|10. Manhattan (1979) – With one of the best film introductions in history, a brilliant voiceover, and a beautiful usage of George Gershwin’s music ~ nothing gets much better than this little film… except for the following 9 films.Woody Allen stars as Isaac Davis, a TV comedy writer who dreams of being the next great American novelist. His second ex-wife, Meryl Streep, is a lesbian who wrote about their failed marriage. Allen’s best friend has an affair Diane Keaton, but before long the find themselves falling in love instead. Manhattan is a treatise on New York and New Yorkers.
|9. Sleepless in Seattle (1993) – The film is practically the bible on making modern romantic comedies.A radio talk show psychologist asks her audience what they are wishing for this holiday season, and Tom Hanks’ son asks for his father to find a new wife. Across the country Meg Ryan hears the wish and is captivated by it. Tom Hanks is inundated by letter from listeners reaching out to him. Ryan becomes convinced that it is her destiny to meet Hanks. Only issue is that Ryan is engaged and doesn’t know Hanks yet.
|8. Harold and Maude (1971) – The movie promise of the premise is fulfilled so incredibly that when it delivers on what love between young and old is you cannot help but feel it as well… which is very disconcerting.A 79-year-old high lady and young man with a death wish fall in love. Bud Cort tries to commit suicide in hilarious ways desperately looking to get his mother’s attention. Completely obsessed with death and dying he starts attending funerals where he meets Ruth Gordon. Ruth is a free spirit and does some nude modeling. Breaking every taboo and making relatives incredibly unhappy, Bud falls in love with Ruth. Ruth teaches Cort a real life lesson in truly living one’s life.
|7. Breakfast at Tiffany’s (1961) – Maybe I’m a sucker for New York love stories, maybe it’s because I have one, but somehow they seem the most honest.Audrey Hepburn is a charismatic socialite who lives alone, and won’t even give her cat a name because she’s so commitment-phobic. She spends her days at high-class parties, on expensive dates, and wearing the most chic garments. Hepburn’s carefree attitude is changed when she meets her neighbor, aspiring writer George Peppard who is living off of a much wealthier woman. Hepburn and Peppard are halfway to falling in love when a doctor reveals the truth about Hepburn’s past.
|6. Wall-E (2008) – Hilarious, poignant, barely any dialogue, and yet somehow completely connects on all levels emotionally ~ a real masterpiece.
Set in a post-apocalyptic world where humans have littered the earth into uselessness and evacuated the planet, Wall-E ~ an incredibly cute robot, is left to cleanup the refuse. When a female robot makes its way back to earth Wall-E suddenly experiences love. Lonely boy robot on dying planet meets girl robot and falls in love. He chases girl robot to the ends of the universe, and also manages to save humanity.
|5. Amélie (2001) – Visually it’s just unbelievable what Jean-Pierre Jeunet comes up with and is able to pull off. From talking statuettes to photos that come to life, and skipping rocks that go endlessly into the distance… it’s almost too poetic.
Audrey Tautou is a delicate French girl who loves to sort out her friend’s problems. When she suddenly gets a crush on someone she sends him riddles he must solve in order to meet and kiss her.
|4. Edward Scissorhands (1990) – Fun Fact: Before Depp was cast supposedly Tom Cruise, Tom Hanks, Robert Downey, Jr., and William Hurt, were all in contention for the role. This movie has one of my favorite bookends to a film where the old lady, Winona, remembers her love up there in the mansion who is still to this day creating landscape statues.Johnny Depp is an unfinished scientific experiment who has scissors for hands. A modern day Frankenstein, Johnny ventures down from his inventor’s mansion into Suburbia, and finds love with Winona Ryder. Things get rocky when Johnny comes up against some of the town’s antiquated views, and their problems heighten when Johnny realizes he will outlive his love.
|3. Before Sunrise (1994) – That sense of infatuation at chance meetings rings true here, and reminds me of all those days I spent abroad myself. Richard Linklater’s incredible ability to direct realistic and intriguing conversations is brought to light here. Fun Fact: He hung out for three long days with both protagonists and they wrote the screenplay together.Ethan Hawke and Julie Delphy meet on a train and spend a romantic night together in Vienna—talking, walking, philosophizing and falling in love. The twosome have an unstoppable chemistry and tremendous rapport with one another.
|2. It Happened One Night (1934) – It won five Academy Awards in 1934, set the gold standard for screwball comedies, and holds up as a timeless classic today. How many movies can claim that?Claudette Colbert is an heiress who has married fortune-hunting aviator Jameson Thomas, despite her father’s objections. Since then her father has been holding Claudette prisoner. She finally runs away and gets on a Greyhound bus bound for New York where she meets Clark Gable, a news reporter. They travel north together through a series of misadventures, and fall in love with one another.
|1. When Harry Met Sally (1989) – Bar none the best written and executed romantic comedy I’ve ever seen. Nora Ephron delivers a pitch perfect script with the best twists and turns. A beautiful concept eloquently translated by Rob Reiner. I am also a huge fan and even did an homage to the documentary couples interstitials that happen through the film.Billy Crystal and Meg Ryan share a car ride from Chicago to their new lives in NYC. They part ways on arrival and don’t like each other one bit. Five years later Billy and Meg share coincidentally share a flight together and again it ends in a similar result. Another five years later they meet again in a bookstore, and connect well enough to have dinner together. They become best friends, although he doesn’t believe men and women can be friends, and one night Billy goes to comfort Meg that accidentally turns into them having sex.