The Best NYC-Based Romantic Comedies, From 2000 To 2005

We have just made the transition into Rom Com Season, where you'll probably, at least once, find yourself under a blanket on a Saturday night, encircled by empty bottles of red and crying a little as fake, unrealistic love mocks your lonely life from a television screen. Or perhaps you're bundled up with your eau de pine scented Winter Boyfriend, forcing him to sit through saccharine storylines soundtracked by Train after a day of shopping at Anthropologie. Either way, 'tis the season, and you know what goes great with Romantic Comedies? New York City.

Below, a list of the best rom coms that have taken place in NYC between the years 2000 and 2005—we'll get to other years at a later date, but we're starting here because these five years produced some of the best-worst and best-best rom coms. We're not talking about your precious indie mumblecore rom comishdies, you won't even see The Baxter on this list (that excellent little film is just too good)—here we're talking about The Big Hollywood Rom Com. The one with the A-listers, the one defined as "a funny movie about a love story that [SPOILER ALERT] ends happily."

KEEPING THE FAITH (2000)

If someone told you a rom com starring Ben Stiller, Edward Norton, and Jenna Elfman was coming out it would seem almost unbelievable now, but it happened 14 years ago. Centered around a love triangle between three childhood friends (now adults: a rabbi, a priest, and a Very Important Business Lady), the movie features a nice chunk of NYC as well. And the characters are big fans of their city, Norton's Father Brian Finn says, “The true New Yorker secretly believes that people living anywhere else have to be, in some sense, kidding.” This was also the actor's directorial debut.

DOWN TO YOU (2000)

Julia Stiles co-stars alongside Freddie Prinze, Jr., and while she shined as the angsty, Bell Jar-reading rebel teen in 10 Things I Hate About You, she's always been an awkward fit for a traditional rom com role like this one. But her awkward fit and Freddie Prinze, Jr.'s bad acting are all made up for by a terrific supporting cast: Rosario Dawson, Lucie Arnaz, Henry Winkler, Zak Orth, and Ashton Kutcher (I know I know but... Ashton as Jim Morrison in this movie is his best role!).

KATE & LEOPOLD (2001)

"Kate [played by Rom Com Queen Meg Ryan] and her actor brother live in NYC in the 21st Century. Her ex-boyfriend, Stuart, lives above her apartment. Stuart finds a space near the Brooklyn Bridge where there is a gap in time. He goes back to the 19th Century and Leopold—a man living in the 1870s—follows him back through the gap into present day." WHY AREN'T YOU PRESSING PLAY YET? Seriously, it's like a harlequin romance novel for history buffs come to life.

SERENDIPITY (2001)

Ben Yakas, who never shuts up about Serendipity and we suspect teaches a night class about it at Columbia, has this to say about the film: When you talk about Serendipity, you have to talk about "Mystic Surrender," the brilliant Shehnai music video from the legendary Lars Hammond (a never more brilliant John Corbett). It is both the best thing about the film ("The problem is you can't fend off an army of blood thirsty Vikings with a Shehnai, it's illogical") AND a kind of keystone for understanding this movie's warped view of "fate" and "romance" and "stalking." Here is the secret to love according to this film:

a) Spend a single evening with a frustrating person who thinks writing their number on five dollar bills and defacing books is charming
b) Because coincidence=love (This movie has a lot of trouble distinguishing between coincidence and fate)
c) But! You have to actively not try to find that person by conventional means for SEVERAL years afterwards, because that would be cheating or something
d) Staying in dead relationships is cool—actually, getting engaged to a partner you aren't in love with is cool too
e) Shit will just work itself out!

Addendums:

-This film is really special in that it has indie synergy with the namesake restaurant—would people (re: movie executives, audiences, dessert fans) think it was just as romantic if this movie were called Applebees, or if the couple shared a bloomin' onion at Outback Steakhouse?
-The (first) Macguffin in this film is a set of black cashmere gloves. They both keep only one, ensuring that neither they nor their much-ignored partners have a full set. Who are these selfish idiots?
-The romantic leads of this film only spend about 15-20 min onscreen together, at the very beginning and the very end. This is because they would likely hate each other if they spent as much time with them as we were forced to.
-This movie is very important for Jeremy Piven Hair Truthers

MAID IN MANHATTAN (2002)

As far as mistaken identity rom coms go, this one is pretty good. It's got Jennifer Lopez playing a single mom and maid in a posh Manhattan hotel, and her love interest Ralph Fiennes as good guy senatorial candidate Christopher Marshall. Toss a whip-smart kid into the mix, who knows juuuuuust when to tug at your heartstrings, and you've got rom com gold. Bonus: you'll also get Chris Eigeman, Stanley Tucci, and the late great Natasha Richardson.

TWO WEEKS NOTICE (2002)

This one features the one time Prince of Rom Coms, Hugh Grant, and the clumsy Princess of the genre, Sandra Bullock. The IMDB summary reads: "A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him." But that is hardly an apt description of this fine film, which has Grant playing some modern day Robert Moses... or maybe it's Donald Trump. As for Bullock, she's a Jane Jacobs-influenced lawyer who ends up working for Grant's character. Will love blossom in the most unlikely of pla... of course it will, this is a rom com. Bonus: you'll learn a little bit about the history of the Chrysler Building.

DOWN WITH LOVE (2003)

You won't really get any recognizable version of New York City here, but the story does take place in an early 1960s Manhattan, and the movie itself is somewhat a parody of the romance movies from that time. Renée Zellweger plays Barbara Novak, author of a best-selling book that guides women away from the altar and towards sex “à la carte," and her nemesis is played by a dashing Ewan McGregor, an investigative reporter and ladies man about town. The New Yorker called it: "a wondrously neoclassical comedy... directed with exquisitely controlled whimsy by Peyton Reed."

HOW TO LOSE A GUY IN 10 DAYS (2003)

As with most rom coms, you'll need to suspend disbelief a bit while watching this plot line play out, but it's more enjoyably stupid than it is cringe-worthy. Kate Hudson plays Andie Anderson, a glossy magazine writer with dreams of doing Important Journalism. Her target for a new How To column is Matthew McConaughey, playing ad exec Benjamin Barry. Don't want to spoil how this one ends, but they go to Staten Island and yadda yadda yadda that backless yellow dress, champagne, drunk meltdown, TRUE LOVE.

13 GOING ON 30 (2004)

Every girl had some version of this dream, right?: Skip the awkward early teen years and wake up at 30 years old as a "big time magazine editor" in New York City, with a dream apartment, a best friend you're in love with, and not an ounce of jadedness that your twenties would have instilled in you. This movie has got all of that, plus rom-com staple co-star Judy Greer. It's all so perfect... until, of course, they (spoiler alert) decide to move back to Jersey in the end.

ALONG CAME POLLY (2004)

This movie is one of the best rom coms of the early 'aughts because of Philip Seymour Hoffman. The end.

HITCH (2005)

Hands down the best rom com we saw in the early aughts, and isn't New York City history so romantic? It pops up on a first date in this one, in a tear-jerky scene that is fantastic until things go very wrong... as they always briefly do in rom coms. As Hitch fan Aziz Ansari once declared, "Aren't we all just Albert Brennemans trying to find our Allegra Cole? The story of Hitch is timeless."

LITTLE MANHATTAN (2005)

Rebecca Fishbein has a lot of feelings about this one, here's what she has to say about it: It's not often that a rom com meet-cute takes place in a Tiger Schulmann karate class. But that's where Little Manhattan protagonist Gabe (a pre-Hunger Games, pre-pubescent Josh Hutcherson) first realizes that fellow tween Rosemary Telesco (Charlie Ray) isn't just some cootie-covered girl, and falls madly, deeply, in love, sixth grade be damned. This film is arguably the most adorable of all the city-centric rom-coms, following Gabe as he navigates his first, bittersweet love. Gabe's parents, heartbreakingly played by Cynthia Nixon and Bradley Whitford, are in the middle of a difficult divorce, but like many city couples, they're forced to live together in their Upper West Side apartment. Gabe's just old enough that he's given free reign over a slice of the city—from his apartment on 72nd and West End to the American Museum of Natural History—and he zips around within his boundaries on a scooter, offering viewers shots of Fairway Market and Central Park.

And of course, like any good rom-com, there are some conflicts here. Though Gabe and Rosemary both go to public school together, Rosemary's family is wealthy, and the threat of summer camp and private school threaten their future together, teaching Gabe that "Love is an ugly, terrible business practiced by fools. It'll trample your heart and leave you bleeding on the floor. And what does it really get you in the end? Nothing but a few incredible memories that you can't ever shake." Gabe is 11. This movie will slay you. Watch it immediately.

Honorable Mention to 2005's A Lot like Love, which is actually pretty fantastic but more rom dram than rom com. It also only briefly features NYC. Anyway, don't be scared off by Kutcher, watch it!