What’s New York City really like? I’m a film geek, so when I want to learn about a place, I turn to movies. But here’s the rub about New York City movies, the city seems like it has a personality disorder.

You have Martin Scorsese’s New York on the one hand and Woody Allen’s New York on the other. Then there’s Spike Lee’s New York juxtaposed with Nora Ephron’s New York.

It’s a city with many personalities: the sympathetic intern and her monster of a boss; the lizardly Wall Street yuppie; the deceptive Broadway star; the reclusive millionaire; the heroin junkie; the tempting blonde next door; the crippled voyeur; the hyper-masculine boxer; the psychotic mistress; the male model; the bitter ex-wife; the chosen one; the grim reaper; the struggling bartender; the dysfunctional patriarch; the giant ape; the photographer bit by a radioactive spider; the sex columnist; the white swan and the black swan.

New York City is portrayed as a dream and a nightmare. It’s a land of fantasies, sad realities, and pure, unfathomable evil. That’s New York, baby!

In honor of the many faces of New York, I’ve compiled a list of my favorite New York City movies and their unique New York personalities.

Please Note: I limited my list to one film per director.

Favorite New York City Movies

10. Big Daddy (1999)

There’s not much you should like about Sonny Koufax (Adam Sandler). He’s a graduated law student who never took the bar. He lives off an investment that resulted from a minor taxi cab accident. He’s lazy, irresponsible, and over privileged. For Sonny, New York is a playground, a place where you waste time throwing sticks in front of roller-bladers. More infuriating still, he lives in Manhattan, in a great apartment that he shares with Jon Stewart. Does it get any better?

His apartment is his playpen. However, his careless lifestyle’s altered when he impulsively adopts a child to show his girlfriend that he can commit. Is Big Daddy a cinematic masterpiece? No. It’s a rip-off of Charlie Chaplin’s silent classic The Kid (1921). But Adam Sandler’s New York is still a fun escape. Sometimes, for a city that seems to take itself far too seriously, that can be refreshing. In my opinion, Big Daddy is Adam Sandler’s last great comedy. Like Billy Madison (1995) and Happy Gilmore (1996), Sandler and his supporting cast bring the film to life and keep you laughing throughout. What I look for most in a good comedy is the number of lines I deem quote-worthy. After more than a decade, I still quote Big Daddy (and significantly more during football season, when the Patriots are playing the “goddamn Jets.”)

9. American Psycho (2000)

American Psycho is the ear worm of movies. Once it enters your mind, it refuses to vacate, slowly slinking its way past your ear drum to your inner mind, where it gnaws at the essential, meaty parts of your psyche. It haunts you when you hear a Huey Lewis and The News song. You shiver every time you see a business card. And then there’s Christian Bale. Patrick Bateman was his breakout character. Fourteen years later, he’s still Patrick Bateman; even as Batman (which adds an interesting dimension).

Based on the novel of the same name by Brett Easton Ellis, American Psycho paints a picture of New York in the 1980s, at the height of the yuppie reign. Unlike Wall Street (1987), American Psycho exposes what the pressures of working in New York can do to a person’s mind. In Bateman’s case, it spawns a psychotic alter ego. American Psycho skillfully paints a picture of New York as a superficial nightmare, and although the era has changed, the pressures of New York have not. These pressures will always blow through the New York air, which leaves the potential for you to become another Patrick Bateman.

8.  As Good as it Gets (1997)

New York is a filthy city. It’s known and famous for its filth. All of those citizens produce germs. That’s a terrifying thought for someone that’s OCD.

For Melvin Udall (Jack Nicholson), New York’s a nightmare, but it’s also the only imaginable place to live. Melvin’s entire routine is constructed around that dirty city. Of course, Melvin’s routine is shot to hell when his homosexual neighbor, Simon (Greg Kinnear), is attacked and Melvin’s forced to care for his germy pup. (Melvin’s also homophobic.)

While As Good as it Gets celebrates the Hollywood cliché that love cures all, it also gives you a glimpse of the artist’s New York. It shows the love/hate relationship that artists have with the city. It’s the best and worst place in the entire world.

The real reason to watch the film, though, is for the performances. Both Nicholson and Helen Hunt won Oscars for their performances, and I’d argue that Nicholson’s performance is the best performance by an American actor in a leading role. (His biggest competition: himself as Randall Patrick McMurphy in One Flew Over the Cuckoo’s Nest [1975].)

7. Rosemary’s Baby (1968)

Speaking of nightmares, welcome to Roman Polanski’s vision of New York. While American Psycho tickles the psyche of an over-pressured brain, Rosemary’s Baby asks, “How far would you go for your dream career? Would you sell your soul for it?”

This classic film follows a young couple who relocates to New York, specifically The Bramford building (really the historical Dakota, where John Lennon was later shot). Rosemary (Mia Farrow) soon discovers the other tenants are part of a demonic cult. But that sounds crazy, right?

Polanski shows New York as a beautiful city filled with temptations. It’s a city that feeds off of innocent souls. Rosemary’s Baby was mind rattling for its times and an early introduction into “New Hollywood,” which governed in the 1970s. The film not only frightened audiences on the surface, but it was also a reaction of the fright felt by men due to the women’s rights movements of the time. Still today, Polanski’s classic remains timeless. It still holds the power to frighten audiences and its purpose still holds cultural relevance; so relevant that NBC has created a new miniseries.

6. On the Waterfront (1954)

Where would New York be without its working class heroes? Their story often goes unsung. They’re shadowed by the glitz and glam and suits and ties often associated with New York. But that’s not the New York that Elia Kazan knew. As an immigrant who arrived on the New York waters at a young age, that’s where Kazan saw the heart of the city. That’s where he found his New York: on the waterfront.

Kazan doesn’t expose New York as either a dream or a nightmare. He shows the working class’s struggles and the corruption they face. Kazan’s New York is neither black nor white: only an array of grays.

On the Waterfront follows Terry Malloy (Marlon Brando), the could’ve-been-contender who’s mixed in with the mob that controls the unions. Terry soon meets his ideal, virginal girl (Eva Marie Saint) and gains a conscience.

During the late 1940s and early 1950s, corrupt unions in the New York Harbor was a reality. It was the headlines that inspired Kazan’s masterpiece. The film was a testament to union corruption of the times, but it was also a personal testament by Kazan about how sometimes “ratting” is the right thing to do. He used this film as a platform to address his participation as a “friendly witness” in the HUAC hearings.

5. Vanilla Sky (2001)

Continuing the theme of New York as a dream or nightmare, Cameron Crowe shows the city as both, literally, in his remake of the surreal Spanish film Abre Los Ojos (1997).

Vanilla Sky revolves around David Aames (Tom Cruise), a Manhattan publishing heir who refuses to take life seriously. His life changes when he meets the beautiful Sofia (Penelope Cruz). Like a folk song, one night with Sofia inspires David to become a better man. Unfortunately, David’s careless past catches up with him and leads to a fatal accident, leaving the once handsome and charming man broken and disfigured. From there, his life spirals so far out of control that you’re left wondering what’s real and what isn’t?

Cameron Crowe’s New York wears a mask, hiding its true nature. His New York is beautiful and heartbreaking; it’s a Monet painting and Dante’s hell. Crowe’s New York is an absolute freedom and inescapable confinement. His New York is a Bob Dylan album cover. It’s as surreal as an empty Times Square. Cameron Crowe’s New York is like a folk song, it’s both bitter and sweet.

4. Taxi Driver (1976)

When I think of New York, four words come to mind: “You talkin’ to me?”

Travis Bickle (Robert DeNiro) is the classic anti-hero. He’s a Vietnam Vet (who clearly suffers from some form of PTSD). While cruising the downtown streets in his yellow cab, Bickle is bitter and disgusted over the human behavior in New York. He has little faith in his government, so he takes the law into his own hands, vowing to rid the city of its filth. But here’s the thing about Travis Bickle that a lot of people miss: he’s completely nuts. Yet, everyone roots for him. Isn’t that a nightmare in itself? Of course, that’s all part of Scorsese’s mastery. For Scorsese, the “Devil comes with a smile.” He likes to screw with his viewers. He cons viewers into rooting for the bad guys.

In Taxi Driver, Scorsese also focuses on the nightmarish truths of American reality. New York crime was at an all-time high in the 1970s. Across America, returning Vietnam vets who’d just survived real nightmare experiences, weren’t receiving the treatment or respect they needed and deserved from the American government. Americans had been lied to about the war and soon after, the Watergate Scandal. The country was amid the greatest economic crisis since The Great Depression. America was discontent and the government was the villain. For some, the insane Travis Bickle seemed like a better role model than the government. That’s saying something, isn’t it? Two years after the birth of Bickle, Superman (1978) soared onto the screen and rescued New York. In 2014, at the height of comic book movies, you’ll see, we’re still rooting for vigilantes like Bickle.

3. Manhattan (1979)

Woody Allen’s New York isn’t a dream, but he’s upfront that it’s romanticized.

Manhattan follows what every non-New Yorker imagines as the stereotypical New Yorker. Isaac (Woody Allen) is a divorced T.V. writer whose ex-wife left him for a woman. She’s now writing a book about their marriage. Issac’s a Jewish, left-wing intellectual. He’s dating a girl a little too young for him (and later falls in love with his best friend’s mistress). He’s self-deprecating and relies on his “analyst” to keep his messy life together.

Isaac is the neurotic New Yorker. Like most Allen films, this is a personal film, centered on a small, intimate group of people. There’s not much glam. Manhattan is only suggesting that, while these petty problems exist all across America, they’d rather deal with them in New York. The film’s black and white, offering a classic Hollywood feel like a good romance (this one with the city), but with the film’s 1979 release (at the height of the New Hollywood collapse), it also feels like a love letter to great cinema.

2. The Godfather (1972)

Is an explanation really needed? It’s kind of the best. And yes, I’ll say it: Part I is better than Part II. Part I has something Part II doesn’t: Brando.

The Godfather follows an immigrant patriarch, Don Vito Corleone (Marlon Brando), and his powerful mob family. Don Vito Corleone is a man who’s worked hard for what he has. He’s living his version of the American Dream. But the film’s not just about him. It’s about his family, their tradition, their legacies, dynasties, and death . . . lots of death.

Is The Godfather sexist? Of course, but so was America in the 1970s (*cough* and today). That’s what The Godfather does: expose the world for what it is. It’s sexist, violent, and corrupt. What better backdrop to display these themes than America’s culture capital?

Sure, the Corleone family has relocated to the burbs of Long Island, but Francis Ford Coppola saves the violence and the transformation into darkness for inside the city limits. Coppola’s New York isn’t a romance or fairytale. It’s about a man who achieved the American Dream, which makes it far more frightening than any nightmare.

1. Breakfast at Tiffany’s (1961)

Is there anyone more “New York” than Holly Golightly? She’s the icon. Other than the Statue of Liberty, she’s the lady of New York. Her look says it all: classy; fashionable; dark; beautiful; exposed, but hidden. Like New York, Holly’s the height of class, but also a call girl.

Breakfast at Tiffany’s, which is based on Truman Capote’s novella, follows New York socialite Holly Golightly (Audrey Hepburn). She seems like your typical fairy tale heroine, but she’s no princess, even as glamorous as she seems. She’s a tortured soul, always looking in, but never really being in. Holly’s haunted by her past and the person she once was. Her greatest fear is falling in love. Holly’s a timeless figure who transcends generations, stylistically and emotionally. She’s a little piece of every woman.

Is Holly a prostitute? She might be, but she might not. Her lifestyle suggests it. Then again, the mere suggestion is indication of the end of an era – the production code era of classical Hollywood. Paramount Pictures showed some big kahuna’s in casting America’s golden girl as a could be prostitute. Sure, the film has its flaws, like an incredibly inappropriate performance by Mickey Rooney, but you don’t watch Breakfast at Tiffany’s for him. You watch it for Audrey Hepburn. After all, it’s the role that made her a Hollywood icon. And she’s the prettiest face of New York.

Now that I’ve shared my favorites, what are yours?

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