If I’ve driven home any point with this newsletter so far, it’s that I love the 90s. I was barely conscious for most of it, but there’s something about the decade that has has continued to keep a hold on me (and the world in general). People are nostalgic for lots of “old days” but there is a particular awe when they talk about the 90s. It was bright and fun, the economy was good, the world didn’t seem so scary. But the world post-1999 has felt like it’s in constant freefall. Nothing seems particularly promising. Maybe that’s why I can’t stop watching my favorite movies from back then.

In general, I love a teen movie and TV show. Even as a 30 year old, there’s something so wonderful about forgetting adulthood for a while as you lose yourself in something that reminds you of your youth. And even if you don’t have fond memories of those years yourself, for an hour and a half, or a multi-season binge, you can feel like you loved those years too. Actually being a teenage girl kind of sucked. Imagining I’m a teenage girl while watching 10 Things I Hate About You or Degrassi feels a little magical.

Of all the amazing 90s movies, are any more iconic than Clueless?

It is both easy and hard to describe the continued allure of Clueless. Critics tend to dismiss teen girl movies as unserious throwaways. Movies with women at the forefront can’t work, they said—no really, studio execs really thought it was too feminine.

But this movie did work, as is evidenced by its nearly three decade long appeal. And while most of us can’t relate to Cher’s incredibly rich, Beverly Hills existence, can’t we all relate to navigating the politics and hardships of friendships? And to do it in particularly iconic outfits nonetheless.

Movie characters, even teen ones, are often wise beyond their years. Sometimes it works, sometimes it’s exhausting. There is something refreshing about this particular group of teens being, well, clueless.

The Outfits

A few things came together perfectly to make Clueless the classic that it is. The wardrobe might be the top of the list. The fashion is not only a time capsule of a generation, but has been forever recreated in Halloween costumes, music videos, and everyday fits. Even Amber’s kooky style is worth admiring.

The Dialogue

No amount of incredible costuming would matter if the writing sucked, but the writing in Clueless is superb. It managed to use Valley girl, 90s slang that is forever quotable, but is also witty and downright hilarious. Think of any modern movie that tries too hard to use gen Z and alpha slang. The immediate cringe shines a spotlight on the poor writing. I’m sure people watching in 1995 thought some of it was cringey, but I still think about people in terms of Bettys, Baldwins, and Monets.

The Tech

They had a beepers. The cell phones were huge. But the closet. Are we kidding? I have dreamed of it my entire life. I’ve tried countless apps meant to digitize your wardrobe, but none can compare to Cher’s closet. Not only could you browse your collection via computer, but the actual closet also rotated around like in a dry cleaner. A girl can dream.

🧛 The Lost Boys: One of the best vampire movies, and best 80s movies period was released on July 31, 1987. It made my list of #Summerween watches, but it’s worth a rewatch any time of year.

🔎 Harriet the Spy: We don’t have enough movies about the trials and tribulations of the sixth grade, but Harriet the Spy, released July 10, 1996, chronicled the adventures of a New York City kid with ambitions of being a spy. And because I’m a Rosie O'Donnell stan, I dreamed of having her as my Golly.

👽 Men in Black: This is one great example of a movie that I think could have only been made in the 90s—July 2 1997, to be exact. It’s just funny and weird enough to continue to work 27 years later.

📦 Mystery Monsters: I’m convinced I’m the only person who saw this bizarre movie, with a 0% rating on Rotten Tomatoes. Somehow, though, I had it on VHS after it was released on July 29, 1997, and watched it constantly.

👭🏻 The Parent Trap: I think most modern kid movies are unfunny, relying on stupid jokes instead of genuinely great storytelling. That’s not the case with the July 20, 1998 remake of The Parent Trap. I’ve rewatched it twice this year and am still amazed by Lindsay Lohan’s acting chops.

🎥 The Blair Witch Project: On July 30, 1999, one of the most iconic found footage movies ever was released. It terrified and fooled people, who genuinely thought they were watching real footage from the recovered cameras of a bunch of missing filmmakers.

😱 Scary Movie: The 2000s were extremely unserious and that’s what allowed the parody movie series Scary Movie, the first of which was released on July 7, 2000, to thrive. The first installation poked the most fun at Scream and I Know What You Did Last Summer.