The 58 Best Romantic Movies to Watch This Valentine's Day
Delight over exciting romance movies or have a cozy night in with your favorite rom-coms this Valentine’s Day. The 58 Best Romantic Movies to Watch This Valentine's Day is the perfect way to cuddle up and watch a movie about love this year PLUS 8 BONUS Romantic Movies to watch as well. Whatever your Valentine’s Day mood, there is a rom-com movie for everyone.
Romantic comedies are all about the kind of love that turns everything upside down. With so many different romance movies out there today, it can be difficult to select the best rom-coms from just more of the same Valentine's Day movies. I like to think I can spot a good film to watch on Valentine’s Day since I’ve been watching them for so long! Since there are so many excellent romantic comedies, it is hard to choose from the numerous comprehensive all-inclusive lists!
I have done all the hard work for you and compiled a list of the Fifty Best Romantic Movies to Watch on Valentine’s Day. I have separated these Top 50 Rom-Coms into separate lists: The 27 Best Classic Romantic Movies, The 9 Best 80’s Romantic Movies to Watch, The 9 Best 90’s Romantic Movies to Watch, and The 13 Best Modern Day Romantic Movies to Watch This Valentine's Day for a total of The 58 Best Romantic Movies to Watch This Valentine's Day.
The 27 Best Classic Romantic Movies to Watch This Valentine's Day
Nothing says romance more clearly, or I should say no one, other than Clark Gable. This man oozes romance! It Happened One Night is — HANDS DOWN — the very best Rom-Com EVER MADE!! Also included in this list of the 27 Best Classic Romantic Movies, of course, include other movies Clark Gable made. This list also MUST include the duo of Katherine Hepburn and Spencer Tracey. I pretty much LOVE and adore any movie with the two of them in it. Naturally, Cary Grant HAS to be in all the classic Rom-Coms, as well as the ever-gorgeous Audrey Hepburn! Introduced later in the Classic Romance list is Marilyn Monroe - she has to be included as well - because, girl is funny and sexy!
One of my all-time favorite movies is on this list too — Pillow Talk with Doris Day! Adore her! I can say in all honesty, I think I have seen this movie at least 1,000 times! Another movie that is one of my favorites — Guess Who’s Coming to Dinner — one of the first interracial movies ever made about love! Still SO GOOD today! Also included is the every sexy Humphrey Bogart. James Stewart, the funny guy himself makes the list and so does Ingrid Bergman.
IT HAPPENED ONE NIGHT (1934) STREAM NOW ON AMAZON
And down come the walls of Jericho! Arguably the Rosetta stone of rom-coms, Frank Capra’s Oscar-winning behemoth pairs one hoity-toity heiress (Claudette Colbert) and one desperate investigative journalist (Clark Gable, singlehandedly killing the undershirt business) on one long, crazy road trip. The fact that this farce skirted in right under the wire before the Hays Code started getting rigid on risque material lends an extra layer of erotic friction to the laughs — not to mention the fact that the two leads were at their sexiest and their funniest in 1934. (All apologies, The Palm Beach Story.) Everyone remembers the hitchhiking scene, but personally, we stan for the sequence in which Gable carries Colbert across a river over his shoulder. Still hilarious, still hot.
THE AWFUL TRUTH (1937) STREAM NOW ON AMAZON
Jerry (Cary Grant) and Lucy (Irene Dunne) are a married couple who doubt each other's fidelity: Jerry suspects Lucy and her music teacher (Alexander D'Arcy) of spending an evening together, and Lucy is convinced Jerry lied about a business trip. When the jealous pair file for divorce, both rush into new relationships, but quickly realize their love never died. The soon-to-be-divorced husband and wife then both scramble to spoil each other's chances for newfound romance
HOLIDAY (1938) STREAM NOW ON AMAZON
Johnny (Cary Grant) seems like a solid match for Julia (Doris Nolan), the socialite daughter of Edward Seton (Henry Kolker). Assured that Johnny is a worthy suitor, Edward approves of the pairing. But, as Johnny's wanderlust surfaces -- he is more interested in traveling than in business -- Edward starts to have doubts. Johnny also begins to wonder if he might not be a better match for Linda (Katharine Hepburn), Julia's outspoken younger sister, with whom he has much more in common.
BRINGING UP BABY (1938) STREAM ON AMAZON
Howard Hawks’ genuinely uproarious, innuendo-filled romp was a bomb upon release — a piece of trivia that only adds to the merits of this screwball masterpiece. Cary Grant’s bumbling Dr. David Huxley just wants one last bone [ahem] to build his brontosaurus. Instead, he’s pushed to the brink of sanity at breakneck speed by Katharine Hepburn’s irrepressible, scatterbrained heiress Susan Vance, who hopes to save him from a marriage that promises to be dustier than a dinosaur fossil. A simmering frustration leads, naturally, to love — but not before they spend half their time together chasing animals, from an impish terrier to a leopard named Baby (the film long predated our current mania for furry thespians).Woman of the Year' (1942)
When Tracy Met Hepburn: From the moment his sportswriter and her political columnist lock eyes on each other in their editor’s office, you can practically feel the electric charge being exchanged between these two actors. George Stevens’ battle-of-the-sexes showdown was the first of nine movies that Spencer Tracy and Katharine Hepburn would make together, and it immediately established the template for their comedies: He was a salt-of-the-earth rascal; she was a sometimes snobbish, always sophisticated lady; together, they were a near-perfect screen couple. No offense to Adam’s Rib or Pat and Mike, but this initial pairing is still the best example of why they’re a legendary rom-com duo. Not even that seriously retrograde ending can ruin it.
THE SHOP AROUND THE CORNER (1940) STREAM NOW ON AMAZON
Alfred Kralik (James Stewart) and Klara Novak (Margaret Sullavan) are employees at Matuschek and Company, a general store in Budapest. Klara and Alfred are constantly at odds with each other, butting heads and disagreeing on almost everything. Both are enamored of their respective pen pals, who serve as welcome distractions in their lives. Little do they know, they are each the other's pen pal and, despite outward differences, have unwittingly fallen in love through their letters.
THE PHILADELPHIA STORY (1940) STREAM NOW ON AMAZON, HBOMAX
“Either I’m gonna sock you or you’re gonna sock me!” “Shall we toss a coin?!” The Philadelphia Story’s verbal pyrotechnics are merely part of the brilliance of this 1940 Oscar-winner, in which dejected ex-husband C.K. Dexter Haven (Cary Grant) conspires with journalist Mike Connor (Jimmy Stewart) to crash the glitzy wedding of Haven’s former wife Tracy Samantha Lord (Katharine Hepburn). Fans love the biting back-and-forth dialogue among this trio of combatants — a scenario that only gets more complicated once she starts falling for both men. But beyond the witty repartee and impossibly beautiful actors, director George Cukor skillfully underlines the poignancy of people using love as a quick fix for deeper insecurities and gnawing dissatisfactions. All that, plus a pitch-perfect urbane tone, airtight plotting and the best flirty effervescence the Golden Age of Hollywood could buy. Pure rom-com bliss.
HIS GIRL FRIDAY (1940) STREAM ON AMAZON
In this corner: Cary Grant, the world’s most dashing newspaper editor. In that corner: Rosalind Russell, his ace reporter, who also happens to be his ex-wife. In a few days, she’s getting married to bland ol’ Ralph Bellamy (right!) and leaving the news racket forever — but first, these two have one last big story to break. Howard Hawks adapted the play The Front Page, turning the reporter into a woman, with Russell yelling endearments like “Now get this, you double-crossing chimpanzee!” It remains one of the speediest comedies ever made — Hawks wrote overlapping dialogue to better mimic the way people talk, then asked his actors to read the lines twice as fast as usual. In the days before Robert Altman or Veep, no movie crammed in so many rapid-fire insults per minute.
THE LADY EVE (1941) STREAM ON AMAZON
No old-school Hollywood couple can match the acid-to-alkaline chemistry of Barbara Stanwyck and Henry Fonda. She’s a con artist aboard a cruise ship who sets her sights on the big game: Fonda, a mild-mannered reptile scholar and heir to the Pike Ale fortune. (“The ale that won for Yale!”) The gold diggers are after him — as Stanwyck sneers, “Every Jane in the room is giving him the thermometer” — but no woman can turn his head from his books and his pet snake… until Stanwyck steps in to destroy his life. Preston Sturges crams this classic with nonstop barbs (“Why Hopsie — you oughta be kept in a cage!”) in a screenplay where every line is endlessly quotable, right down to the final four words. Positively the same dame!
WOMAN OF THE YEAR (1942) STREAM ON AMAZON
Tess Harding (Katharine Hepburn) is a progressively-minded political journalist. Sam Craig (Spencer Tracy) is a sports writer with very traditional values. The only thing the two have in common is that they both work for the same New York City newspaper. Despite an initial and mutual dislike, the two eventually fall in love and get married. When Tess wins the Woman of the Year award, traditional gender roles become flipped and their relationship suffers as a result.
THE MORE THE MERRIER (1943) STREAM ON AMAZON
A scandalous romantic comedy about roomers and rumors. Arriving in Washington to help with the war effort, Benjamin Dingle (Charles Coburn), a retired, well-to-do millionaire, needs a place to stay. So when patriotic Connie Milligan (Jean Arthur) decides to rent out half her apartment, Mr. Dingle promptly moves in. Firmly believing that everybody's business is everybody's business, Mr. Dingle quickly determines that Connie should be married to a clean-cut nice young man. So he rents out half of his half to Joe Carter (Joel McCrea), an Army sergeant who most certainly fills the bill. But when the newspapers get wind of their "scandalous" living arrangement, it's up to Mr. Dingle to save careers, reputations, and a budding romance, in this delightful screwball comedy.
ADAM'S RIB (1949) STREAM ON AMAZON
A courtroom rivalry finds its way into the household when prosecuting lawyer Adam Bonner (Spencer Tracy) faces off against his wife, Amanda (Katharine Hepburn), who happens to be a defense attorney. Working on opposite sides of a lawsuit where a woman (Judy Holliday) has shot her cheating husband (Tom Ewell), Adam and Amanda are both determined to win the case, and their home becomes the setting for comical showdowns, with neither spouse willing to relent.
THE IMPORTANCE OF BEING EARNEST (1952) AMAZON STREAM
Oscar Wilde's comic jewel sparkles in Anthony Asquith's film adaptation of THE IMPORTANCE OF BEING EARNEST. Featuring brilliantly polished performances by Michael Redgrave, Joan Greenwood, and Dame Edith Evans, the enduringly hilarious story of two young women who think themselves engaged to the same nonexistent man is given the grand Technicolor treatment. Seldom has a classic stage comedy been so engagingly transferred to the screen.
PAT AND MIKE (1952) STREAM ON AMAZON
Pat Pemberton (Katharine Hepburn), a college athletics instructor, enters a number of golf matches against female professionals. She holds her own until her well-meaning but condescending fiancé, Collier Weld (William Ching), turns up at the games and distracts her. Sports manager Mike Conovan (Spencer Tracy) sees her talent and offers to train her. After realizing that Pat stops trying when Collier is around, Mike works to keep them apart -- especially when he begins to develop feelings for her.
ROMAN HOLIDAY (1953) STREAM NOW ON AMAZON
Being a princess is hard work, as Audrey Hepburn’s visiting royal ambassador will tell you. What she would not give to see the sights of Rome on her own like an anonymous civilian! So her highness plays hooky from her duties and pretends to be your average tourist. Enter reporter Gregory Peck, who takes kindness on this lost stranger … until he realizes who she is and smells a helluva scoop. You can keep your Breakfast at Tiffany’s — for us, this is the ultimate Hepburn movie, full of grace, wit, and some truly glorious footage of two movie stars tooling around the Italian city on a moped. Ask any visitor who’s ever stuck their hand inside the Bocca Della Verità — the film is genuinely iconic.
HOW TO MARRY A MILLIONAIRE (1953) STREAM ON AMAZON
A hilarious comedy about three man-crazed models out for eligible (and wealthy) bachelors who rent a posh Manhattan apartment and pose as rich gals in order to get their guys. Pola (Marilyn Monroe) is wooed by a playboy, but is snagged by a tax-dodging crook (David Wayne); Loco (Betty Grable) hooks on to a well-off Waldo (Fred Clark), but falls for a forest ranger (Rory Calhoun), and Schatz (Lauren Bacall) attracts an affluent widower (William Powell), but opts for the seemingly poor nice guy (Cameron Mitchell).
SABRINA (1954) STREAM ON AMAZON, HBOMAX
Humphrey Bogart, rom-com star? Sure, the man gave good banter with Lauren Bacall, but who would cast him opposite Audrey Hepburn and William Holden in a light, breezy love-triangle comedy? Billy Wilder saw something in Bogie that the rest of us did not, apparently, and thank god he did. The Roman Holiday actress plays the daughter of a rich family’s chauffeur, who’s pined for the family cad (Holden, natch) since she was a wee lass. After returning from Paris and looking like — well, like Audrey Hepburn in 1954 — the womanizer goes full Tex-Avery-wolf-eyes for her. His brother (Bogart) doesn’t want the young woman’s heart broken, so he pretends he’s in love with her … only to find that he doesn’t need to pretend after a while. Just watch this scene.
THE SEVEN YEAR ITCH (1955) STREAM ON AMAZON
In the midst of a summer heatwave, New Yorker Richard Sherman (Tom Ewell) ships his wife, Helen (Evelyn Keyes), and their son off to Maine for vacation. Left alone to work back in Manhattan, Richard encounters a gorgeous blonde model (Marilyn Monroe) who has moved into the apartment upstairs and becomes immediately infatuated. While pondering infidelity, Richard dreams of his beautiful new neighbor -- but will his fantasies about her become a reality?
FUNNY FACE (1957) STREAM ON AMAZON free for amazon prime members
Take two of the best actors in the biz, give them some showstopper musical numbers and gorgeous Givenchy 'fits, and you've got one remarkable film. Fred Astaire and Audrey Hepburn make magic on screen and you'll be humming George Gershwin's tunes, like the iconic "S'Wonderful," for days after the credits roll.
LOVE IN THE AFTERNOON (1957) STREAM ON AMAZON
French private investigator Claude Chavasse (Maurice Chevalier) discovers his client's wife has been having an affair with an American playboy, Frank Flannagan (Gary Cooper). When the client decides to kill Frank, Claude's sheltered daughter, Ariane (Audrey Hepburn), throws off the plan and saves his life. The two are instantly attracted to one another, but Ariane doesn't reveal her name. Frank then hires Claude to locate Ariane, unaware he has sent him on a mission to find his own daughter.
DESK SET (1957) STREAM ON AMAZON
Bunny Watson (Katharine Hepburn) is a library reference clerk stuck in a dead-end relationship with a boring television executive (Gig Young). Her life is thrown into turmoil when computer expert Richard Summers (Spencer Tracy) enters it. He has been assigned with automating her department, and she is fearful that Summers' new computers will automate her out of a job. She despises him at first, but eventually, each of the two starts to fall for the other's charms and strong personalities.
INDISCREET (1958) STREAM ON AMAZON
Famous theater actress Anna Kalman (Ingrid Bergman) has resigned herself to her single life, believing that she has missed her chance at meeting a husband. Weary of socializing in Europe, she returns to her London flat, where her sister Margaret (Phyllis Calvert) and diplomat brother-in-law Alfred (Cecil Parker) invite her to a banquet. She demurs until Alfred's banker friend, Philip Adams (Cary Grant), arrives and a flirtation begins. Their romance blossoms -- but he's already married.
PILLOW TALK (1959) STREAM ON AMAZON
Rock Hudson and Doris Day started their winning onscreen collaboration here, adeptly playing into their public personas: He’s Brad, a smug womanizer who shares a party line with Jan, a fussy, prudish career gal who doesn’t have time for love. Thanks to some wonderfully convoluted circumstances, however, a spark develops between them — although he has to disguise his voice so she doesn’t realize he’s the jerk on her phone. It’s not just the concept of a party line that makes Pillow Talk old-fashioned — its gender politics are rigidly mid-century, white-picket-fence conservative. But that cultural parochialism only gives the film’s subversive sexiness and combustible chemistry extra naughty delight. Underneath all that squeaky-clean innocence, there’s a whole lot of thirstiness.
SOME LIKE IT HOT (1959) STREAM NOW ON AMAZON
When Chicago musicians Joe (Tony Curtis) and Jerry (Jack Lemmon) accidentally witness a gangland shooting, they quickly board a southbound train to Florida, disguised as Josephine and Daphne, the two newest - and homeliest - members of an all-girl jazz band. Their cover is perfect...until a lovelorn singer (Marilyn Monroe) falls for "Josephine," an ancient playboy (Joe E. Brown) falls for "Daphne," and a mob boss (George Raft) refuses to fall for their hoax! Nominated for 7 Academy Awards, Some Like It Hot is the quintessential madcap farce and "one of the greatest of all film comedies"
THE APARTMENT (1960) STREAM NOW ON AMAZON
As C.C. Baxter, the most put-upon of all his put-upon characters, Jack Lemmon plays a white-collar drone so ineffectual that he loans out his apartment for his boss’s extramarital dalliances, pining for some up-the-corporate-ladder payout down the line. This is why he shares a kinship with Shirley MacLaine’s elevator operator, who’s also getting strung along by a two-timing executive. But it’s the contrast between his mania and her melancholy that holds Billy Wilder’s brilliant, winsome office comedy in balance — as if they’re hugging each other in the right direction. Just watch how Lemmon clowns around in a “junior executive” bowler hat and takes MacLaine’s holiday blues away. Out of miserable circumstances, the two lonelyhearts bond in their humor, resilience, and mutual insistence on dignity. It’s a match made in heaven, one floor at a time.
BREAKFAST AT TIFFANY’S (1961) STREAM NOW ON AMAZON
Speaking of NYC, the image of Audrey Hepburn clad in a black evening gown in front of Tiffany & Co. is one of the most recognizable scenes in movie history. The film also introduced audiences to Henry Mancini's sweet ballad "Moon River," which went on to win an Academy Award for Best Original Song. Admit it, you're humming already.
GUESS WHO’S COMING TO DINNER (1967) STREAM ON AMAZON
Spencer Tracy and Katharine Hepburn (who won the Academy Award for Best Actress for her performance) are unforgettable as perplexed parents in this landmark 1967 movie about mixed marriage. When Joanna Drayton (Katharine Houghton), a free-thinking white woman, and black doctor John Prentice (Sidney Poitier) become engaged, they travel to San Francisco to meet her parents. Matt Drayton (Spencer Tracy) and his wife Christina (Katharine Hepburn) are wealthy liberals who must confront the latent racism the coming marriage arouses. Also attending the Draytons' dinner are Prentice's parents (Roy E. Glenn Sr., Beah Richards), who vehemently disapprove of the relationship.
BAREFOOT IN THE PARK (1967) STREAM ON AMAZON, HBOMAX
Robert Redford and Jane Fonda star as a young newlywed couple who move into an apartment in New York City. Corie (Fonda) is care-free and spontaneous, which attracts the more serious, shy Paul (Redford). At first, their relationship is full of passion, but the pressure of living in a fifth-story walk-up that's falling apart starts to take a toll on their relationship. (Any couple who've ever lived together in a New York apartment can 100% relate.) They also have to deal with their wacky neighbors and a pestering mother-in-law. While the comedy can be a bit cheesy and dated at times, Redford and Fonda's sparkling chemistry leaps off the screen.
The Best Romantic Movies From the 80’s to Watch This Valentine's Day
Moving on to what some may consider classics as well - at least my children do - LOL! The movies of the 80’s are the movies from my youth! 80’s and 90’s movies are movies I say when I was in junior high, high school and college. They are the movies I saw with my friends and boyfriends. The movies that i most related with. I introduced a lot of these movies to my own children — and while my son thought Sixteen Candles was funny - he didn’t much like any other ones. My daughter, on the other hand, is as obsessed with 80’s movies as I am!! The Breakfast Club is her favorite movie!! AND, no modern-day list of Rom-Com’s would be complete without adding Meg Ryan and Reese Witherspoon!
SIXTEEN CANDLES (1984) STREAM NOW ON AMAZON
Anyone who's ever been an awkward teenager will cringe right along with this relatable rom-com. Samantha (Molly Ringwald) has a not-so-sweet 16th birthday, at which almost everything can go wrong. Luckily, all's well that ends well with one of the most iconic movie kisses on the books.
THE BREAKFAST CLUB (1985) STREAM NOW ON AMAZON
Five high school students from different walks of life endure a Saturday detention under a power-hungry principal (Paul Gleason). The disparate group includes rebel John (Judd Nelson), princess Claire (Molly Ringwald), outcast Allison (Ally Sheedy), brainy Brian (Anthony Michael Hall) and Andrew (Emilio Estevez), the jock. Each has a chance to tell his or her story, making the others see them a little differently -- and when the day ends, they question whether the school will ever be the same.
PRETTY IN PINK (1986) STREAM NOW ON AMAZON
John Hughes made teen comedies that had romantic elements in them (it was possible to forget at times that Sixteen Candles revolved around Sam pining for Jake Ryan amidst all the nerd shenanigans and that cringe-worthy Long Duk Dong thing). But this Hughes-penned movie — with Howard Deutch in the director’s chair — found just the right balance of funny, funky, heart-meltingly swoony and sweet. Wrong-side-of-the-tracks student Andie Walsh (Molly Ringwald, iconic) could never attract the attention of a rich prep like Blaine McDonaugh (Andrew McCarthy). What would their equally snobbish friends think? The ending is still enough to choke you up. And whenever things threaten to get too heavy, along comes Ducky in all his thrift-store-outfit, Otis-Redding-singing glory to crack you up. God bless you, Jon Cryer.
THE PRINCESS BRIDE (1987) STREAM NOW ON AMAZON, DISNEY+
This high fantasy, wry comedy, kick-ass swordfights, canny political commentary and, of course, sigh-inducing true love. As we follow reluctant damsel Buttercup (Robin Wright) and farmboy-turned-pirate Westley (Cary Elwes) up the Cliffs of Insanity, through the Fire Swamp, and to the very edge of death, we’re simultaneously rooting for our lovers to win the day and chuckling at the knowingly trope-tweaking silliness of it all. Plus unlike the ailing grandson (Fred Savage) in the framing story, we are most definitely not grossed out by the kissing parts.
CAN’T BUY ME LOVE (1987) STREAM ON AMAZON , HBOMAX
Before Patrick Dempsey was McDreamy, he was Ronald Miller, a nerd who pays his next-door neighbor and popular cheerleader Cindy (Amanda Peterson) $1,000 to pretend to go out with him to increase his clout among their high school classmates. Cindy's in a financial predicament because she has to replace her mom's fancy outfit she ruined after borrowing it without permission, so she takes him up on the offer. Get ready for big hair, classic '80s music, and Dempsey stealing your heart while riding a lawnmower.
MOONSTRUCK (1987) STREAM NOW ON AMAZON, YOUTUBE
Casting “crazy” Nicolas Cage as a romantic lead may seem absolutely loony. But that’s partially why Moonstruck still feels so charming: It’s a mature love story that explains why it’s sometimes right to fall for Mr. Wrong. Cher is Loretta Castorini, a cautious Italian-American widow all set to get remarried to a bland fella. Then guess who has her heart stolen by his surly one-handed sibling, played by you-know-who? And who knew these actors would fit so well together? It’s a movie that has both the ring of seen-it-all truth and the atmosphere of a fairytale-like a Dean Martin song come to life. “Snap out of it!”
BULL DURHAM (1988) STREAM ON HULU, AMAZON
In Durham, N.C., the Bulls minor league baseball team has one asset no other can claim: a poetry-loving groupie named Annie Savoy (Susan Sarandon). As the team's season begins, Annie selects brash new recruit Ebby Calvin Laloosh (Tim Robbins), whom she christens "Nuke," to inspire with the religion of baseball. Nuke also receives guidance from veteran player Crash Davis (Kevin Costner), who settles Nuke's erratic pitching and teaches him to follow the catcher's lead.
SAY ANYTHING (1989) STREAM NOW ON AMAZON, HULU
One of the most tender teen comedies in the canon: Lloyd Dobler (John Cusack) set the stage for high-school boys to be more than a heap of hormones. Seriously, who could have played this sweet, boom box-toting antidote to dude-bros, i.e. the knuckleheads hanging out at the Gas ‘n’ Sip pontificating about the opposite sex? Described as “basic” by brainy, beautiful Diane Court (Ione Skye), our underachieving hero nonetheless wins her heart … only to get his broken. Both Skye and Cusack bring such raw, physical emotion to their performances that the story easily evolves beyond strict rom-com. It’s still funny — just yell “You. Must. CHILL!” in your best Dobler voice and try not to laugh. But ultimately, it’s their young love that’s as satisfying as the ding after a plane takes flight.
WHEN HARRY MET SALLY (1989) STREAM NOW ON AMAZON, HBOMAX
The Attraction Theory. The bookstore encounter. The New Year’s Eve admission of love. The vignettes of older couples recounting their relationship stories. “You made a woman meow?!” The split-screen phone call involving Carrie Fisher and Bruno Kirby’s best friends. The deli scene — dear god, that deli scene. Chances are good that when you hear the phrase “rom-com,” Rob Reiner’s movie — about two longtime acquaintances who finally realize the only people that are truly right for them is each other — was the first title you thought of. Yes, it owes a good deal to Annie Hall in its tenor and tone, but what Billy Crystal and Meg Ryan do with these roles is sui generis; it’s one-of-a-kind alchemy. And anyone who does not think Nora Ephron was as great a screenwriter as she was an essayist simply isn’t paying attention. It is the one rom-com to rule them all, a perfect distillation of the form. We’ll always have what they’re having.
The Best Romantic Movies From the 90’s to Watch This Valentine's Day
PRETTY WOMAN (1990) STREAM ON AMAZON
In this modern update on Cinderella, a prostitute, and a wealthy businessman fall hard for one another, forming an unlikely pair. While on a business trip in L.A., Edward (Richard Gere), who makes a living buying and breaking up companies, picks up a hooker, Vivian (Julia Roberts), on a lark. After Edward hires Vivian to stay with him for the weekend, the two get closer, only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.
GROUNDHOG DAY (1993) STREAM ON AMAZON
Phil (Bill Murray), a weatherman, is out to cover the annual emergence of the groundhog from its hole. He gets caught in a blizzard that he didn't predict and finds himself trapped in a time warp. He is doomed to relive the same day over and over again until he gets it right.
REALITY BITES (1993) STREAM ON AMAZON
After college, Lelaina (Winona Ryder) films a documentary about herself and friends as they flounder in their attempts to forge relationships and begin careers. Vickie (Janeane Garofalo) works retail, has an endless string of one-night stands and awaits the results of her HIV test. Sammy (Steve Zahn) tries to come out to his parents. Lelaina gets involved with yuppie Michael (Ben Stiller) while maintaining a love-hate relationship with Troy (Ethan Hawke), who's undergoing an existential crisis.
SLEEPLESS IN SEATTLE (1993) STREAM NOW ON AMAZON
It’s the rare rom-com that has the audacity to keep its two would-be lovers apart until the closing moments of the movie, but leave it to her royal highness Nora Ephron to make the gimmick work — and work brilliantly. The setup is pure Nineties missed connection: On Christmas Eve, newspaper reporter Annie (Meg Ryan) finds herself drawn to a widower (Tom Hanks) who she hears on a call-in radio show. She slowly becomes obsessed with tracking him down and arranging an Affair to Remember-inspired meeting — despite the fact that he lives clear on the other side of the country and doesn’t even know she exists. As Sleepless in Seattle plays out, the viewer becomes as invested in the idea of these two folks finding each other as Annie is. The fact that we’re essentially watching the story of a stalker pursuing her prey and rooting for her the whole way is a testament to both Ephron’s writing and to Ryan’s unassailable charm.
AS GOOD AS IT GETS (1997) STREAM ON AMAZON (for free) NETFLIX
Melvin Udall (Jack Nicholson) is an obsessive-compulsive writer of romantic fiction who's rude to everyone he meets, including his gay neighbor Simon (Greg Kinnear), but when he has to look after Simon's dog, he begins to soften and, if still not completely over his problems, finds he can conduct a relationship with the only waitress (Helen Hunt) at the local diner who'll serve him.
YOU’VE GOT MAIL (1998) STREAM NOW ON AMAZON, HBOMAX
Some of the technology in this late '90s standard might be a tad dated, but the message still lands. Tom Hanks and Meg Ryan have starred in three films together, but You've Got Mail is our favorite for the way it makes the most of their infectious onscreen chemistry.
CHASING AMY (1997) STREAM ON AMAZON, NETFLIX, HBOMAX
Holden and Banky are best friends and authors of a popular comic book. Holden falls in love with Alyssa, who happens to be a lesbian. Holden's relationship with Alyssa strains his life-long friendship with Banky, and soon the relationship between Holden and Alyssa has problems when he cannot deal with her past.
10 THINGS I HATE ABOUT YOU (1999) STREAM NOW ON AMAZON, DISNEY+
A modern update on Shakespeare's The Taming of the Shrew, this teen flick pairs angsty Julia Stiles with charming Heath Ledger for a high-school romance that set the standard for so many of our real-life crushes. We dare you not to swoon while watching Ledger performing "I Can't Take My Eyes Off Of You."
The 13 Best Modern Day Romantic Movies to Watch This Valentine's Day
HIGH FIDELITY (2000) STREAM ON AMAZON, HBOMAX
Rob Gordon (John Cusack) is the owner of a failing record store in Chicago, where he sells music the old-fashioned way -- on vinyl. Although they have an encyclopedic knowledge of pop music and are consumed by the music scene, it's of no help to Rob, whose needle skips the love groove when his long-time girlfriend, Laura (Iben Hjejle), walks out on him. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.
SAVE THE LAST DANCE (2001) STREAM ON AMAZON
Sara (Julia Stiles) is moved from a small Midwestern town to the south side of Chicago when her mother dies in a car accident and must live with her father. She soon falls for an African American teenager (Sean Patrick Thomas) at her new high school and he has less than an idyllic past. They share a love for dance (ballet and hip hop respectively) and together they tackle the problems that go with an interracial relationship.
SERENDIPITY (2001) STREAM NOW ON AMAZON, HBOMAX
Jonathan (John Cusack) and Sara (Kate Beckinsale) spend one amazing night together in New York City, but then lose track of each other for years afterward. As they both get ready to marry other people, they develop a case of cold feet and search for one another instead. If you don't believe in fate, you will by the end.
KATE & LEOPOLD (2001) STREAM ON AMAZON, NETFLIX
Kate McKay (Meg Ryan) is a modern-day executive, a 21st-century woman driven to succeed in the corporate world. Leopold, the third Duke of Albany, is a charming gent and bachelor of the late 18OOs. With the career and social expectations looming, each has grown cynical about the very notion of falling in love. But when a rip in the fabric of time thrusts Leopold into present-day New York, the potential for an old-fashioned modern romance ignites.
MY BIG FAT GREEK WEDDING (2002) STREAM ON AMAZON, HULU, HBOMAX
Everyone in the Portokalos family worries about Toula (Nia Vardalos). Still unmarried at 30 years old, she works at Dancing Zorba's, the Greek restaurant owned by her parents, Gus (Michael Constantine) and Maria (Lainie Kazan). After taking a job at her aunt's travel agency, she falls in love with Ian Miller (John Corbett), a teacher who is tall, handsome and definitely not Greek. Toula isn't sure which will be more upsetting to her father, that Ian is a foreigner or that he's a vegetarian.
SWEET HOME ALABAMA (2002) STREAM ON AMAZON
New York fashion designer Melanie (Reese Witherspoon) suddenly finds herself engaged to the city's most eligible bachelor. But Melanie's past holds many secrets, including Jake (Josh Lucas), the redneck husband she married in high school, who refuses to divorce her. Bound and determined to end their relationship once and for all, Melanie sneaks back home to Alabama to confront her past, only to discover that you can take the girl out of the South, but you can't take the South out of the girl.
13 GOING ON 30 (2004) STREAM ON AMAZON, HBOMAX
A girl who's sick of the social strictures of junior high is transformed into a grownup overnight. In this feel-good fairy tale, teenager Jenna (Christa B. Allen) wants a boyfriend, and when she's unable to find one, she fantasizes about being a well-adjusted adult. Suddenly, her secret desire becomes a reality, and she is transformed into a 30-year-old (Jennifer Garner). But adulthood, with its own set of male-female challenges, isn't as easy as it looks.
MAMMA MIA! (2008) STREAM ON AMAZON, HULU
It's nearly impossible to watch this flick without dancing around your living room to all the great ABBA tunes. Sophie (Amanda Seyfried) has invited three men who might be her father to her wedding but hasn't told her mom Donna (Meryl Streep). To absolutely no one's surprise, Donna doesn't love reuniting with her old flings – Sam (Pierce Brosnan), Harry (Colin Firth), and Bill (Stellan Skarsgård). All sorts of musical hilarity ensue.
SILVER LININGS PLAYBOOK (2012) STREAM ON AMAZON, NETFLIX
After losing his job and wife, and spending time in a mental institution, Pat Solatano (Bradley Cooper) winds up living with his parents (Robert De Niro, Jacki Weaver). He wants to rebuild his life and reunite with his wife, but his parents would be happy if he just shared their obsession with the Philadelphia Eagles. Things get complicated when Pat meets Tiffany (Jennifer Lawrence), who offers to help him reconnect with his wife, if he will do something very important for her in exchange.
ENOUGH SAID (2013) STREAM NOW ON AMAZON
Tony Soprano as a romantic lead? ‘Nuff said. Nicole Holofcener made us see James Gandolfini in a different light with this quietly moving film, co-starring Julia Louis-Dreyfus as a massage therapist who learns the man she’s seeing is the ex-husband of her new client (Catherine Keener). Holofcener has a soft touch with even the spikiest material, making it feel lived-in and comfortable, and Enough Said might be the coziest of all her films. It’s not that often that we get a rom-com featuring middle-aged characters, and there’s a real tenderness that Holofcener evokes here, capturing the soft side of Gandolfini in a genuinely sweet film.
THE BIG SICK (2017) STREAM ON AMAZON (free with Amazon Prime)
Kumail is a Pakistani comic, who meets an American graduate student named Emily at one of his stand-up shows. As their relationship blossoms, he soon becomes worried about what his traditional Muslim parents will think of her. When Emily suddenly comes down with an illness that leaves her in a coma, Kumail finds himself developing a bond with her deeply concerned mother and father.
CRAZY RICH ASIANS (2018) STREAM NOW ON AMAZON, HULU, HBOMAX
Manhattan econ professor Rachel Chu (Constance Wu) knew that her guy Nick Young (Henry Golding) came from money...but when she accompanied him home to Singapore for the wedding of his best friend (Chris Pang), she wasn’t prepared for the eye-popping extent of the family wealth--or for the cold shoulder forthcoming from Nick’s domineering and disapproving mom (Michelle Yeoh). Hit rom-com take on the Kevin Kwan novel co-stars Awkwafina, Gemma Chan, Ken Jeong, Jimmy O. Yang.
That about does it for my BEST Romantic Comedy Movies. I mean, I could have included another 58 titles really. Literally, there are so many great Rom-Coms out today from the past 100 years. This list could easily have included 200 titles of the Best Romantic Comedy Movies to Watch this February for Valentine’s Day. (but I really don’t have time to list them all - lol!!) Did I forget any important ones? Let me know!
