11 Jerry Maguire
Jerry Maguire was a powerhouse when it came out. It stars Tom Cruise when he was at the height of his pre-freakout part of his career. So far it was also the height of Cuba Gooding Jr.’s career and the movie even got him an Academy Award. The one is probably the most critically acclaimed movie on this list and it won or was nominated for a lot of awards. It has a great cast with Cruise, Gooding Jr., Jerry O’Connell and a great villain in Jay Mohr. A lot of the movie is focused on the title character trying to regain his honor and his career after a huge professional setback. There is plenty of romance, though. Unfortunately, a lot of this movie has been heavily quoted and the movie’s tropes have become very cliche. At the time, it felt pretty original. As a warning, it has some pretty graphic sex scenes in it that I was not allowed to watch when this first came out. Other than that, it’s a pretty fun movie.
10 Alex and Emma
Go figure that a romantic comedy movie about a writer would be on this list. I guess I have always identified with writers. Also, a big part of this is a deadline which I think we are all far too familiar with. Now, I’ve never really been one for writing romance but the main character is a writer played by Luke Wilson who enlists Kate Hudson to help him work through his latest book. So we get them working on the book and that is juxtaposed with scenes from the book. The two stories contrast and fit together and we get to see a lot of the growing chemistry between Kate and Luke. This was only the second romantic comedy I saw that more or less had a male lead. Of course, Luke is the guy who must change to get the girl he needs instead of the one he wants. It’s a cute little movie that has a bunch of interesting twists to it.
9 Coming to America
Most of you have probably seen this movie already. It’s often in rotation several times a year on Comedy Central and it was a big hit around the time of Trading Places. It comes from the brighter part of Eddie Murphy’s career when he regularly picked better movies and was not yet a caricature of himself. Ok, I am mostly kidding because Eddie Murphy often gets a bad rap even though he has made some great or at least fun films along with a string of bad ones. This is the tale of an African prince who journeys to America to figure out his path in life and to try and find a wife. The movie is surprisingly subtle for both the times and for Eddie Murphy. There is an interesting fish out of water story mixed with a story about a man hiding what he is for benevolent reasons. The movie is funny but not at the expense of the story moving forward. It ends up being a pretty sweet movie with a tight little love story.
8 Shakespeare in Love
I love the plays of William Shakespeare. My early days in theater were spent doing a lot of Shakespeare plays and they were so fun to do creatively. This movie was a massive hit when it came out, it was nominated for and won a lot of awards and for good reason. I love anything that humanizes Shakespeare. I don’t like ‘updating’ classic literature as much as I like when that literature is brought to life. Romeo and Juliet is arguably one of Shakespeare’s worst plays but mostly because people misinterpret it. It is a play about the excitement of lust and new love and the insanity it can cause. This is the backdrop of the movie, a romance set in an obviously romanticized Elizabethan era while Romeo and Juliet is being made. Almost everybody is somebody you could read about in a history book but they feel like a real person. They didn’t whitewash Shakespeare’s real history either at least not much. As I get older, I have learned to really embrace the ending as a happy one.
7 Zack and Miri Make a Porno
Now hold on, don’t leave right away. I promise I won’t go int the porno part of this movie if you don’t want me too. It’s enough to know that this one is about two broke roommates who decide to make a cheap porno spoof to pay their bills. There is a lot of wackiness involved and you get a lot of sexual humor and humor based on the awkwardness that we feel around sexual humor. It has a cast of supporting characters who are zany but human and it’s really fun to see them all interact. However, above it all is a story about two people who have known each other a long time. Two friends who explore whether they might be more in a very interesting set of circumstances. Like a lot of Kevin Smith’s movies, I went in expecting a silly stoner comedy and I came away with something that felt really interesting. Who says friends can’t become a couple? (Fair warning there is some nudity in this one)
6 Catch and Release
So I watched this movie initially because of Kevin Smith’s involvement. It certainly did not hurt that the movie also stars Jennifer Garner who I had liked in Daredevil and Timothy Oliphant who I had enjoyed in Die Hard 4.
This was probably the first or close to first romantic comedy that I watched on my own recognizance. I will give you a heads up here, this one looks weird on paper. It starts with Jennifer Garner’s fiance dying on a fly fishing trip and then goes from there. The relationship between Garner and Oliphant is pretty funny and interesting to watch as there is a strange dynamic from the start. On top of that, there is a B-plot where Kevin Smith romances a single mother with a kid. The two stories are fun to watch separately but watching them interact is even better. I know this one is kind of an obscure pull but I really enjoyed it.
5 Chasing Amy
Alright yes, three movies in a row on this list have Kevin Smith involved but it is a known fact that I am a big Kevin Smith fan. More than any other movie, this was the one that broke Smith into the mainstream studio system. For this movie, we delve into the exciting world of comic books which is a topic near and dear to my heart. Two of the main characters make comic books for a living and you know Kevin Smith has been in the industry because everything about that feels right. The movie is a little bit of a product of its time. There is a flamboyantly gay black man in a time when there were a few of those sorts of characters in Hollywood. Kevin Smith is so great at dialogue that even the more cliched characters come off as real and likable. The main part of this movie is that Ben Affleck plays a guy who ends up dating a lesbian. While some people thought it was a little crass at the time, I think it was a little ahead of its time in depicting the unpredictability of the Kinsey scale. Of course, that’s just my opinion.
4 Groundhog Day
This is technically the only science fiction movie on this list. I would also classify this as a dark comedy while most of the rest of these movies are at least a little bit lighter. Bill Murray is a comedy legend and is very funny as a man who is trying to decide what is important. The universe makes him repeat the same day over and over again until he achieves what he is supposed to. Andie McDowell is a great romantic lead. She is cute, funny and appropriately skeptical as a formerly grump starts to become a romantic. Another strength of the movie is that it has a great ensemble of character actors who interact really well with Bill Murray. I feel like the movie is about discovering that love is not checking things off a list but is more about realizing how to make a real human connection. I am sure most people reading this have already seen the movie but it is worth checking out if you have not.
3 Forgetting Sarah Marshall
I was totally blindsided by this movie. While I had heard that it was a good movie and that it was worth seeing, I had no idea how good it could be. I actually watched this movie for the first time this week so it is the freshest in my mind. Ten minutes in and I was definitely hooked. The cast is fantastic as it has Jason Segel, Kristen Bell, Mila Kunis, Russell Brand and a whole bunch of great actors in smaller parts. I especially love Kristen Bell and the meta references to Veronica Mars which was one of my favorite shows of all time. Segel shows why he was able to rock it in The Muppets as he is the star and the writer of the movie. Frankly, more of this movie is about break ups rather than new relationships. Everything really clicks together and there are a lot of moments where I felt like the movie had really shown what had been in my heart during my most awkward moments. It may have the best message at the end of all the movies on this list. (Fair warning there is a lot of nudity in this one)
2 Love, Actually
This movie is a Christmas tradition for my family. My mom actually owns three copies of it on DVD. This movie is actually pretty atypical in structure for a romantic comedy. There is a huge cast of characters that make up a whopping nine couples who the audience gets to follow. At times, the movie seems to employ just about every actor in England which is the setting for most of the movie. A couple movies like Valentine’s Day and New Year’s Day later tried to use this formula to zero success. Love, Actually is a really charming movie. There is a bitter, sardonic edge to a lot of the humor that makes it feel emotionally true even if some of the plots are contrived. I am trying to spoil as little as possible with this list but it is important to note that not all of the stories have happy endings. Not all of the stories and couples are even very likable but the movie as a whole is very cathartic and is always a good watch.
I have talked about this movie previously in this blog, shortly after I saw it in theaters. Amy Schumer is a great comedian who works very blue and also works very dark. She manages to make a lot of that subject matter way funnier than it should be. There is also something to the cadence of her voice that is just inherently funny to me. Combine that with the great, befuddled straight man in Bill Hader and you’ve got a beautiful match. The movie uses a lot of modern romcom tropes and dumb comedy tropes but it manages to strip them down and make them feel more real. There’s real drama and at the end of it, both people in the relationship have changed their lives for the better in a deeply transformative way. It’s really ugly to watch but it’s beautiful too and I feel better for having watched it.
Tags: A to Z, A to Z Blogging Challenge, Alex and Emma, Catch and Release, Chasing Amy, Coming to America, Forgetting Sarah Marshall, Great Movie, Groundhog Day, Jerry Maguire, Love Actually, Romantic Comedies, Shakespeare in Love, T, Top 11, Trainwreck, Zack and Miri Make A Porno