1. How to Marry a Millionaire (Negulesco, 1953)
If you don’t want to watch classic cuties Marilyn Monroe, Betty Grable, and Lauren Bacall run around NYC trying to steal the hearts (and wallets) of the most wealthy bachelors in town, well, this film isn’t for you. But who wouldn’t want to. Honestly.
2. Breakfast at Tiffany’s (Edwards, 1961)
This list would be incomplete without mention of Miss. Holly Golightly played by the always classy Audrey Hepburn in Breakfast at Tiffany’s. Not only did it win two academy awards but it was also selected to be preserved in the National Film Registry in 2012. So you know it’s good.
3. The French Connection (Friedkin, 1971)
This adaptation of the non-fiction book of the same name starring Gene Hackman, Fernando Rey, and Roy Scheider was the first R-rated film to win the Academy Award for Best Picture and it’s full of drugs, detectives, and intense chase scenes. Well, mostly just the one, but it’s one of the best car chases in movie history.
4. The Godfather (Coppola, 1972)
Hopefully you’ve seen Francis Ford Coppola’s crime film masterpiece The Godfather, but if not, all the more reason to run off and do so right now. Not only is it packed full of some of the most iconic quotes from movie history, but the American Film Institute has ranked it as the second greatest film in American cinema. Now go have a movie night with Don Corleone.
5. The Way We Were (Pollack, 1973)
If you’re looking for a meandering, rather somber, non-love love story, this is the film you want. Starring Robert Redford (always a plus) and Barbara Streisand (another plus), their relationship is re-told partially in flashback, and even if you aren’t interested in the story, the costumes and sets more than make up for it (but the story is lovely).
6. Taxi Driver (Scorsese, 1976)
This dark crime/vigilante film follows lonely, ex-marine Travis Bickle (played by a young Robert De Niro) who becomes a nighttime Taxi Driver in NYC to cope with his chronic insomnia. The film is widely regarded as one of the greatest American films of all time, and while it deals with dark ideas, it’s hard not to be amused by Travis’ quirky personality and love exploits.
7. Annie Hall (Allen, 1977)
Woody Allen is known for his films in and about NYC, but Annie Hall is usually considered his most critically acclaimed film, particularly because it won the Academy Award for Best Picture. Allen, the director and lead actor, is known for his eccentric and often cynical dialogues about life, love, and relationships. Just another film about relationships—but an exceptionally funny one.
8. Tootsie (Pollack, 1982)
Everyone wants to watch Dustin Hoffman play a woman. In fact, Hoffman said about the role, “There’s too many interesting women I have…not had the experience to know in this life because I have been brainwashed [by cultural beauty standards]” and playing a female character led him to those realizations. So in addition to this film being comedy gold and a cute love story, it’s also forward moving for women. And there are of course some great NYC street shots.
9. Coming to America (Landis, 1988)
This comedy film starring Eddie Murphy, while not necessarily critically acclaimed, was well received by the public and if you’re looking for a memorable 80s comedy, especially one with great costuming, definitely give this one a try. Sure, it’s a little silly, but sometimes you’re just in the mood to watch a movie about a prince from a fictional nation coming to America for the first time.
10. When Harry Met Sally (Reiner, 1989)
The film that brought up the question “can men and women ever be just friends?,” When Harry Met Sally is a dialogue based movie exploring sex, relationships, and how men and women interact. Meg Ryan and Billy Crystal are hilarious and It’s full of beautiful shots of NYC plus a soundtrack by the smooth Harry Connick Jr.
11. Goodfellas (Scorsese, 1990)
Another film adapted from a non-fiction novel, Goodfellas is the movie you want when you’re feeling a swanky crime/drama, a particularly violent one, of course. Joe Pesci who played Tommy DeVito won the Academy Award for Best Actor in a Supporting Role, and for good reason as his famous “funny like a clown” speech was improvised by the actor. And did I mention the soundtrack?
12. You’ve Got Mail (Ephron, 1998)
This film is an old story presented in a new way. Well, it was new in 1998. The technology may be a bit outdated, but Meg Ryan and Tom Hanks are so charming, and Nora Ephron has always had a way of making NYC magical in her movies. That sounds cliché, but it can’t be denied.
13. Cruel Intentions (Kumble, 1999)
Are you looking for remarkably independent, sassy, wealthy teens waltzing around the city, giving each other lessons in kissing, manipulating one another, and just causing general mayhem? This is what you need in your life. Sarah Michelle Gellar is beautifully conniving as the lead, and while the critics weren’t too fond of it, it has a bit of a cult following.
14. American Psycho (Harron, 2000)
Described as a cult psychological thriller black comedy film, American Psycho is exactly that. Be warned that it’s really not for the faint of heart. Patrick Bateman, played by Christian Bale, struts around the office during the day as an arrogant business man, and… also struts around after dark carrying out his murderous tendancies. I’d recommend the book, too. If you can handle it.
15. The Royal Tenenbaums (Anderson, 2001)
Wes Anderson is known for his distinctive visual and narrative style, and of course, this film is one of his best (honestly they’re all good, though). Watch this when you want something with a sort of ironic humor, a collection of peculiar characters, and really neat cinematography. And look out for Gene Hackman, who plays Royal Tenenbaum. He earned a Golden Globe for his performance.
16. Catch Me If You Can (Spielberg, 2002)
Yes, Leo, I’d love to. This film follows the real story of the life of Frank Abagnale Jr. (played by Leonardo DiCaprio) who impersonated a pilot, doctor, and prosecutor and was able to con millions of dollars for himself all before his nineteenth birthday. If that doesn’t sound thrilling to you, well, you should watch it anyway because not only are the sets and costuming glorious, but so is the acting, writing, and I mean, it’s Leo.
17. How to Lose a Guy in 10 Days (Petrie, 2003)
When comparing this film to some others on the list, you may find yourself asking… why is this here? Well, let me tell you: if you like rom-coms you will like this movie, and if you don’t like rom-coms, you’ll probably like it anyway. Kate Hudson and Matthew McConaughey are both hilarious and believable. This is a belly laughing movie, take my word for it if you’ve never seen it.
18. Eternal Sunshine of the Spotless Mind (Gondry, 2004)
Despite the fact that Jim Carrey often plays comedic roles, this film is an excellent example of a more dramatic character. The quirky drama-romance follows Joel Barish (Jim Carrey) and Clementine Kruczynski (Kate Winslet) through a non-linear account of their relationship after they have erased each other from their memories. It’s striking and odd and in New York so of course it made the list.
19. New York, I Love You (2008)
There’s no director listed for this film because there are eleven of them and they wouldn’t all fit! New York, I Love You is actually a collection of short films all from different directors, and all related to the topic of love. Each one was filmed in one of the five burroughs of NY, and they’re all quite different. You’ll have to check this one out on your own.
20. The Wolf of Wall Street (Scorsese, 2013)
Here we have Leo feeling defeated because he didn’t get an Oscar for this role (he did get a Golden Globe, though, so it’s a start?). If you haven’t seen this nearly three-hour epic story based on the memoir of former stockbroker, Jordan Belfort, you definitely should. Though as you’ve probably heard, it’s quite explicit in terms of drug/alcohol use and sex, so just be aware. Leonardo DiCaprio’s performance really is worth your time though.