn’t happen without some comedic complication — and a happy ending, at that.

#6. Shakespeare in Love

Smart Rating: 92.61
Release Year: 1998

Sometimes, it’s perfectly appropriate to take artistic liberty when rewriting the love lives of real people in history, which is why “Shakespeare in Love” stands the test of time as one of the greatest romance films.

While writing “Romeo and Juliet” (in itself a tragedy), William Shakespeare (portrayed by Joseph Fiennes) woos a wealthy businessman’s daughter (Gwyneth Paltrow), helping him overcome his writer’s block — but not without some cross-dressing hijinks and a stern judging from Elizabeth I herself.

#5. Midnight in Paris

Smart Rating: 92.75
Release Year: 2011

Surrealistic and starry eyed in a literal sense, Woody Allen’s 2011 comedy-fantasy follows Gil (Owen Wilson) as he travels back in time each night at midnight on the streets of Paris, meeting various famous artists, poets and musicians — think Salvador Dali, Vincent Van Gogh, Ernest Hemingway, and Pablo Picasso.

Through their wisdom and unique artistic perspective on life, Gil will never look at love the same way again.

#4. Groundhog Day

Smart Rating: 93.16
Release Year: 1993

Bill Murray‘s Phil Connors is lucky, in a sense. He gets the girl on Feb. 3, only after being cursed to repeat Groundhog Day over, and over, and over, and over again — all while kidnapping Punxsutawney Phil in the process.

If you’ve never received a second chance at love, this modern classic directed by the late, great Harold Ramis will show you how a third, fourth, fifth and sixth try can come with comedic consequences.

#3. Roman Holiday

Smart Rating: 94.52
Release Year: 1953

With the new biopic “Trumbo” up for accolades, it’s hard to deny the genius of Dalton Trumbo’s screenwriting in films like “Roman Holiday.” Directed by William Wyler, its plot has been copied but never bettered.

In their random encounter, opposites Ann (played by Audrey Hepburn) and Joe (portrayed by Gregory Peck), enter a whirlwind romance in Rome between princess and American journalist. The locale gives the film’s 1950s Italian locations a sweeping, picturesque beauty indicative of the era.

#2. The Artist

Smart Rating: 95.15
Release Year: 2011

Though it looks and plays out like a film from the Golden Age of Hollywood, “The Artist” is one of those newer period pieces that stays true to the integrity, honesty and realism of the era it portrays. This poignant film is a romance between a silent-film actor whose star is fading — and the young actress whose fame is rising.

#1. It Happened One Night

Smart Rating: 95.68
Release Year: 1934

Arguably the very first rom-com ever made, this Frank Capra-directed classic of the silver screen stars Clark Gable and Claudette Colbert (as a maverick newsman and spoiled socialite, respectively). The film shows how, despite some early misgivings, love has a chance. “It Happened One Night” went on to win five Oscars and define a whole genre.


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