Top Five X of 2001–2025: RomCom

I like movies and I like you

Apr 27, 2026

I have a few of these posts in various stages of incomplete (or dishabille, if you prefer). Each of them give different reasons for the project. As I work on them, I don’t know which will be posted first, so I’m letting their competing raisons d’être stand.

Anyway. Romcoms. Hard to talk about romcoms of this century coming, as they do, immediately after one of the great romcom eras: the 1990s. I also made my definition so strict that it became difficult to make it all the way to five:

‣ No kids in the romance roles. Ergo, no Moonrise Kingdom.

‣ Must have a happy, get-together-at-end ending of some sort for characters who were of primary importance throughout the movie. Ergo, no (500) Days of Summer, no Once I Was Engaged, no Love & Friendship.

‣ The rom must be the primary relationship of the movie. Ergo, no About a Boy, no Damsels in Distress.

‣ The rom must be the movie’s primary plot engine. Ergo, no Hundreds of Beavers, no The Muppets.

‣ The movie cannot be sold more as drama than comedy. Ergo, many 20th-century Jane Austen period-adaptations are out, no Anomalisa.

‣ I need to think of it as a romcom—other people thinking so is not enough—even if they are clearly correct. Ergo, no Fall Guy, no Eternity.

‣ Cannot be sullied by Rob Schneider. Ergo, no 50 First Dates.

Although I consider the romcom one of my favorite genres, I really haven’t watched that many of this new centuries’ entries. As I’ve worked on the list, I’ve discovered that I generally have low expectations for romcoms, even though many romcoms count among my very favorite movies of any sort.

Compared to some of the other lists I’m working on, my romcom longlist (fifteen movies) seems to have less issue with recency bias:

I thought it might have the opposite problem because the two movies that are absolutely inarguable came out in 2003 and 2004, but this looks fairly measured over time.

(Note, these charts might not match what follows. For instance, I decided Love & Friendship didn’t qualify—I think after I made the charts.)

One thing about romcoms is that they tend to be particularly rewatchable. But of the fifteen on the longlist, only six have I seen more than once (*), and some of those perhaps entirely because I sometimes show them to students (†). Because they haven’t been rewatched, I’m not sure I’m correct in my opinions. I’m relying on what I wrote at the time for some of them and hope I will agree with myself when given the chance.

In the end, I picked the movies because 1) I love them, 2) they are tippity-top rom, 3) they are tippidy-top com, 4) the rom and the com meld together in that wonderful way peculiar to the best romcoms, 5) I’m up for watching them again right now.

Which, if I were getting paid for this sort of thing, I definitely would have done first.

My top five, in order of topness:

Intolerable Cruelty (2003)* (thutopia)

I do not understand how many people—even fans of the Coen brothers—dismiss this movie which, for my money, is both one of their best films and the best romcom of the twenty-first century so far. The Coens’ trademark cynicism is not a sign that they hate of humanity, but that their cleareyed form of love insists on honesty and wit. Yes, these people are deeply flawed, but that doesn’t mean they don’t deserve love. We’re all flawed. But nobody needs berry spoons.

Win a Date with Tad Hamilton! (2004)*

We watched this movie so many times when it was new. And I still think that the central relationship is one of the best examples of friends that could be more. When I saw it, I wanted this team to adapt Byuck to film. Friends, confusion, hurt feelings, growing up, happy ending. Watch this movie, then count your beloved’s smiles.

Molli and Max in the Future (2023) (letterboxd, thubstack, thutopia)

This is the newest entry on the list and I am in love with it and I really really really need Lady Steed to sit down and watch it with me. Because of Molli’s brief pass through an alien sex cult (nothing explicit, just awkward) I haven’t wanted to watch it with the kids, but my wife needs to see this and have it be one of her favorites too. What is love if not sharing romcoms?

Stranger than Fiction (2006)*† (thutopia, thutopia)

This is the weirdest movie on this list by which I mean the romcom elements make up the smallest percentage of the whole—certainly less than half. It’s an existential nightmare and a commentary on art and a couple other things with a romcom. But to hit up an ‘80s classic, “Hey! Hello in there! Hey, what’s so important? What you got here that’s worth living for?” (“Truuuue looooove.…”) That’s something Stranger than Fiction believes as well.

Crazy, Stupid, Love. (2011) (thutopia, thutopia)

It was hard to make the fifth choice, but I went with the one I most want to rewatch at this moment. Even though I had mixed feelings about it back in 2014, I did dig it. I don’t even think the couple pictured is my favorite couple from the movie. But if you concentrate meetcute and mix it with tiny overcomeable tragedies and then bake to perfection, you get Crazy, Stupid, Love. Whatever its failings, when that’s what you want, this movie’s got it.

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