These classic comfort rom-coms hit different 25 years later

1999 was an incredible year for iconic movies. For many millennials, the rom-coms produced during this time have become touchstones for days when we just need something familiar and mushy to make it through.

Nostalgia is a hell of a drug because I have now been watching these movies for 25 years and I’m still not sick of them. What has changed is myself and the lived experience I now have as I view these films. When I watch these movies nowadays, I think about the way society has changed and how the films function within that context. It’s quite possible that some films wouldn’t fly now, and that’s probably okay. Change and progress are good things, after all!

Now, with a little bit of distance, let’s check in on some of the rom-com classics celebrating their 25th anniversary this year.

10 Things I Hate About You

This is the one. This is the G.O.A.T. 10 Thing I Hate About You is a retelling of Shakespeare’s Taming of the Shrew updated for a late-’90s audience. The Delia’s catalog? Extremely dog-eared. The soundtrack? There’s not a single skippable song on it. Kat was the closest depiction I would ever get to a riot grrrl which, of course, made her extremely cool to me. The way she shunned conformity and stood ten toes down for her beliefs and standards is still admirable to this day.

What breaks my heart when watching this movie is baby Heath Ledger in his breakthrough performance. So much talent and promise all lost to drug addiction not even 10 years later. I can’t disconnect it from the handful of friends of mine who are no longer here for the same reason. It’s a shame that lives are stolen this way, robbing the rest of us of some of the brightest lights on Earth. Thank goodness there is documentation of Ledger darting through bleachers singing, “Can’t Take My Eyes Off of You.”

At least Andrew Keegan isn’t a cult leader. That’s a relief.

She’s All That

She’s All That is another great example of a main character who unapologetically sticks to their own truth and standards. The world could use more depictions of a person willing to challenge the people around them when they’re being disrespected. Being fearless isn’t just about making rash decisions. Being fearless can also mean being willing to be the sole voice of dissent.

I have two words—Hackey. Sack. I think what stands out about this film now in comparison to when I first watched it is how it treated art. The performance art was a little tongue-in-cheek and read as “weird” and niche, no doubt to accentuate the vast difference between Laney Boggs and her popular, football-playing suitor, Zack Siler. To be a teenager is to be somewhat limited in exposure to cultural experiences. It was probably my first time seeing any kind of performance art. “Hackey Sack” kind of hit! And now, somewhat facilitated by online, short-form content, I live in a world where thousands of people would line up for hours to look Marina Abramović in the eyeballs. The weird girls are always ahead of their time. Always.

Never Been Kissed

Never Been Kissed is, by far, the hardest comfort rom-com to justify. Drew Barrymore is an undercover, 25-year-old reporter who goes back to high school to get material for a story and promptly falls in love with the English teacher. It feels like this shouldn’t have to be said, but since we’re still having the same exact conversations in 2024 CE, a teen cannot consent to be in a relationship with an adult. Double-no if that adult is their teacher. Even if the teen is willing, it is up to the adult to shut it down. He didn’t know she was 25! What was he thinking?

As a teen, I felt like the newsroom trying to get dirt on the teacher was the “bad guy” blocking two people who were made for each other from finding happiness. And to be honest, that’s how the film framed it. However, now that my prefrontal cortex has fully developed, I see that the newsroom was right! Jail! All the adults need to go to jail! Rob first! It took a little perspective to get here because I think a lot of teens struggle with boundaries. This movie functions as a time capsule of the unfortunate way consent was handled in popular media at the time.