The best romantic comedies to watch on Valentine’s Day

“It Happened One Night” happened 84 years ago, but it is still considered one of the best romantic comedies of all time. If you enjoy classic cinema, Clark Gable and Claudette Colbert, you’ll love watching this film about a spoiled socialite who runs away from home to elope with her love...only to end up falling for another man. “It Happened One Night” isn’t just funny and romantic, but it was also the first film to win all five major Academy Awards (Best Picture, Director, Actor, Actress and Screenplay).

How far would you go to stop a former flame from marrying the wrong man? Keeping her swamped at work? Having the man repeatedly and unlawfully arrested? Kidnapping his mother? Walter Burns (Cary Grant) does all of this while working alongside Hildy Johnson (Rosalind Russell), chasing scoop after scoop for The Morning Post in this classic comedy that owns a place in National Film Registry. Due to a copyright snafu, “His Girl Friday” entered the public domain in 1968, meaning you can legally watch it online free of charge!

No, we’re not talking about the story of how the Philadelphia Eagles came to defeat the New England Patriots in last year's Super Bowl (even though that's a fond memory for many of us), but instead a classic tale of the impending marriage of Tracy Lord (Katharine Hepburn) and how it is affected by the arrival of her ex-husband (Cary Grant) and a reporter (Jimmy Stewart) who hopes to cover the event. Although it came out 79 years ago, “The Philadelphia Story” is one of the rare films to hold a 100 percent rating on Rotten Tomatoes.

A wealthy man (Henry Fonda) falls for a con artist (Barbara Stanwyck), who finds herself unexpectedly falling for him in return. However, when she reveals her ruse, he rejects her, and she must reinvent herself as a different person, Eve, to win him back...or get her revenge. In case you somehow haven’t seen this 77-year-old classic, we won’t spoil it.

A certain wife would likely divorce a certain entertainment journalist if she saw that he made a list of the best romantic comedies and didn’t include “Roman Holiday.” After all, Gregory Peck and Audrey Hepburn make the perfect on-screen pair while gallivanting around one of the most romantic cities in the world. And given the fact that Peck plays a newsman who falls for a beautiful girl, it only makes sense that the aforementioned wife would enjoy this classic funny and lovey film.

Loosely based on the Truman Capote novel of the same name, “Breakfast at Tiffany’s” centers on Holly Golightly (Audrey Hepburn), a naive young socialite living in New York City who gets entangled in a will-they-won’t-they with Paul (George Peppard). Not only is this 1961 two-time Oscar-winning film often referred to as one of the best romantic comedies in Hollywood history (and is preserved in the National Film Registry as a result), but it also has since become Hepburn’s most iconic role.

Not everyone is a fan of musicals, but we couldn’t resist including at least one in this list. With a lot of silliness, many memorable songs and a cast led by Olivia Newton-John and John Travolta, “Grease” is a perfect fit for this list...especially if you enjoy throwbacks to the 1950s.

Tom Hanks, Daryl Hannah, John Candy and Eugene Levy headline the cast of Ron Howard’s 1984 rom-com “Splash.” As a 28-year-old newcomer with one film credit to his name, Hanks could have ruined his career with this silly mermaid fantasy flick. But it ended up receiving critical acclaim, earning Oscar and Golden Globe nods and even netting Hannah a Saturn Award for Best Actress. Today it holds a 92 percent rating on Rotten Tomatoes. According to Hollywood rumors, a remake is planned that will reportedly star Jillian Bell and Channing Tatum...with Tatum playing the mermaid (or merman)!

How many rom-coms in the last 50 years can boast about winning three Academy Awards? Only the one starring Cher and Nicolas Cage. “Moonstruck” nabbed Oscars for Best Actress (Cher), Best Supporting Actress (Olympia Dukakis) and Best Original Screenplay (John Patrick Shanley), not to mention Golden Globes for Best Actress and Best Supporting Actress.

“Mawwiage is what bwings us togeva today”...or at least it’s the theme of “The Princess Bride,” the 1987 romantic comedy fantasy film written by William Goldman and directed by Rob Reiner. Peter Falk, Cary Elwes, Robin Wright, Mandy Patinkin, Andre the Giant and Billy Crystal round out the all-star cast of this cult classic, which produced only a modest turnout at the box office but has since become a favorite of film fans both young and old.

Steve Martin didn’t just star in 1987’s “Roxanne,” he also wrote the screenplay, which was based on Edmond Rostand’s play “Cyrano de Bergerac.” The time between the play and the film? Ninety years. However, it was worth the wait, as Martin delivered as the large-schnozzed protagonist alongside Darryl Hannah. Unlike the play, “Roxanne” is much more of a feel-good story, making it perfect for the most romantic day of the year.

A perfect storm of director Rob Reiner, screenwriter Nora Ephron and actors Billy Crystal and Meg Ryan converged to form what some say is the greatest rom-com of all time. Dealing with the conundrum of whether or not men and women can truly be just friends, “When Harry Met Sally...” earned five Golden Globe nominations and an Oscar nod for Ephron and gave audiences one of the most memorable scenes to ever take place in a deli — the iconic Katz’s Deli in Manhattan, no less, which still posts a sign above the famous table hoping that you’ll “have what she had.”

Hugh Grant was the king of romantic comedies in the 1990s and early 2000s, and his first taste of international success was 1994’s “Four Weddings and a Funeral.” Not only did the film become the highest-grossing British film in cinema history at the time, but it also earned two Academy Award nominations — including Best Picture! Although “Four Weddings and a Funeral” couldn’t capitalize at the Oscars, Grant took home a Best Actor Golden Globe for his role as Charles, a “serial monogamist.”

Part rom-com, part coming-of-age film, 1995’s “Clueless” is a classic chick flick that doubles as a Beverly Hills fairy tale. Superficial teen Cher (Alicia Silverstone), along with her friend Dionne (Stacey Dash), pair two hapless teachers together before setting their sights on making over a new student named Tai (Brittany Murphy). However, Cher also has to come to terms with her own romantic feelings along the way...as if you really needed a summary of this iconic film. (Emphasis on “as if”!)

With any film from the Farrelly Brothers, you expect crudeness and immaturity. “There’s Something About Mary” definitely fits this description (with its outrageous and incredibly memorable scenes, most of which we can’t mention here). But the 1998 laugh riot is also sincere and filled with heart, which helped it surprisingly become the highest-grossing comedy in North America for that year while launching the careers of both Cameron Diaz and Ben Stiller. Not bad for the brothers’ second attempt at both writing and directing.

Remember what we said about Hugh Grant’s rom-com dominance? 1999’s “Notting Hill” is just another example. The film was written by Richard Curtis, who also penned the scripts for “Four Weddings and a Funeral,” “Love Actually” and “Bridget Jones’ Diary,” so Grant’s casting should come as no surprise. Oh, and Julia Roberts is in it too.

There have been countless highly acclaimed, foreign rom-coms throughout the years, but few have had the crossover appeal of 2001’s “Amélie.” Starring Audrey Tautou and directed by Jean-Pierre Jeunet, this French film focuses on a Parisian waitress who attempts to spread happiness to others while finding the same feeling within herself, in the form of a male suitor. “Amélie” was nominated for five Academy Awards and was a darling of the film festival circuit.

After reinventing herself, Bridget Jones (Renee Zellweger) gets wooed by both Daniel (Hugh Grant) and Mark ( Colin Firth), a situation that many people would die for... especially ladies in 2001 when this rom-com was released. Those looking for an updated take on “Pride and Prejudice” will enjoy this film, as will down-on-their-luck singles still hoping to find Mr. (or Mrs.) Right.

Let’s be real: How can a rom-com not succeed when it has a cast that includes Hugh Grant, Liam Neeson, Colin Firth, Laura Linney, Emma Thompson, Alan Rickman, Keira Knightley, Bill Nighy and Rowan Atkinson? (And that’s not even every famous face in the film!) Although it’s technically a Christmas movie, “Love Actually” is still totally appropriate for Valentine’s Day.

After our earlier jab at the New England Patriots, we'd like to extend an olive branch to our Boston-area friends by honoring a movie that honored the Red Sox's unlikely 2004 championship season. (After all, the Sox pulled off the feat again in 2018!) "Fever Pitch" is a remake of a 1997 film of the same name, which is in turn based on a 1992 book by Nick Hornby. However, the Farrelly Brothers changed the subject from soccer to baseball and cast the perfect duo of Jimmy Fallon and Drew Barrymore as co-leads. And for our readers who root for the Sox's most hated rival: Take comfort in knowing that Fallon, a New York native, is actually a diehard Yankees fan.

Whoever said all rom-coms need to be chick flicks? Written, directed and produced by comedic legend Judd Apatow, “The 40-Year-Old Virgin” is not your typical film about an unlucky virgin. It’s a raunchy, cringe-worthy and all-too-accurate summary of sex and dating in the 21st century. Helmed by Steve Carell in his first starring role, “The 40-Year-Old Virgin” actually received two thumbs up by Ebert & Roeper, with the former saying he was “surprised by how funny, how sweet and how wise the movie really is.”

Fall in love, get married, have kids. That’s the order of how life is supposed to go, many people claim. However, that’s not always how it unfolds...and it doesn’t have to! “Knocked Up” is the story of two people (Katherine Heigl and Seth Rogen) who unexpectedly become linked to each other and how they and their friends and family (including Leslie Mann, Paul Rudd, Jonah Hill and the late Harold Ramis) figure out what the future has in store. Super quotable and full of heart, “Knocked Up” is a modern-day romance story packed with laughs from the first scene to the last.

Plenty of rom-coms focus on finding love, but few address the next step. In 2009’s criminally underrated “Away We Go,” the comedic and believable married couple of John Krasinski and Maya Rudolph suddenly find out they are expecting a child and set off on a cross-country quest to figure out how and where to raise their future family. Thanks to a tight script and the likes of Allison Janney, Jeff Daniels, Catherine O’Hara and Jim Gaffigan in supporting roles (among others), “Away We Go” is a heartstring-pulling romantic dramedy that ultimately becomes a feel-good experience.

As if a failed bakery and lack of serious relationships isn’t bad enough for Annie Walker (Kristen Wiig), her best friend (Maya Rudolph) just got engaged. Now Annie must deal with not only losing her friend to a marriage but also possibly to another bridesmaid...while simultaneously being courted by an Irish-American police officer (Chris O’Dowd). Although friendship is the predominant theme in this wildly funny and oftentimes inappropriate film, love is a close second.

Nowadays, it’s not often that a rom-com (or rom-com-drama) finds its way into the major award shows, making “Silver Linings Playbook” an enticing option this Valentine’s Day, as it comes with eight Oscar and four Golden Globe nods, with one win for each. It stars the talented and easy-on-the-eyes duo of Bradley Cooper and Jennifer Lawrence, has screen icon Robert De Niro in a supporting role and was written and directed by David O. Russell (who adapted it from a book of the same name by Matthew Quick).

The most recent film on this list combines two huge stressors in a relationship: a partner falling seriously ill and dealing with a partner’s family. When the two occur concurrently, chaos ensues. However, this story — written by comedians Kumail Nanjiani and Emily V. Gordon and based on their actual relationship — is full of heart and plenty of laughs. “The Big Sick” owns a 98 percent rating on Rotten Tomatoes and won Best Romance Movie 2017 at the Golden Tomato Awards, and Nanjiani and Gordon were nominated for a Best Screenwriting Academy Award.