May 6 2011 3:06pm

I Love New York: Top 10 New York-Based Romantic Comedies

Ginnifer Goodwin and Colin Egglesfield in Something BorrowedBased on Emily Giffin’s 2004 novel, the new movie Something Borrowed opens in theaters today. The story of a lovelorn New Yorker who has it bad for her best-friend’s fiancé, it stars romantic comedy stalwarts Ginnifer Goodwin and Kate Hudson, as well as the goofy, indefinable charm of The Office’s John Krasinski. (Also, there’s some dude named Colin Egglesfield, whose name was unfamiliar, but whom I now realize I know from his work in the ill-fated Melrose Place reboot and his role in the equally disastrous Vampires: The Turning.)

The “lovelorn New Yorker” part of the equation is nothing new, of course; indeed, out of all the myriad genres of film, it seems like romantic comedies are more likely to be set in the city that never sleeps than anywhere else. Sure, San Francisco has seen its share of lovers united; L. A., Boston and Chicago, too. Seattle has gotten some action, and every now and then we’ll take a trip down South to find genteel wooing among the plantations and suchlike. But in the main, New York’s fabled streets are apparently paved with soul mates, and with yet another Big Apple-based love story all primed to wow the Mother’s Day weekend crowd, I thought I’d take a look back at the best of those that have come before…

Loser10. Loser (2000)
Written and Directed by Amy Heckerling

Clueless and Fast Times at Ridgemont High director Amy Heckerling has long been unfairly maligned for her work on this college-based love story, but I have to disagree emphatically. Our “loser” is the kind-hearted small town scholarship kid Paul (Jason Biggs) who falls for adorably goth-esque Everclear fan Nora (Mena Suvari)….except that she’s secretly dating her professor (Greg Kinnear). Set in and around NYU, perhaps the film’s most memorable sequence is when these two crazy kids head out for a day in Manhattan; their goal being to not spend a cent. They manage it, too. Sure, there’s petty larceny involved, but it’s still very cute, funny and sweet—as is this movie.

Two Weeks Notice9. Two Weeks Notice (2002)
Written and Directed by Marc Lawrence

At the beginning of the utterly delightful punctuation primer Eats, Shoots and Leaves, author and semanticist Lynne Truss recounts her time protesting outside the London premiere of this movie, holding up a sign supplying the title’s missing apostrophe. Poor literacy aside, however, this is a movie in which Sandra Bullock and Hugh Grant do what they do best, and that best is pretty damned good: she is a crusading environmental lawyer, he a dilettante playboy property magnate, and after blackmailing her into becoming his personal attorney, love blooms among the barbs. The result is an agreeable romp that offers up two rom-com stars in their prime and, as an added bonus, pays tribute to Coney Island.

Splash8. Splash (1984)
Written by Lowell Ganz
Directed by Ron Howard

This is the movie that launched Tom Hanks to stardom, and was among Ron Howard’s first forays behind the camera. When New York grocer Allen (Hanks) is saved from drowning by a mermaid (Daryl Hannah), the result is a magical and quite literal fish-out-of-water tale that sees the mythical beauty walking the streets of New York (and even being named after one, which is doubtless to blame for the grades full of little girls named Madison in today’s elementary schools). Funny, sweet, fantastical and quirky, more than 25 years on Splash is still the pinnacle of all aquatic-based romantic comedies. (And, yes, that is saying something.)

Kissing Jessica Stein7. Kissing Jessica Stein (2001)
Written by Jennifer Westfeldt and Heather Juergensen
Directed by Charles Herman-Wurmfeld

Neurotic doesn’t begin to describe copy editor Jessica Stein (Jennifer Westfeldt). Nearing thirty and the despair of her managing mother (Tovah Feldshuh), a run of unsuccessful dates and the serendipitous choice of a favorite quote has Jessica answering the Classified ad of bi-curious vixen Helen (Heather Juergensen). The two start a tentative romance—made problematic by Jessica’s intense fear of the unconventional (in addition to her not really being gay)—while the disdainful attitude of Jessica’s ex-boyfriend and current boss Josh (Scott Cohen) can only mean one thing. This movie is witty, engaging, playful, romantic and, ultimately, a surprise… although it may not surprise you to learn that Jessica (whose Judaism is a topic of much discussion) is, of course, from Scarsdale.

It Could Happen to You6. It Could Happen to You (1994)
Written by Jane Anderson
Directed by Andrew Bergman

Loosely based on real life events, this film sees New York City policeman Charlie (Nicholas Cage), short of cash for a tip, promise to split his winnings with waitress Yvonne (Bridget Fonda) if his numbers should come up in that night’s lottery draw. They do, and of the two million dollars he and his rapacious wife Muriel (Rosie Perez) subsequently win, he gives Yvonne exactly half, much to the tabloids’ delight. With cameo-like support ably provided by the charismatic Stanley Tucci and the bass-voiced Isaac Hayes, this movie emphatically revels in its premise that decent people can not only exist, but prosper, in a notoriously cold and bitter city, making It Could Happen to You an improbable but very agreeable modern day fairy tale, in which the good triumph, the wicked are punished, and wealthy young women just love being waitresses.

Down with Love5. Down With Love (2003)
Written by Eve Ahlert and Dennis Drake
Directed by Peyton Reid

I’ll just say it. I am a HUGE Doris Day fan. Her movies, along with those of my equally beloved Shirley Temple, were mainstays of my childhood, and even though the often salacious subject matter flew right over my head (I didn’t really get all the subtext in Pillow Talk until I was well into high school), I found the movies that showcased her as a modern, independent woman of an earlier era to be utterly captivating. Which is why I was trepidatious about assaying Down With Love, the 2003 homage to her works and starring Renee Zellweger in the Doris role. Also featuring Ewan McGregor as the confident and sexist man-about-town who once would have been played by Rock Hudson, David Hyde Pierce as the ambiguously gay Tony Randall-type, and a fun cameo from Randall himself, the movie gives us feminist self-help writer Barbara Novak (Zellweger) alongside the intrepid Catcher Block (McGregor) who is determined to undermine her message of female empowerment through chocolate. Under the bright lights of early-60’s New York, the two tussle, tangle, and tease until love ultimately wins out… and then they sing! Oh, what fun! Truly a worthy tribute to the great Ms. Day, and a movie for anyone who ever loved those Technicolor screwball comedies.

You’ve Got Mail4. You’ve Got Mail (1998)
Written by Nora Ephron and Delia Ephron
Directed by Nora Ephron

There is a moment at the end of this movie, when our contentiously courting couple Joe (Tom Hanks) and Kathleen (Meg Ryan) finally get together, and you can’t help but think: “Really? She can forgive him so easily? Really?” After everything that has transpired, it is quite a lot to swallow. Yet our leads are both so charming, and their torturous path to love so clever and funny, that you just let it go, let them have their moment, and try not to allow thoughts of their next fifty years of arguments culminating in “You closed down my mother’s store!” enter your head. (Or maybe that’s just me.) While at times this can seem like one long AOL ad, and to today’s wi-fi having crowd that irksome dial-up modem noise is both archaic and annoying, the Ephrons’ entertaining script and the well-established chemistry between Hanks and Ryan make up for much; add in Steve Zahn, perennial Other Guy Greg Kinnear (seriously, has he ever gotten the girl?) and an out-of-character but awesome appearance by comedian Dave Chapelle, and this story of two anonymous e-mail correspondents and their real-life antagonism is one that never fails to please.

Keeping the Faith3. Keeping the Faith (2000)
Written by Stuart Blumberg
Directed by Edward Norton

“The true New Yorker secretly believes that people living anywhere else have to be, in some sense, kidding.” So quotes Catholic priest Brian (Edward Norton, in his directorial debut) to his newly returned childhood friend Anna (Jenna Elfman), as he quietly develops a crush on her. Driven and career-orientated, Anna has also rekindled her friendship with Brian’s best bud Jake (Ben Stiller), a rabbi who is expected to marry a nice Jewish girl and settle down in order to get a promotion at his hidebound synagogue. When Jake and Anna commence a secret dalliance, neither expects it to go anywhere, but as the one-liners zing and the rules are defied, this unusual love triangle reaches a most satisfactory conclusion; also containing a message of religious tolerance (and about excessive cell phone usage), this film is by turns hilarious and poignant, and showcases the melting pot that is New York City at its finest. Norton and Stiller shine.

Moonstruck2. Moonstruck (1987)
Written by John Patrick Shanley
Directed by Norman Jewison

It is not often that “romantic comedy” and “Oscar-winning” can be put into the same sentence, especially not during cinema’s modern era. (Unless it stars Jack Nicholson, or is directed by Woody Allen.) But Moonstruck is one of those rare films that is romantic and a comedy and is considered worthy of acclaim, with six Academy Award nominations, three wins, and a whole lot of critic-y love sent its way. The movie tells of the widowed Loretta (Cher), approaching forty and about to settle into a loveless marriage, who meets her fiancé’s much younger brother Ronny (Nicholas Cage) and is eventually won over by his heedless, single-minded pursuit. Along the way there is much in here about the nature of attraction and fidelity and about society’s demands, as well as a whole lot of laughs, but at its core, Moonstruck is about two lost souls who find each other in that unlikeliest of rom-com locales: Brooklyn.

When Harry Met Sally1. When Harry Met Sally (1989)
Written by Nora Ephron
Directed by Rob Reiner

There is nothing about this movie that is not iconic. From the argument that men and women can’t be friends, to the “I’ll have what she’s having” restaurant scene, to the New Year’s Eve epiphany leading to a happily ever after, When Harry Met Sally is the pinnacle of chick flickery, and the first romantic comedy as we know it today. Its soundtrack replete with Harry Connick Jr. genius; a terrific supporting cast including Carrie Fisher and Bruno Kirby; Nora Ephron’s signature sparkling dialogue (for which, incidentally, she received an Oscar nomination); and New York City in all its splendid, seasonal variety puts this friends-to-lovers masterpiece among the most rewatchable movies ever made—where it joins another Reiner production, The Princess Bride. The credit for much of this must naturally go to its two appealing leads, Meg Ryan and Billy Crystal, who manage to make the objectively objectionable Sally and Harry both likeable and fascinating, and their slow-burn love story, for each other and their adopted city, both exhilarating and inevitable. Sure, any one of these other movies could have been awarded the top spot, but when it came right down to it… it had to be them.

N.B. In case you’re wondering at their omission, I have placed out of contention here three classic romantic comedy films, namely the original versions of An Affair to Remember and Sabrina (let us ignore the remakes entirely), along with Breakfast at Tiffany’s. The first I am ruling out because a lot of the important stuff takes place away from New York—ditto Annie Hall, and the more recent Going the Distance—the second because the May-December (nay, February-December) romance of Audrey and Bogart has always kind of creeped me out, and the third because of the racism inherent in Mickey Rooney’s Chinese landlord character, which renders large portions that much-adored film just…wrong.


Rachel Hyland is Editor in Chief of Geek Speak Magazine.

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1. bungluna
There must be something wrong with me. Of all the films you've mentiones, I've watched 6, liked 3 and been bored to tears by the others and only would consider re-watching 1. What does that say about a gal who will watch any "Die Hard XV" film anytime and who considers "The Blues Brothers" the greatest comedy ever but who can't stand rom-coms in general?

I do admit that "Two Weeks Notice" was uterly adorable.
2. JulieYMandKAC
When Harry Met Sally is for sure the #1 best! Great list!
Heather Waters
3. HeatherWaters
How to Lose a Guy in 10 Days didn't make the list! I've always enjoyed that movie, though it is pretty much 100% fluff.

Anyway, fun list! I adore Two Weeks Notice and It Could Happen to You.
Megan Frampton
4. MFrampton
I've never seen Two Weeks Notice, and now I want to. Thanks, Rachel!
Myretta Robens
5. Myretta
I'd move Moonstruck to #1. I found Billy Crystal and Meg Ryan just annoying in When Harry Met Sally.

And I must admit that Music and Lyrics, with Hugh Grant and Drew Barrymore, is one of my guilty pleasures. Right up there with Two Weeks Notice.

And, hey! What about Crossing Delancy? Teriffic movie.
Rachel Hyland
6. RachelHyland
@ 1. bungluna

As the EiC of a magazine entitled Geek Speak, and yet a chick, believe me when I tell you that I completely understand. These may be my Top 10 NY-Based Romantic Comedies, but none of them even approaches my personal Top 10 Movies of All Time. (Which is, however, topped by The Princess Bride. The Blues Brothers is on there, too.)

@ 3. redline_

How to Lose a Guy in 10 Days lost me somewhere around the poker game, and just never won me back. By the end of it, not only did I not care if Kate Hudson and Matthew McConaughey got together, I actively hoped they wouldn't. Watched it twice just to make sure I really hated it. And... yep.

@ Myretta

Music and Lyrics! I actually very much love Music and Lyrics, but in the final cut it lost out to Down With Love's homagey goodness. Mainly because I have a problem with the palpable lack of chemistry between the two leads. To me, the dynamic feels more favorite-uncle/spoiled-niece than anything. Gotta love that song he wrote for her, though!

I'll admit I forgot about Crossing Delancy -- which is probably why I wouldn't have included it on this list. Also, not sure I'd call it a rom-com. I didn't find it all that funny, but rather depressing, actually.
Louise Partain
7. Louise321
What happened to Kate and Leopold? and well if 42nd st didn't make it I guess Enchanted wouldn't either even though most of the action does take place in NYC.
8. Misseli
You left out one of my favourite modern New York romantic comedies: The Night We Never Met, with Matthew Broderick and Annabella Sciorra. A charming paean to New York, and its denizens.
Rachel Hyland
9. RachelHyland
@ 7. Louise321

Kate and Leopold certainly gets points for Hugh Jackman in breeches, but loses them for a) Meg Ryan's ridiculous pillow lips and b) for the bustle that somehow magically appears on her dress when she goes back in time. I 'm sorry, but exactly how does even the most plot devicey of time travel wormholes manage to adjust your wardrobe so that it's era-appropriate? Insanity.

@ 8. Misseli

You know, I have never seen that one -- and here I thought I'd seen all the romantic comedies ever. Thanks for the tip!
10. Vivi
How about Serendipity with John Cusack and Kate Beckinsale?
11. Laura T.
So when you say "the original version" of An Affair to Remember, I'm guessing you're talking about the wonderful version starring Cary Grant and Deborah Karr from 1957. Just as an aside (I'm a classic movie lover former VHS store employee) that version is ALSO a remake, as the original, original version is 1939's Love Affair starring Irene Dunne and Charles Boyer. Now, 1939 is a year where some of the best and most enduring films came out of Hollywood, and I adore Ms Dunne and Mr Boyer, but I recommend sticking to Grant and Karr's version. I'll recommend much better Dunne and Boyer films (though not together, I think....). OTOH, Love Affair was a blockbuster and a massive bofffo hit at the time. (I am just more charmed by Grant and Kerr in this case.)

Irene Dunne, I recommend The Awful Truth (1937), which is hysterical and funny enough, is oposite Cary Grant. ;-)

For Charles Boyer I recommend 1944's Gaslight. Which really isn't fair, because he plays a.....rear end of a donkey, but it's such a charming rear end of a donkey! Nor is Gaslight a rom-com (or comedy. or even romantic.) but the movie is in my top ten all-time favorites for Ingrid Bergman's last scene in the movie, which is a tour de force for her.

But how could you not mention two of the best romantic movies of all time (only one is a comedy, granted): 1946's Notorious and 1956's Indiscreet? Both star Cary Grant and Ingrid Bergman, and after watching both, I think you'll agree with me that it is a movie history crime that they only worked together the 2 times. Fun facts I toss out to get people to watch them: Notorious is the movie that got away with breaking the Hayes Code about kisses not going for longer than 5 seconds at a time, in a brilliant sequence. Indiscreet is the movie when Bergman's character says screams about Grant's character "How dare he make love to me and NOT be married !?!" A line I think you'll agree should be immortal.

Or what about Singing in the Rain? Or Bringing Up Baby? Or Monkey Business? (I could have a Cary Grant thing going tonight.....*g*)

Sorry for the long post; I tend to get long-winded about classic movies...
Rachel Hyland
12. RachelHyland
@ 10. Vivi

Serendipity also takes place outside of New York for major plot points (Kate Beckinsale lives on the West Coast, as I recall). Also... well, I don't exactly love that movie. I think it's the middle act; it just kind of drags, for me. Also, its insistence on the power of "destiny" drove me crazy. Cusack is in fine form in it, however...

@ 11. Laura T.

Hey, don't apologise for a long comment! Especially one that is that good.

True, the Irene Dunne Love Affair was the original, but it isn't nearly as iconic as the Kerr/Grant "original". And thanks for reminding me about The Awful Truth! It's one of those movies I caught the last forty-five minutes of on TCM one time, and always meant to track down so I could watch the whole thing. Will do so now!

I am actually a huge fan of old movies, especially old musicals, and adore Singin' in the Rain, Bringing Up Baby, Monkey Business, Notorious and Gaslight, but would argue that none actually fit the category. Singin' in the Rain is set in Hollywood, isn't it? Bringing Up Baby takes them out to Katharine Hepburn's family estate, doesn't it? I don't actually remember where Monkey Business is set, but since I don't recall its New Yorkiness, then I feel like it doesn't belong on a New York list. Neither Notorious or Indiscreet I would have considered rom-coms, but maybe that's just me.

They are all terrific movies, however, and certainly form the basis of another potential Top 10...
13. Richard Kenyada
One of my favorites is Frankie & Johnny (1991) with Al Pacino and Michelle Pfeiffer. The flower truck scene alone is worth the price of admission. Add a little Debussey's Claire deLune played against the canvas of New York City, and you've got romance with possibilities.
Shauna Comes
14. djshauns
I love You've Got Mail, and I have to agree that it always bothered me how easily it seemed that she was willing to get past him closing her store, but that is what happens when they try to update an old film and don't think too hard about how the big changes they make will really work in the storyline. The original Shop Around the Corner (1940) with Jimmy Stewart and Margaret Sullavan, and the older remake In the Good Old Summertime (1949) with Judy Garland and Van Johnson are both set in a single music store with the leads both being sales clerks in the store who don't get along and unknowingly become penpals. Once you place the two leads in competing businesses, you sort of have to ignore the fact that his big box store causes her small store to close. I guess they wanted to make a commentary on how chain stores kill small local businesses at the same time they made a romantic comedy, which is kind of crazy, because I can totally see her winning every argument in their future by bringing up the whole "you closed my mother's store" thing. It was kind of like the script writer thought, "Oh wait, we're an hour and a half into the movie, guess it's time to wrap things up and get them together," and you just have to ignore the fact that there is probably nobody that forgiving that they would just get past things that quickly, even if there was probably very little he could have done about the store moving into the neighborhood at that point (since when the movie opens, the "Fox Books" is already turning that building nearby into a new store).
Rachel Hyland
16. RachelHyland
@ djshauns

You've Got Mail was on TV a couple of weeks ago (when is it not?) and I got sucked into watching it yet again. What really made me grin was the idea that if they were to make a You've Got Mail 2, set today and featuring the next generation -- maybe the exploits of the precocious Matt and Annabelle? -- it would be "Big Bad Fox Books" under threat, mostly from e-commerce and e-readers. How quickly things change!

I have seen Shop Around the Corner, but had no idea about In the Good Old Summertime, and I love Judy Garland! Will be on the lookout. (Is it set in Austria, or whatever, like the Jimmy Stewart version? I remember that always really puzzled me...)
Shauna Comes
22. djshauns

I know what you mean about You've Got Mail. Of course, I am crazy enough that I actually bought it. As for Shop Around the Corner and In the Good Old Summertime, they were both on around Christmas one year for some reason, and I DVR'd both of them and have saved them on the list until I get a chance to track them down on DVD.

They actually changed the setting from 1930s Budapest to Chicago at the turn of the century for In the Good Old Summertime. No idea why the time change was necessary in addition to the location (I understand moving the setting to an American city, since the Budapest locale is kind of odd).
23. Diane Catherine
Thanks for this interesting and helpful list! I was thinking to myself, "I'm really in the mood for a romantic comedy set in New York." Google brought me right here, and I have only seen two of these (I don't see many movies), so with the list and the comments, I'm all set.

In the last paragraph, you used the term "lovers-of-friends," which puzzled me. Then I thought maybe it's just a typo and you meant "lovers-or-friends." Right? But overall, your writing is great! And when I got to the comments and saw "Myretta," I realized this must be a hangout for some of the names I used to see as a citizen of the Republic of Pemberley. =) Haven't been there in ages...should go see how they're doing!
Heather Waters
24. HeatherWaters
@Diane Catherine -- H&H mod here. How cool that you found us and that the list helped. I think you're right about that typo, it's probably either friends-to-lovers or lovers-or-friends--editor fail there, so I'll make the correction. :)

And yes, Myretta Robens also blogs for H&H! Hope you guys get to chat soon. Welcome!
Rachel Hyland
25. RachelHyland
@ Diane Catherine

Thank you for the compliments, and I'm glad you found the list helpful!

Re: "lovers-of-friends" -- I definitely meant that exactly as worded. It is a reference to the Frank Sinatra song "I Could Write a Book" where the line goes "And the world discovers how my book ends, how to make two lovers of friends." The fact that the song is covered by Harry Connick. Jr. on the When Harry Met Sally soundtrack, and features pretty prominently in the movie, just made it more apt to my (admittedly often addled) mind. Hope that clears it up! Although obviously, if a passing reference needs this much explanation, it may be a little, er, obscure. I'll watch out for that in future...

@ redline_

As if the editors of H&H ever fail!
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