The Ten Best Romantic Comedies from 1998-2001

If one person typically becomes Twitter’s Main Character for a day with some rash or contentious take, on Monday the entire Ringer website became the social media platform’s unfortunate protagonist when its staff ranked “the 50 best romantic comedies in movie history.” “In movie history” is the key phrase there. Indeed, movies go back to the turn of the previous century and yet this list included but one romantic comedy released before 1980 (1971’s “Harold and Maude.”) “The Philadelphia Story” and “Some Like It Hot” and “Annie Hall” and “Roman”-freaking-“Holiday?” These were nowhere to be found. Such sorts of woebegone Internet listicles are not new, of course. Just a few years ago The Athletic’s ranking of the 100 greatest sports movies contained a single movie pre-1950 – “The Pride of the Yankees.” (It was #100.) These were sportswriters, however, and I’m more forgiving of such a modern bent with sportswriters. As disappointed as I am that college football writers spend the offseason scouring recruiting rankings rather than watching Golden Age college football comedies to expand their CFB movie scope beyond “Rudy,” I know that’s not possible. But while The Ringer might bill its site as “Sports” first, “Pop Culture” comes second. Its Head of Content has a Bachelor of Arts from Ithaca, known for a strong film program. Then again, The Ringer was created by Bill Simmons, who despite his penchant for classifying things in terms of All-Time is notoriously ahistorical. 

Not one of the greatest romantic comedies “in movie history.”

In the wake of the uproar, Ringer staffer Amelia Wedemeyer tweeted that the list was only “giving the piece more eyes and more clicks and more ad dollars.” This was awe-inspiring. She seemed to confess the list was literally nothing more than content. She has since deleted the tweet, completing the circle of social media, and maybe it’s best to view these weirdly modern rankings in that most depressing of lights – content, nothing more. It’s just a list, many weighed in as so many social media Copernicuses do, why do you care and why are you giving them the engagement, etc. I care because I think it is more than content, honestly, and not just because the participating staff seemed sincere in their various assessments. No, I think The Ringer’s 50 best romantic comedies “in movie history” is an incredible snapshot of where movie culture is headed…or maybe just is right now and for the rest of eternity. 

I don’t know the average age of the participating Ringer staffers and so I don’t want to completely cast aspersions here. At one time in my life I, too, would have thought the 1980s were the height of romantic comedies. But I overcame my incuriosity and that’s what troubles me – the incuriosity of anything old. When Roger Ebert began publishing his Great Movies in the 90s, I did not recoil at the ones I was unfamiliar with; rather I became intrigued to seek them out. They were a starting point, as Ebert himself essentially noted, as opposed to an end point, and the latter is how a list like The Ringer’s 50 greatest romantic comedies “in movie history” seems to function, not as a conversation starter or even in conversation with other lists but cordoned off from them, wholly subjective and of a limited viewpoint. In a vacuum, that’s not a bad thing. I love subjective lists! The more subjective, the better. But when you deem it the 50 best romantic comedies “in movie history,” that’s a whole other thing.

Steve Van Zandt has talked about how when he was coming up, bands would copy the bands that came before them in order to gradually find their rock ‘n’ roll voice. It was a connective tissue, in other words, from past to present to future, and that lists like The Ringer’s seem to suggest that link is also being severed with movies. Their sort of movie history feels in line with Disney stuffing its Fox Movies in the vault and not letting them out, Netflix restricting its classic movie streaming options to virtually nothing, and old film prints that are literally lost forever. The future has never felt further from the past. Anyway, apropos of nothing, here’s the ten best romantic comedies from 1998 to 2001.

The Ten Best Romantic Comedies from 1998-2001

10. Blast From the Past. I remember having one of those I’m-the-Only-Person-In-the-Theater-Laughing moments when Christopher Walken says “I was just examining the rear hatchway.” 

9. Love & Basketball. Honestly can’t believe this wasn’t on The Ringer’s list. 

8. Summer Catch. Appropriately, this was released at the tail-end of the summer of 2001, the wistfulness of summer’s end and the ostensible wistfulness of “Summer Catch” itself all cosmically underlining how this, unbeknownst to anyone at the time, this was essentially the end of the Prinze Jr. rom com run at the turn of the century. 

7. Simply Irresistible. I remember nothing about this one, which feels just right, its nondescript title an unmemorable representation of all the nondescript rom com titles of era (“Head Over Heels,” “Down to You”).

6. Never Been Kissed. Did you know Drew Barrymore is hosting a talk show now? What in the world is going on? I mean, maybe she’s happy as a talk show host, and Lauren Bacall bless her if she is, but is the Hollywood think tank really so dry we can’t muster up another a rom com for Drew. When I flew home from the Roman COVID hotel, I watched “Music and Lyrics” on the plane and let me tell you, it was something close to manna. 

This is “Music and Lyrics,” which is from 2007 not 1998-2001, but which I would probably throw on my Top 50 Romantic Comedies list. Maybe I’m as basic as The Ringer.

5. Drive Me Crazy. Melissa Joan Hart’s one crack at the rom com crown before turning 25 a couple years later which I guess rendered her a spinster in Hollywood Years. She’s been wandering in the wilderness of the Lifetime Channel ever since. 

4. Happy Accidents. Like Rob in “High Fidelity” sticks “Radiation Ruling the Nation” on his otherwise conventional Top 5 Side 1 Track 1 list, this is my chest-puffing curveball. 

3. Boys and Girls. The Prinze Jr. aficionados know “Boys and Girls” is the “Tunnel of Love” to “She’s All That’s” “Born in the USA.” 

2. Get Over It. A snapshot of how seemingly every Shakespeare play was at one point translated into a romantic comedy between 1998-2001, “Get Over It” was objectively (subjectively) the best not just because it starred Kirsten Dunst but because it also starred Martin Short and, wait, why haven’t they starred in another movie together.

1. Serendipity. Duh.