April 20 2022

The Top 5 Romantic Comedies Movies

As a self-proclaimed expert and lover of Romantic Comedies (“romcoms” if you’re cool), I could not let a recent article on the Ringer go by without a response. A few things to cover before I go into the rankings.

I’m only going to rank 5, because 50 seems like a lot of work and the vast majority of romcoms are in the solid to good range. I don’t have the stamina or heart to argue why 27 Dresses should be ahead of 13 Going on 30. They are both good movies that I’m sure I’d enjoy on rewatch, but don’t belong in the top 5 or have much in the way of discernable ranking difference.

Next, we need some clear rules on what a romcom is, and how they are being ranked. This is obviously subjective (read: the only accurate and definite list) but there needs to be a standard on why/how they are ranked:

A. The movie must be PG-13 or under. Rated R movies are, comedies, they aren’t romcoms, even if they follow the traditional formula. If you asked someone the genre of Knocked Up, There’s Something About Mary or Forgetting Sarah Marshall, 100% of people would say comedy. It’s unfair to traditional romcoms to go against these juggernauts that have the benefit of being more provocative and vulgar with the R rating. There are certainly exceptions to the rule (a movie like I Want You Back is a clear romcom and likely could have gone without the R rating), but this make things easier and standardized.

B. Rewatchability is key – Romcoms pretty much have the exact same formula, there’s a certain comfort in that. What makes a good romcom is no matter how many times you’ve seen it or where your starting point is, you want to continue watching it. The ups, the downs, the laughs along the way, are like a favorite homecooked meal, there’s something comforting in the predictability of it all.

C. The Turning Point/Reveal must be great – This is probably more a rule I just believe in, but the turning point must be a perfect combination, of funny and sad. One second you’re laughing the next second you’re crying. A romcom needs to nail this to get on my top 5 list.

On to the list…

5. This Means War

You’ll probably not find this movie on any other list. It has a pretty bad Rotten Tomatoes score (26% by critiques) and the back drop is more of an action movie. However, it’s a clear romcom with the central focus and plot being around the love triangle. It has great acting, its funny, it’s cute, and the characters are likeable and easy on the eyes. It does star Buddy Book Club’s arch nemesis Reese Witherspoon (listen to our The Last Thing He Told Me episode to understand why), but we’ll give her a pass for this one.

Turning Point/Reveal Rating: B+

4. Always Be My Maybe

Another sleeper movie that never got the publicity it deserved. Netflix has released a lot of romcoms, and a lot of duds. Unfortunately, I think this one kind of got ignored because of that. Big name studio actors (see the other four on this list) usually carry Romcoms. Ali Wong and Randall Park are two great comedic actors but have never been household names like Will Smith or Reese Witherspoon, but they crushed this movie. Great chemistry, comedic timing, and two characters you rooted for. Check this one out if you haven’t seen it.

Turning Point/Reveal Rating: A- (This probably isn’t the actual reveal but it’s one of the funniest romcom scenes out there):

3. Crazy, Stupid, Love

Most romcoms don’t have a lot of backbone but this both seems both like a real story and still has all the classic elements of a romcom. Every character seems to actually have a story (instead of having the 2-3 main characters with a few side characters that are just there for comic relief/exposition), and every character seems to be grounded in reality. Also, usually kids suck in movies, but they were solid in this. On top of the well-written story, it’s cast perfectly and super rewatachable.

Turning Point/Reveal Rating: A+ Unreal reveal and perfect mix of comedy and ultimately disappointment

2. How to Lose a Guy in 10 Days

When I think of a pure romcom this is the movie I think of. I’ve probably seen it a hundred times on TV, as it was constantly on and so easy to lose a couple (or 10…pun intended) hours watching. Matthew McConaughey and Kate Hudson’s chemistry is unmatched. It’s got all the elements you want, it’s perfectly paced and one of the most rewatchable movies you can think of. Matthew McConaughey does a much better job of telling you why it worked here so give it a listen instead. Also, his book is great, but I was disappointed he didn’t dedicate 100 pages to this movie (checkout our podcast on it).

Turning Point/Reveal Rating: A – The build up to this point is so good and it never disappoints, funny and sad all in one

1. Hitch

I know Will Smith is getting a lot of heat recently, but this movie is the romcom GOAT. Great premise, great execution, a ton of memorable funny scenes. Shout out to Kevin James in this, very funny. Hitch puts you on a constant emotional roller coaster. There are none of the traditional cringy romantic scenes or scenes that were slow/didn’t work. It’s funny, real and it’s an automatic rewatch anytime it’s on. Watch these two clips and tell me it’s not #1:

Turning Point/Reveal Rating: A+ I tear up every time watching this