You might rename this list the top ten romantic movies for men, but I have found that all of the films here have really transcended either gender and are simply great films, that just happen to be incredibly romantic.
#10 - Before Sunrise
The first time I saw this film, I was expecting something completely different. The film takes place within the space of 24 hours and revolves around a couple who've just met each other and have decided to spend the whole rest of day together (before he has to go back to America). They fall in love, or at least as close to 'in love' as is humanely possibly possible. And the amazing thing is: we buy it. Like virtually all of Richard Linklater's films, Before Sunrise focuses on plain, ordinary people and their interactions with each other. There is no real plot in the film, but the movie is driven almost exclusively in the development of these two characters.
#9 - Annie Hall
Perhaps the best of Woody Allen's work, Annie Hall is wonderfully witty film about a couple that spend years trying to court each other. Love is not always peddles and chocolates and we see each splendidly imperfect detail throughout the course of this movie. The film has a pace and a style unique to Allen's work. The script is as brilliantly executed. If you've never seen a Woody Allen film, start with this one.
#8 - The Apartment
The only director to have two movies land on this list, Billy Wilder's The Apartment is one of a kind. Jack Lemmon is in top form as C.C. Baxter, an aspiring businessman who looks to gain favor with his fellow executives and rise in the ranks by lending out his apartment as a sleazy sex pad. Things complicate however, as he develops a romance of his own. Every time I see this film, I just wonder why romantic movies today can't be so beautifully simple now.
#7 - Pride and Prejudice
It's hard the screw up perhaps the greatest romantic novel of all time. Joe Wright, who I believe to be one of the most under appreciated visionaries of our day does a brilliant job of adapting this classic into only two hours. The acting is spot on (despite what you may or may not think about Keira Knightley). The cinematography is gorgeous! While most women are likely to tell you that BBC's six hour, Collin Firth special is the greatest of its kind, in terms of shear storytelling, Joe Wright's version is superior.
#6 - Silver Linings Playbook
Certainly my favorite romantic comedy of the last decade, Silver Linings Playbook is the story of two chemically imbalanced misfits who are both trying to put their lives back together. What makes this film so delightfully charming is its brutally honest, 'accept me for who I am' mentality. While mental illness has become an increasingly acknowledged problem in out society, Silver Linings manages to give it an honest portrayal and yet still remain hopefully optimistic.
#5 - I Married a Witch
This is one I was tempted to put on the Halloween list a few weeks ago, but decided that it really belongs here amongst the hopeless romantics. While not as wildly popular or recognized as the Arsenic and Old Lace's of this world, I Married a Witch is just as funny and infinitely less known. This is the original Bewitched and now the standard for romantic comedies today.
#4 - Groundhog Day
Some might argue that this one is neither fish nor fowl. I believe this to be the most morally significant film on the list. A man is essential given all eternity to figure out himself and then woo the woman of his dreams. The movie is really about him and the change in him, but is just as sweet and romantic as any on the list. Bill Murray gives us one of his most memorable performances in what I consider to be his most important film.
#3 - Some Like It Hot
Before Mrs. Doubtfire, Tootsie or those awful Wayne brothers and Eddie Murphy movies (I'm sorry, bad example) there was Some Like It Hot. A brilliantly witty story about a couple of men that are willing to do just about anything to get with a woman (and not be killed by the mafia). The film is hilarious and smart in a way that films just don't seem to reach these days.
#2 - It Happened One Night
Of all the achievements of Frank Capra, this one is the only one that won him a Best Picture. It may be incredibly old fashion (as most all of Frank Capra's films are) but It Happened One Night is truly a gem. A savvy and cutthroat journalist strikes gold when he happens to catch a bus with a runaway heiress. She's a spoiled brat and he's a hard hearted pessimist. I loved every minute of this film.
#1 - When Harry Met Sally
Perhaps the greatest date movie of all time, When Harry Met Sally is what happens when the sexes decide to come together and talk about sex. Can Men and Women just be friends? I can't think of one thing I don't like about this movie. Meg Ryan is splendid. Billy Crystal is still Billy Crystal. And Rob Reiner brings us his golden child.
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