Category Archives: Romantic Comedy

Flying Down to Rio (1933)

We can still wistfully recall the days when, in the movies at least, developing world vacation spots were playgrounds for rich people who dressed in tuxedos and gowns, danced, ballroom style, under the palm trees, and nuzzled in the equatorial moonlight. Flying Down to Rio introduced the pairing of Fred Astaire and Ginger Rogers (but as the second leads, after Dolores Del Rio and Gene Raymond), and it features splendid tunes (by Vincent Youmans and lyricists Gus Kahn and Edward Eliscu) and a good amount of pre–Production Code bralessness—all under a fake Brazilian sky.

Film screenshot from the trailer to Flying Dow...
Film screenshot from the trailer to Flying Down to Rio (1933) announcing the screen partnership of Fred Astaire and Ginger Rogers (Photo credit: Wikipedia)

Mr. & Mrs. Smith (1941)

Every pair of married lovebirds has to ask: if you had to do it all over, would you get married again? The luminescent Carole Lombard asks Robert Montgomery that very question and he responds “no,” leaving us all to wonder if his eyes, brain, and loins are still in functioning order. It turns out that a paperwork glitch grants him his wish—they’re not legally wed after all, and Carole hands him his hat in high dudgeon, giving him no choice but to woo her back. It certainly seems improbable that this marital conundrum is brought to you by cynical master Alfred Hitchcock, but we should be so lucky as to still have romantic comedies like this: you haven’t seen anything until you’ve seen Montgomery try to punch himself in the nose, or Lombard handle acres of prime slapstick dialogue with the fierce energy of a tornado. A caveat: Mr. & Mrs. Smith is an anniversary movie only for those who would answer that question—“Would you marry me all over again?”—with an emphatic yes. Otherwise, your yearly celebration of conjugal bliss might end in separate bedroom assignments.

Cropped screenshot of Robert Montgomery and Ca...
Cropped screenshot of Robert Montgomery and Carole Lombard from the trailer for the film Mr. & Mrs. Smith (Photo credit: Wikipedia)

The Awful Truth (1937)

A movie about a couple in the midst of a divorce may seem an odd choice for an anniversary movie, but this is the antiromantic romance, marriage as ping-pong, and one of the preeminent screwball comedies. Director Leo McCarey and timeless stars Cary Grant and Irene Dunne are virtually without peer in handling sparkling dialogue. Even when they’re actively destroying each other’s lives in bouts of schadenfreude, they’re entertaining—and the characters (embodying 1930s Hollywood’s excellent idea of a healthy marriage) are just as addictively entertaining to each other, as well. The Awful Truth isn’t the choice for couples who want to moon at each other over candlelight, but if you’ve seen enough road to find laughs at each other’s expense, it’s essential viewing.

Cover of "The Awful Truth"
Cover of The Awful Truth

The Thin Man (1934)

An eccentric inventor disappears and there’s no shortage of suspects, from his tawdry girlfriend to his ex-wife’s deadbeat husband. There’s a Dashiell Hammett mystery at the bottom of this movie, but it’s inconsequential—what this dishy lark is really about is the enthralling banter between the most debonair, comfortably droll, mutually secure movie couple of all time, Nick and Nora Charles (William Powell and, in a career-making turn, the delectable Myrna Loy). The Thin Man is an anniversary movie for those who don’t want romance and sentiment; these two are past that stage, and instead they make marriage look fun, from Loy’s dismissive nose shrug to Powell, hungover, shooting at Christmas ornaments while reclined on the sofa (“Best Christmas present I ever got!”) to fur-trimmed dressing gowns and flowing martinis. Movies haven’t dared to portray this kind of grown-up relationship too often, and this one made stars of its leads. But the secret of it is that this is romance, too—there are no moony gazes or clinches, but it’s evident to the blind that the Charleses, however they may snipe and gripe, are terribly, splendidly in love, and that they enjoy each other like sunny days.

Cropped screenshot of Myrna Loy from the trail...
Cropped screenshot of Myrna Loy from the trailer for Another Thin Man (Photo credit: Wikipedia)

Topper (1937)

If you’ve been wondering why in this day and age, when Hollywood seems to be doing nothing but recycling old movies, no one has thought to remake Topper, consider this: it’s essentially a story in which driving drunk at breakneck speed around dangerous curves with your feet on the steering wheel of a convertible is seen as not just funny, but also as a paradigm for living the good life. Party animals George and Marian Kerby (Cary Grant and Constance Bennett, bouncing screwball dialogue like Ping-Pong champs) become ghosts because of such antics, and they soon learn they’ve got a pretty short resume for applying for residence in Heaven. They set out to do a good deed: loosening up repressed bank president Cosmo Topper (Roland Young), who is henpecked by his propriety-conscious wife and who leads as dull a life as you can imagine. A kind of morality-tale act of retribution on Roaring Twenties hedonism, Topper is also completely 1930s in its battery of platinum blondes in slinky sequined evening dresses, men in tuxes and top hats driving roadsters, bankers in fedoras, and dancing in nightclubs.

Tin Cup (1996)

Ron Shelton’s making his incisive way through the major sports (let’s hope he hasn’t given up before getting to boccie), and here he rampages across the green with Kevin Costner’s gone-to-seed golf rogue, who’s trying to qualify for the U.S. Open in order to impress Rene Russo. Because it’s Shelton, Tin Cup is probably the most faithful movie ever made about the game, even if it’s too long and Costner’s aging rapscallion pales after a while.

Cover of "Tin Cup"
Cover of Tin Cup

Pat and Mike (1952)

Cover of "The Hepburn & Tracy Signature C...
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Katharine Hepburn is a pro golfer, Spencer Tracy is her promoter, and Garson Kanin and Ruth Gordon’s screenplay gives them helping after helping of gender-combat banter, on and off the course (we’re treated to the sight of Hepburn herself, in a championship game, hitting against legendary real-life pro Babe Didrikson Zaharias, who was the subject of the 1975 TV movie Babe). Pat and Mike is perhaps the best of the Hepburn-Tracy comedies—because here, Tracy doesn’t always get the upper hand.

Bull Durham (1988)

There’s no other sport that inspires more emotion, rumination, and heartfelt worship than baseball, and Ron Shelton’s signature Bull Durham embodies all of these in one perfect, life-loving swoop. This slice of minor-league life remains lovable because there are no big-headed major-league egos around—just the fervent hoping to get there. No underdog triumphs, no sentimental formulas, and no baloney to be found—from Tim Robbins’s talented jerk to Susan Sarandon’s small-town groupie who’s dizzy with big-city ideas to Kevin Costner’s career-anchoring performance as the aging catcher who shoulders the responsibility of molding the uncontrollable pitcher into a star even as his own dreams of the majors sail further out of reach. The script crackles with educated wit, the minor characters are just as funny and original as the main players, and the homage to baseball is everything it should be: heartbreaking in some ways, but crazy for the game, for summer evenings, and for retaining a fiery sliver of youth deep into the middle years.

Say Anything . . . (1989)

Remember when you spent all your years of high school yearning after that one person, despairing of ever having him or her realize you exist? That’s just what happens to Lloyd Dobler (John Cusack). Fortunately, after graduation, she does notice him, and they spend the summer dancing around the possibility of falling deeply in love.  Cameron Crowe‘s Say Anything goes a long way just on charm, from Cusack’s diffident-yet-deeply-ethical everyman quality to Lili Taylor’s awful guitar-strummed songs about lost love, to the pack of nowhere boys (including Jeremy Piven) hanging out at the local Gas ’n Sip and philosophizing about women they know nothing about. Ignore the secondary plot, about Diane’s possibly shady father, and savor the whiff of teenage desires anxiously fulfilled.

Serendipity (2001)

John Cusack and Kate Beckinsale meet during a holiday shopping tug-of-war for a pair of cashmere gloves at Bloomingdale’s and continue their flirting over the famous frozen hot chocolate at nearby Serendipity 3, following up with skating in the snow at Wollman Rink. Is it fate? She thinks so, to an almost psychotic degree, and so decides to test it, and thus the movie carries on through several years and many monstrous dalliances with destiny before the inevitable hookup.

Cover of "Serendipity"
Cover of Serendipity
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Shakespeare in Love (1998)

A lighthearted and lovely tale of Shakespeare’s own unrequited love story, which proved the inspiration for both Romeo and Juliet and Twelfth Night, as light on its feet as Romeo and Juliet is weighty with tragedy. The comic timing from a large and buoyant cast is impeccable, and the lovable energy of the movie is embodied in Shakespeare himself (Joseph Fiennes), who never seems to sleep and is in constant athletic motion. The players, sometimes in disguise, deliver masses of Shakespearean dialogue with complete conviction, wit, and speed, and there’s enough heat between Fiennes and Oscar winner Gwyneth Paltrow to warm the home fires.

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Sleepless in Seattle (1993)

There’s Romance with a capital R in so many aspects of this movie that you can overlook some of the more toxic Nora Ephron–esque things about it, including insufferably precocious children and scenes that seem to be built entirely of one-liners. Sam (Tom Hanks) and Annie (Meg Ryan) are both adorable and lovable: he, a grieving widower raising his son alone, bravely, on the watery banks of Seattle; she, beautiful, smart, and not quite willing to give up every woman’s fantasy that “there’s one guy out there for me, and he isn’t a man who wears a bow tie.” The homage to 1957’s An Affair to Remember can only mean we’re bound to see the Empire State Building sooner or later, but, arguably, the most memorable scene (stolen by Rita Wilson, the real-life love of Hanks’s life) is a bright exchange about our attachments to certain movies and the way we love to shamelessly weep over them.

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Heaven Can Wait (1978)

Warren Beatty’s remake of 1941’s pretty swell Here Comes Mr. Jordan is a wonderfully lighthearted love story of an aging quarterback who is plucked up to Heaven’s way station before his time—and before his final Super Bowl. Too late to go back among the living as his old self, he gets temporary custody of a millionaire’s body, becoming smitten with an Englishwoman (Julie Christie) in the bargain. Beatty and codirector Buck Henry cut the sweetness with plenty of satire, and Charles Grodin all but steals the show with his special brand of duplicitous diffidence. Hardly a moment in the movie that isn’t a pleasure.

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Ninotchka (1939)

This Ernst Lubitsch comedy is pure bliss, and a paean to Parisian mad love and fun, which hedonistic American expat Melvyn Douglas pitches to steely, humorless Soviet comrade Greta Garbo, who’s in town on a matter of state business (to reel in a few goofy Soviet agents who have become distracted by the Gallic pleasure principle). Of course, Garbo is masterful as the comically grim maiden in a gray suit, barely disguising a warm heart and yearning for love that we can always see beating beneath the Marxist-Leninist ideology. A little champagne, a little Paris skyline, a little woo from the rather satyric Douglas, and she opens like a lily (figuratively speaking, at least; this is 1939). It doesn’t hurt that Lubitsch had the subtlety and timing of a Hollywood Mozart, or that Ninotchka’s screenplay, penned mostly by Billy Wilder and Charles Brackett, is one of the wittiest and gentlest of Hollywood’s entire golden age.

Meet the Parents (2000)

Meet the Parents (soundtrack)
Meet the Parents (soundtrack) (Photo credit: Wikipedia)

This brutally comic hit found the lurking fears of all young lovers who are meeting their prospective in-laws for the first time—and lit them up good. Ben Stiller is just, well, Ben Stiller, but Robert De Niro, as the fiancée’s father, shines: much more than just a controlling, disapproving patriarch, he’s actually a semiretired CIA ramrod, with only his little girl now to serve and protect. Every step Stiller makes is the wrong step; every action is scrutinized mercilessly. Stiller’s anxious gaze of disbelief as each new mishap befalls him is a wonder, and De Niro flexes all of his dead-eyed menace.

My Best Friend’s Wedding (1997)

Film poster for My Best Friend's Wedding - Cop...
Film poster for My Best Friend’s Wedding – Copyright 1997, Sony Pictures (Photo credit: Wikipedia)

The question of whether or not men and women can be true friends without being romantically involved is put to the test when Dermot Mulroney tells best friend Julia Roberts that he’s getting married—and, by the way, it’s this weekend, so please fly out to celebrate the nuptials. Nothing ever looks so good as it does after it’s slipped from your grasp, so our heroine pulls out the underhanded stops to try to win him. Eccentric and campy, the fete includes Cameron Diaz, in full bloom, and the irrepressible Rupert Everett rescuing the day more than once.

Miami Rhapsody (1995)

This effervescent, if very Woody Allen–like, comedy from writer-director David Frankel (who would go on to make 2006’s The Devil Wears Prada) poses a particular quandary for its east-coast-Florida-Jewish heroine (Sarah Jessica Parker): how to be ecstatic about getting engaged when everyone around you is cheating. Each of her parents (Mia Farrow and Paul Mazursky) is embroiled with someone else; her newly married sister (Carla Gugino), desperate for the attention she doesn’t get from her jock husband, beds an old boyfriend, while her brother (Kevin Pollack) cheats on his very pregnant wife. Is there something wrong with the Florida water, other than sulfur and chlorine? The incisive jokes and deliveries (Parker has never been so good, before or since) make a good case for remaining uncommitted, so anyone whose toes are getting a little frosty should be careful.

Four Weddings and a Funeral (1994)

A band of single friends, led by the shyly charming Hugh Grant, chase each other around England, attending weddings in various states of disarray and embarrassment. Star-crossed amour and funny wedding mishaps abound, but this international smash sucked in both its audience and an Oscar nomination with the grace of its execution, a brilliantly witty screenplay—perfectly staged and acted—and a pervasive fondness for even the bit characters and background extras.

Honeymoon in Vegas (1992)

Commitment-phobe Nicholas Cage loses a Vegas poker game to a cunning gambler (James Caan) who offers a devil’s bargain: the debt is forgiven in exchange for a weekend with the loser’s fiancée (Sarah Jessica Parker). Nicholas Cage is at his frenetic best as the desperate bridegroom trying to win back the girl, if only he can find her—and be on the lookout for Peter Boyle in a hilarious cameo. Deftly written and directed by Andrew (The In-Laws) Bergman, this is for anyone who chooses to skip the traditional wedding in favor of the quickie hitch at the Elvis Chapel of Love.

True Love (1989)

Nuptial planning, Bronx-Italian style, including tacky, rainbow-colored bridesmaid gowns, tawdry wedding halls that serve mashed potatoes dyed to match the color of the gowns, opinionated friends, interfering relatives, and a bride and groom who are swept along with the idea of marriage as something you ought to do, and so convince themselves that they want to do it. Ron Eldard’s groom is hopelessly immature and unromantic; Annabella Sciorra’s bride ignores the fact that her marriage is doomed before it starts (she can’t help it—she’s too busy wiping fingerprints off her back). You’ll probably find this movie a lot funnier if you’ve witnessed this type of New Yawk behavior up close; otherwise, it may all just seem completely crazy.

Moonstruck (1987)

Romance and Italiante comedy abound in a kind of dreamy, magical hunk of brownstone Brooklyn, with Cher’s widowed frump dubiously accepting the proposal of Danny Aiello’s dumb mama’s boy, then falling for his troubled, one-handed brother (Nicolas Cage). Luckily, the margins of the movie are filled to the brim with witty character actors, slabs of comedic nonsense, behavioral detail, and a sense of warmheartedness in regard to the follies of humankind. Screenwriter John Patrick Shanley captured a cartoon-paisan flavor; though it seems somewhat dated now, it’s a far better submersion in Mediterranean-emigré boisterousness than My Big Fat Greek Wedding.

Moonstruck (Photo credit: Wikipedia)


The Philadelphia Story (1940)

A famous pre-nup crash and burn: Katharine Hepburn is the proud, self-righteous bride to be who wants to be knocked down from her pedestal (“I don’t want to be worshiped; I just want to be loved”); Cary Grant is the sarcastic ex who’s determined to make her feel guilty and stop the wedding; Jimmy Stewart is the class-conscious society reporter thrust into the maelstrom. General wedding-planning tizziness abounds. The comedy is high, and the racehorses in this stable all run in peak form—even if the thrust of the movie seems to be that women should forgive men their boyish faults, whether they include drinking, adultery, or just the pinching fingers of the slightly creepy Uncle Willie (Roland Young). Though overrated, this may be a good movie to watch before making or accepting a marriage proposal, if only because it stirs up every doubt and second thought you should have before tying the knot.

Cropped screenshot of the film The Philadelphi...
Cropped screenshot of the film The Philadelphia Story (Photo credit: Wikipedia)

The Imposters (1998)

After the 1930s, the luxury-ship-stowaway comedy fell, more or less, into remission until Stanley Tucci (who wrote, directed, and stars here) concocted this happy vaudeville about two lousy thespians (Tucci and Oliver Platt) who find themselves, quite by accident, on a cruise ship among European anarchists, spies, grieving ex-royalty, a pompous theater star (Alfred Molina), a suicidal nightclub singer named Happy Franks (Steve Buscemi), and sundry other broadly played types (including a Nazi-esque ship officer, triumphantly personified by Campbell Scott). It’s so unpretentious and dizzy, the entire cast conga-lines right off the set at the end, to boppin’ tango music.

The Lady Eve (1941)

The Lady Eve
The Lady Eve (Photo credit: Wikipedia)

Even if you’re the type who gets seasick in a wading pool, there’s something undeniably alluring about a 1940s cruise-ship liaison, and you’re not going to find a cuter and funnier dynamic than Barbara Stanwyck in a midriff-baring dress purring “Why, Hopsy!” at befuddled millionaire Henry Fonda. She’s part of a cardsharp trio out to fleece rich suckers, and he’s the chump. Preston Sturges wrote the devil out of this fluff in his customary fashion, and it might feature the hugest studio-built luxury boat ever dreamed up, with mansion-like ballrooms, sumptuous banquets, and endless moonlit decks.

Fever Pitch (2005)

Fever Pitch (2005 film)
Fever Pitch (2005 film) (Photo credit: Wikipedia)

Perhaps date movies shouldn’t be about people who are dating at all, since films that focus on relationship strife provoke questions of rights and wrongs, guilt and innocence that viewers on a date might not want to get into. At least Fever Pitch (which is based on a much more cynical Nick Hornby novel that revolves around English football, not baseball) is relatively innocuous in this regard, if only because the main characters are both so adorable: Late Night TV favorite Jimmy Fallon is Ben, a humble schoolteacher who loves his job and the Boston Red Sox; Drew Barrymore is Lindsey, a high-powered business genius who’s looking for something better than the shallow corporate climbers she usually dates. Trouble occurs when she starts realizing that Ben just might not consider her as important as a bunch of overpaid jocks. (Note to male viewers: the correct response to this realization is not, “Yeah, so?”) The movie includes cameos by some of the 2004 Sox—who beat the odds and earned Boston a World Series victory for the first time in eighty-six years. (The last scenes of the film were rewritten and shot during the series to capitalize on this amazing turn of events—who coulda thunk it?).