Top Five: Movies To Watch With Your Sweetie

Valentine’s Day is upon us. Or Singles’ Awareness Day. Either way you look at it, this is supposed to be the most romantic day of the year. Thus, I’m dishing up five films that are both romantic and funny, the best combination for some Valentine’s Day magic. Any of these would be great to watch cuddled up on the couch with your special someone. Or you can watch them alone with a big tub of ice cream, as I usually do.

1. “When Harry Met Sally” (1989)
There is a reason that this movie is such a great romantic comedy. Nora Ephron has written a slough of these things, but nothing quite matches with this wonderful film. And with Rob Reiner in the director’s chair, how can you go wrong? Billy Crystal and Meg Ryan are the title couple, following the story arch set in perhaps the most romantic city, New York. The film is a great look into the concept of platonic relationships, something that both Harry and Sally desperately want to pursue, despite being absolutely perfect for each other. Oh, and when Meg Ryan gives the fake orgasm in the world-famous Katz’s Deli, everyone saw the rules of comedy changed forever.

2. “Annie Hall” (1977)
Once again, this film is set in New York. Woody Allen used the city as a backdrop for a film that broke from his previous trend of laugh-out-loud comedies. “Annie Hall” is quite funny, but the film transcends mere humor and reaches a point where it explores the intricate nature of human relationships. Allen plays the hero, Alvy Singer, and Diane Keaton is fantastic as the title character. The film follows the entire cycle of their relationship, from their first meeting to the eventual break-up and beyond. The dialogue is so pure and earnest that watching the film is almost like watching your brain at work. Allen breaks the “fourth wall”, and speaks directly to the camera several times, making for some of the best writing in modern cinema. And Keaton’s layered attire defined a generation of women’s clothes.

3. “Jerry Maguire” (1996)
Say what you will about Tom Cruise now, but he used to be one of the best. Not only does “Jerry Maguire” have one of the best romantic stories of all time, it features sports prominently. It is because of this that this film is perfect for the couple that can’t agree on a movie on a Saturday night. Cruise is the title character, a sports agent who loses all his clients save for the obnoxiously loud football star Cuba Gooding Jr. Renee Zellweger is the one woman who actually believes in Jerry, and, in the end, the one woman that can complete his life. Director Cameron Crowe used to write for Rolling Stone, so naturally the music is amazing. Also, don’t forget the two lines of dialogue that defined the ‘90s for many, many people: “Show me the money!” and “You had me at ‘Hello.’”

4. “Love Actually” (2003)
This movie is basically a showcase of talented British actors. Let’s see who we have: Alan Rickman, Emma Thompson, Hugh Grant, Colin Firth, Liam Neeson, Keira Knightly, Laura Linney and Bill Nighy. Here’s the thing: THAT’S NOT EVERYONE. The massive cast is used to portray multiple stories of people falling in and out of love in London, England. Despite it’s length (over 2 hours), the film moves swiftly thanks to clever writing and excellent acting. It is simultaneously sweet and sorrowful, happy and sad. In the end, though, you are left with the feeling that everything has ended with the best. Oh, and in case you were worried, “Love Actually” will make you laugh.

5. “Some Like It Hot” (1959)
No list of romantic movies is complete without some solid cross-dressing. Jack Lemmon and Tony Curtis disguise themselves as members of an all-girl band on their way to Florida so as to avoid a Chicago gangster. Sound ridiculous? It is, but it’s so well done that nobody cares. Of course, they run across Marilyn Monroe while disguised as girls, thus leading to plot complications that would give Shakespeare a headache. Curtis assumes another identity just to get closer to Monroe, while an older male millionaire pursues Lemmon-in-drag. The laughs come hard and fast, and Lemmon and Curtis are spot on as they deal with the implications of their assumed identities. Heck, even if you don’t like their humor, you get to spend 2 hours looking at Marilyn Monroe, so who are you to complain?