Top 5 Romantic Comedies That I’ve Seen

Here’s a nice, little palate-cleanser in preparation for your Valentine’s Day evening.

When I was younger, romantic comedies were probably my second favorite film genre. As a guy who did not easily command the attention of the girls I admired, I yearned for evidence that I could be desired for personal aspects that went beyond my physical appearance, which to this day leaves much to be desired. So it made sense that I gravitated towards romantic comedies, which often show awkward underdogs landing women that are several echelons out of their league by being able to offer something more valuable and genuine than looks, riches or popularity.

In later, more recent years, I’ve moved away from the romance genre for the most part. I started to notice an insidious theme underlying the true love that was being promoted via the main story – someone else was being screwed over so that the main couple could be happy. Consider The Notebook and the fate that befalls Lon (James Marsdon). He thought life was peachy until Allie (Rachel McAdams) sees a recent picture of her old boyfriend, Noah (Ryan Gosling), from seven years ago and suddenly she cheats on Lon and calls off the wedding. I suppose this would be OK if Allie had a longer history with Noah rather than three months and if Lon was a jerk rather than an all around great guy. Also consider Sleepless in Seattle. Here’s poor Walter (Bill Pullman) losing his fiancée, Annie (Meg Ryan), because his name is too formal and because Annie hears some guy’s voice on the radio. Now I understand that the point of these films is to focus on the “true love” of the main characters, but how can people not realize that that love is built upon a foundation of broken hearts?

That’s not to say, however, that romantic comedies (I’ll steer clear of romantic dramas for now) can’t be compelling cinema with a wholesome story that doesn’t present a romantic zero-sum game. Here are five romantic comedies that I enjoy, that I can think of and that I can remember enough of their plots to share them today. In no particular order:You’ve Got Mail (1998)

Joe Fox (Tom Hanks) has an Internet relationship with Kathleen Kelly (Meg Ryan). They don’t disclose any personal information or exchange pictures. Their attraction is solely based on personality. In real life, they each have their significant others and are business rivals. When Joe discovers that Kathleen and his Internet “friend” are one and the same he makes a concerted effort to win her heart, but it’s difficult when Kathleen is in love with his Internet persona, but despises him in real life.

This movie almost didn’t make the list, mainly because Joe and Kathleen are essentially cheating on their real life relationships. Granted, it’s not physical – it’s not sexual in any way – but it’s the other side of cheating: the emotional side. Rather than addressing what’s missing in their real life relationships that’s forcing them to seek this virtual relationship, the two “heroes” sneak around online, typing furiously while their pulses race through their veins. Fortunately, the film redeems itself by having these characters break up with their real life significant others in a natural way that is independent of the main love story. Everything else about the movie is top notch. The cast is great, the vignettes are poignant and the comedy is fun. Furthermore, Tom Hanks and Meg Ryan just make for a great couple and who doesn’t want to see that?Some Kind of Wonderful (1987)

I’ve only seen this movie once, but this John Hughes film had a lasting impact on me, because the main character, Keith (Eric Stoltz), reminded me of me. He’s a high school student that’s enamored with a beautiful and popular girl named Amanda (Lea Thompson). Keith doesn’t know exactly how to win her over so he teams up with local tough-chick Watts (Mary Stuart Masterson) and concocts an elaborate plan to romance Amanda into liking him. Forgive me if I’ve butchered the plot. Like I said, I’ve only seen this movie once and I was a child at the time.

Anyway, what really got this movie stuck in my head back then was the fact that Keith was an artist, like I was an artist, and we both drew portraits of the girl we wanted. I loved the scene with Keith getting himself into detention just to be with Amanda who also got detention that morning. Little does Keith know, however, that Amanda used her charms to get out of detention, leaving Keith with the dregs of high school. Through his artistic ability, Keith befriends a skinhead (Elias Koteas) who carves a relief into his desk to join Keith’s artistry. Now that I think about it, I do recall being disappointed with the ending. I should probably give it another viewing to see how I feel about it now.High Fidelity (2000)

Rob Gordon (John Cusack) can categorize everything in his life within a Top 5 list. When the film starts, he’s going through a break up with his live-in girlfriend Laura (Iben Hjejle), but refuses to be affected by it, believing that she doesn’t even make his Top 5 list of relationships. The story is a path to self-discovery as Rob sorts out his feelings with his friends Dick (Todd Louiso) and Barry (Jack Black) and copes with the reality that Laura is with a new guy named Ian (Tim Robbins).

High Fidelity appeals to me on many levels. First, I like the way the story is presented, with a narrator that’s prone to fantasizing onscreen and continually breaks the fourth wall to speak directly to the audience. Furthermore, I like how the film presents modern day relationships. They’re messy, complex and confusing. It’s very rare to find someone who’s perfect for you, but that’s why relationships require work and commitment to keep it going.When Harry Met Sally (1989)

Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) are polar opposites when it comes to personality. Strangely, they keep running into each other throughout various stages of their lives. In this weird, roundabout manner they discover that the path to true love is sometimes arduous and not always straight.

This is one of those ubiquitous films that I had to include to keep my credibility. On the other hand, When Harry Met Sally still holds up today in both the romance and the comedy departments as well as the general presentation. In 1989 the social truths like “men and women can’t be friends, because sex gets in the way” and “all women fake orgasms” were groundbreaking and refreshing. Today, they’re foregone conclusions. Nevertheless, you get to see Billy Crystal in his prime and the short interviews with the fictional couples presented documentary-style give the film just enough texture to make the story a classic.Swingers (1996)

Mike (Jon Favreau) is going through the recovery process of a tough breakup. It’s been six months, but he still can’t get over his ex-girlfriend. His friends, Rob (Ron Livingston), Trent (Vince Vaughn) and Sue (Patrick Van Horn), encourage Mike to get back into the dating game with mostly terrible results. Swingers follows Mike as he turns the corner in his single status and decides he’s ready to pursue a new relationship, but in his own way and in his own time.

This is another one of those ubiquitous choices, but I’m sure that many people who appreciate romantic comedies probably wouldn’t include Swingers as part of the genre. I think that’s the case because there’s no real romance – at least not for most of the movie. I include it in this list because pursuit and transition are big parts of modern day relationships and not many movies cover these aspects. For a lot of young guys who are still in the pursuit stage of their lives, Swingers is a reflection of their reality. I know that I caught myself yelling, “That’s SO true!” more than a couple of times when I watched this movie for the first time.Notting Hill (1999)

Anna Scott (Julia Roberts) is currently the most famous actress in the world. William Thacker (Hugh Grant) is no one. By chance, Anna walks into William’s travel book shop and they strike up an impulsive romantic relationship. Unfortunately, Anna’s celebrity life is complex and doesn’t permit for the convenient relationship that William is looking for. Nevertheless, perhaps their common desire for a normal life together can surmount the tremendous obstacles that keep their love from blooming.

First of all, I know this is #6 on a Top 5 list. It’s my list and I can break the rules if I want. Secondly, if I had to pick a favorite romantic comedy it’d have to be Notting Hill. Not only is it tremendously funny, but the acting is pitch-perfect all around. Well, maybe that’s overstating things, but I think the acting is close. My favorite scene is the birthday dinner as these average, normal people adjust to having an A-list celebrity sitting with them. (It’s remarkably close to how I felt during my first few roundtable interviews.) The tone in that scene is amazing and the emotional current ebbs and flows from touching to comic to deadly serious, back to lighthearted in the end. Also, who can’t appreciate the stylized, one-take, transition scene with Hugh Grant walking along as the seasons change around him? Finally, one point of contention with the ending: I’ve never seen that many journalists with their own SLR cameras at a Press conference.Strays (1997)

Rick (Vin Diesel) is a player. He runs around with his player friends and they pick up as many chicks as they can and sleep around. Rick, however, has a pretty good head on his shoulders and is trying to turn his life around with a new, wholesome girl he meets, Heather (Suzanne Lanza). Unfortunately, his lifestyle and his learned behavior keep getting in the way.

This movie is just barely a romantic comedy and I don’t even care for it that much. I just threw this movie on this list for those people who had a problem with me going to six. IN YOUR FACE! HERE’S #7! Also, I just think it’s absolutely hysterical that Vin Diesel is in a romantic comedy. He even serenades a girl. Check it out if you want to see Diesel’s early work.

Happy Valentine’s Day everyone!