Old movies about teenagers tend to look unbelievably naive now because they are almost always free of any direct references to either sex or drugs even though both of those things have always been a part of every young person's learning curve. On the rare occasions where sex or drugs did come up in old movies their treatment tended to be completely unbelievable - more often than not the insinuation would be that every sexual encounter lead to pregnancy and every puff of a marijuana cigarette led into addiction. Now that our culture is more willing to be frank about those taboos movies which completely omit those subjects or which distort them in propagandistic ways seem overly sanitized and out of touch.

However, I'm not so sure that we should be too quick to give ourselves a pat on the back for being more sophisticated than our forebearers because it is quite possible that our modern teenage movies will look equally naive or dated to future generations. Take Clueless, a comedy from 1995 about a sixteen year old girl named Cher. Now, Clueless is definitely not naive in the same way those old movies are naive -  this movie features plenty of matter of fact sex and drug talk. Cher and her friends are open about who is a virgin and who isn't, and when one character finally goes all the way it is mentioned in one line in the voice over and then dropped entirely as if it just wasn't that big of a deal. Clueless also has a few jokes about cocaine and there is even a scene where Cher and her sidekick Tai smoke a doobie at a party but then that's that - there are no downsides to their casual drug use. It's all treated in a relatively blase manner, acknowledging that kids do these things but without judging them for it.

Despite those worldly touches, however, Clueless still seems rather innocent from the perspective of 2015, and that's mostly due to the way it portrays its main character. Cher is your classic rich kid who lives to shop, who feels entitled to good grades she hasn't worked for, who knows nothing about the maid that has been living in their house for years and years. (Cher thinks she's Mexican when she's actually Guatemalan.) Clueless depicts Cher as slightly daffy but fundamentally sincere young woman, and it depicts her adventures as being harmless and charming. However, I found it hard to look at this movie and see either her or her actions that way. You see, in the twenty years since this movie came out there have been dozens of reality TV shows about people like Cher, and all of them have sort of poisoned how I think about the idle rich. I can still watch this movie and appreciate it for being so sunny and pleasant - but I can't watch it and not think about how unsophisticated it's portrait of Cher is.

For example, Cher is constantly playing matchmaker with her friends and teachers. She tries to manipulate two teachers into getting together by sending them fake love notes. She tries to steer her friend Tai towards a rich doof named Elton and away from the stoner that she obviously likes more. She tries to make the new boy in class jealous by sending chocolates and flowers to herself. No one ever resents Cher for these petty manipulations, in large part because they all work out well in the end. The teachers find love; Tai finds love; Cher finds love. But that sort of unnecessary pot-stirring is actually a lot more troubling than this movie lets on. If a Real Housewife did something like that it would almost assuredly blow up in her face, not just because the people on those shows are primed to make mountains out of molehills, but because people tend to not like it when they are treated like they were someone else's plaything. Cher's sweet intentions don't cover up the fact that her every action she takes has the real potential to cause serious drama - drama that is definitely going to happen if she keeps being a busybody.

Or consider Cher's "philanthropy". Clueless is in large part about how Cher goes from being a self-absorbed spoiled brat to being a well meaning spoiled brat, and one of the final scenes has her leading a charity drive for the "Pismo Beach Disaster". The big joke is that she has no idea what supplies to give poor people in need - she donates a set of skis, and when her stoner friend tries to donate a bong made out of a hollowed out honey bear she tells another assistant to "file it with the kitchen stuff." It is a funny scene, and I don't want to be dismissive of this film's sweetness, but I did find this film's endorsement of her overprivileged cluelessness to be kind of hard to swallow. We live in a post-Paris Hilton world; in a world where the Kardashians are less popular even than our worthless Congress; in a world where rich plutocrat Mitt Romney thinks he can help all of America despite his utter contempt for 47% of it's people. Clueless's jokes about the bubble that rich people live in were probably fine in 1995, but at this point I know too much about the 1% to give a rich person a pass because they "mean well". Now I want them to actually do well. Since Cher's attempts at charity were obviously fundamentally worthless her instant self-congratulations was as galling as it was amusing.

The fundamental problem with Clueless is that it is to some extent a satire of a certain type of awful person, but it is too nice of a satire. This movie is fully aware that the Chers of the world are incredibly shallow and thus slightly problematic, but at the end of the day it's sympathy does lie with it's characters. That attitude was more acceptable twenty years ago when Valley Girls were obnoxious but not the end of the world. Now, however, this film's fundamental toothlessness seems rather dated, because the rich-brat archetype has evolved into something far more toxic, and Clueless is just too much of a surface level story to address those thorny undertones.

Ultimately I doubt that Clueless' reputation will stumble too much in the years to come. It is a solid portrait of female friendship and as such it will always appeal to women. Furthermore it is an interesting time capsule of the 90s and as such it will always appeal to people who are nostalgic for that time. However, it is definitely a nostalgia piece now, since everything from it's soundtrack to it's fashion to it's overall attitude makes it seem feel like a time capsule that is offering you a glimpse of a bygone era. I just hope that when future generations watch this they will give it some credit for it's frankness, instead of immediately writing it off because it's cell phone technology is so ancient that it precludes sexting, even though it's parties are completely molly-free, despite the fact that it's whole carefree vibe screams "9/11 HASN'T HAPPENED YET Y'ALL." Because call me naive if you want to, but I kind of want to believe that my generation is always going to be in-touch with what the kids are all about, even if we are getting all of our information about teenage life from twenty year old movies that weren't even that realistic when they were brand new.

Winner: Me

Clueless on IMDB