The 40 Year Old Virgin- The film that launched Steve Carrell into the stratosphere. Here he plays, well a man who is 40 and has never had sex. He doesn't quite know how to deal with that and once his co-workers find this information out they take it upon themselves to offer up assistance at every turn. Andy, smartly, does not listen to what they say and instead decides to pursue Trish the old fashioned way by leading with his winning personality and pushing the physical nature of the relationship to the background. Charming, smart, and most of all funny.
The Wedding Singer- While earlier movies may have been funnier this was Sandler actually putting together a solid story with the humor. It ends up creating the Sandler comedy that actually has some heart behind it. Also, the film is about as cute as Drew Barrymore has ever been. She is so sweet here in her role of the girl being put upon by an obvious loser of a man. By the end you want her and Sandler to get together and you get that in a nice little sequence involving Billy Idol.
Romancing the Stone- Don't let the poster fool you where it makes the film look like an adaptation of a romance novel. Kathleen Turner plays a romance novelist who comes into possession of a treasure map which some diamond smugglers want as ransom for the safe return of her friend. When she gets into trouble she is saved by an American swashbuckler played by Michael Douglas. From there it turns into an adventure film with the romantic relationship at the heart of it. Good performances all around, most importantly by a scene stealing Danny Devito.
10 Things I Hate About You- A modern adaptation of Shakespeare's Taming of the Shrew this is the rare high school comedy that is fairly intelligent. Joseph Gordon Levitt's character wants to date Larisa Oleynik's character but she can't date until her older sister (Julia Stiles) dates per her dad's wishes. So a plan is set in motion to get the school outcast (Heath Ledger) to romance Julia and make it so everyone can date happily. Funny lines abound, some great performances, and you get to see Ledger show off the traits that would make him a huge movie star.
Forgetting Sarah Marshall- Get past the first 10 minutes or so where you see a little too much of Jason Segel and you are left with a movie that is a situation every guy has been in. Every one has had their heart broken and Segel here takes a beating from his celebrity girlfriend. When he tries to get away he only finds that they are within feet of each other. So he finds solace in island resident Mila Kunis and so begins a relationship where Segel is trying to put himself back together and win over a beautiful woman. It's a story about a man trying to regain his confidence once it has been shattered and it is hilarious throughout.
Before Sunrise/ Before Sunset- Hard not to put these films together since they both focus on individual periods of time with the same couple. In Sunrise, Hawke and Delpy's characters meet on a train and he convinces her to get off the train at his spot and hang out with him for the night enjoying each other's company and seeing what they could have with each other. The longer they are together the more in-depth their conversation gets. When they eventually have to split they recognize that this was perfect and they may never see each other again but they do have the past night. In Sunset, they meet up again and again are constrained by time while spending time with each other. They realize that deep down they have a connection to each other even if factors are pulling them in different directions. By the end they make decisions but the ending is sort of left up to the viewer as to what will happen exactly. Essentially the writing is arguing that the ending is our own creation and we choose the path. It is a talky film, but it is smart, and truly represents what love can be when we want it to be that.
There's Something About Mary- Everyone in her life is crazy about Mary. People try to win her heart through deceit and lies. Others try to win it by being caring thoughtful individuals. This film is hilarious throughout and features some scenes that will leave you short of breath from laughing so hard. The key here though is that the girl at the center of the film has to be that desirable. Cameron Diaz fits that role in every way. She is pretty, smart, funny, caring, and is a huge fan of sports. Mary here is perfect in about every way and by the end you can see while everyone is trying to be with her.
As Good As It Gets- Jack Nicholson is an old crank who is trying so hard to be someone more than what he is. The catalyst for that change is the waitress at his favorite restaurant played by Helen Hunt. In their first film interaction he finds a way to offend her and she responds by putting him in his place. To that point he viewed interaction with other people as a chance to continually insult them. After that interaction he decides he wants to change the way he is so he begins trying hard to become a better person in an attempt to win over the waitress. He constantly trips himself up when he gets close and by the end you see no way he will pull this all off. Part of the fun of the film is that journey.
Chasing Amy- The voice of Generation Y deserved a spot on this list. This is arguably Kevin Smith's best work. It is a relationship that has no chance of working because the two characters involved are obviously oil and water in so many ways. They have some similarities but they are really defined by their differences and that is a tougher bridge to cross. This is about a man who is trying to fit a square peg into a round hole (metaphorically). This film is like many of Smith's other works but there is a deep subtext running here as you can tell Smith is laying open his own scars for everyone to see (This film was famously based on his own relationship and feelings of inadequacy in a relationship with Joey Lauren Adams). There is a scene in the middle though that will get to most guys as Affleck's character lays his heart out there to Adams trying to win her over. In the end it is a futile attempt which makes it all the more painful to hear it.
Serendipity- The John Cusack portion of the proceedings begins. This is the film that is probably the closest to a traditional romance movie on this list. Cusack and Beckinsale plays two people that meet through quirky circumstances. They begin playing a game then to determine if fate is trying to push them together. Fate is but man's intrusion on fate keeps them apart initially. Years later they meet up again through fate and begin an attempt to start a relationship even while they are both with other people. It's cheesy at times, but Cusack is such an endearing actor that he has a knack to help guys put themselves in his shoes during the film. Plus, you get to look at Kate Beckinsale for 90 minutes.
Say Anything- The Cameron Crowe film that made him a household name as a director. It is also the film that launched Cusack as a leading man after some nice, but unspectacular roles. An underachiever begins chasing after the valedictorian after they graduate high school. Ione Skye's character is intelligent but socially awkward and can't believe that Cusack's character would even be interested in her. They begin a relationship even while her dad disapproves. This is a film about how honesty, and the the lack of honesty can affect a relationship. This is a movie but Cameron Crowe writes this as if it is happening in real time where we are noticing all the intricacies of how the world is altering our characters. A great film and features one of the most iconic moments in film.
High Fidelity- When his girlfriend breaks up with him Cusack's character turns on himself. He realizes that as more and more women break up with him HE must be doing something wrong. He is a self described audiophile so he begins discussing his love of music and tries to find some answers through that spectrum of thought. He analyzes all of his past relationships trying to figure out where things went wrong. I probably identify with this film entirely too much but I love this movie and this is my favorite of the Cusack films listed here.
The Princess Bride- If you know me, it should come as no shock when I say that this film is on the list of my favorite movies ever. It has everything: romance, action, comedy, and some great performances by some great actors. Princess Buttercup and farm hand Westley are in love with each other but due to their circumstances they can never be together. Being that it is a film though you know the concept of the movie is finding a way to get them together. I could go on and on about the film but truly it comes down to one of the slogans for the film which is, "True love has never been a snap." And truly it isn't. You suffer heartbreak, loss, and rejection constantly hoping you come out on the other side with someone you love and care for. This film believes whole-heartedly in that idea and surrounds it with monsters, trolls, and sword fights. If you've never seen it, this Valentine's Day would be a perfect opportunity to fix that mistake.
