Y2K didn't destroy everything — but it did usher in an unbelievably messy era of pop culture

Anne-iversaries is a bi-weekly column by writer Anne T. Donahue that explores and celebrates the pop culture that defined the '90s and 2000s and the way it affects us now (with, of course, a few personal anecdotes along the way).

The 2000s were a full-on Monet — a big ol' mess. They were defined by Von Dutch hats and long, skinny scarves and peppered with dance movies (a treat) and Star Wars prequels (less so). They were an amalgamation of leftover 90s-era gloom melded with the cheap sheen of what we'd hope would be a shiny happy future (a myth spurred on by the promise of a new and improved slate thanks to a new century). But of course, outside the polish of the reality television du jour, the future didn't necessarily end up being shiny or happy after all — and the decade's pop culture reflected that.

The 2000s, more or less, were the cultural equivalent of an antique market: on the one hand, there was cinematic history, TV-based treasures and music that helped define the era. On the other, there were seashell necklaces, Jersey Shore and the last season of The O.C. (The first two were high art, and the third I'm still trying to wrap my head around.) The decade was all over the place. And to be honest, I hated it.

More specifically, I hated it while I was living through it. Like the 2000s itself, I was exactly as disjointed as those cursed years were, particularly as my 20-something self tried to decide who I was, what pop culture I should like, how I wanted my hair to look (spoiler alert: "bad," apparently) and the type of adult I was hoping to grow into (I'm still figuring that one out). In terms of culture, the decade signalled a shift from the sweeping epics, coming-of-age stories and action-adventures we'd gotten to know in the 90s (predominantly tales without the internet or stories about it, which made it all feel a little more self-contained) to pop culture that expanded on the future, identity crises, and the good and bad that technology can bring. All in all, it was a nightmare — especially when using it as a guide to navigating one's own journey through young adulthood. (500) Days of Summer is why I cut my own bangs.

But the mess of the post-Y2K cultural landscape was as necessary as our dumb, youthful haircuts and our naive zest for wide-legged jeans worn with rubber flip-flops. Sure, so much of the era's TV, film and music felt incoherent and all over the place (much like anyone in their teens and 20s) — but, valuably, they helped set us up to create and consume darker, more complex art that led to bigger conversations and higher expectations. Tracing pop culture as it evolved through the 2000s right up to today, we can see how Tony Soprano led to Don Draper, who led to Eve Polastri, who led to Fleabag; Laguna Beach led to The Hills, which led to Keeping Up With the Kardashians, which led to Real Housewives and Vanderpump Rules. And frankly, the decade's lack of diversity in film was finally called out and (very, very slightly) corrected as the 2010s came to pass. (When I tried to think of which movies led to one another, all I could do was feel super bummed out about how so many of the 2000s' biggest films were targeted to sad, angry white men. Woof.)

While there were absolute gems to be found, the Y2K era was a shocking mess that reflected the discomfort most of us felt around the same time.- Anne T. Donahue

And of course, so much of the 2000s — the early 2000s in particular — felt caught in the midst of two eras because they were. When Friends premiered back in 1994, its storylines about six 20-somethings felt almost novel. But by its end in 2004, the series' plots were flailing: Chandler's digs about his trans father felt increasingly cruel and unnecessary (they always were, by the way), the show's lack of diversity was more and more painfully obvious, and Ross and Rachel's up and down relationship began feeling stale, as if the characters were immune to the type of rhetoric spawned by New York pals in the Sex and the City universe. (Like, say, you don't need to keep dating someone you've known since high school, Rachel.)

It certainly wasn't alone in its early-to-mid-aughts struggles. Gilmore Girls, while often adorable, is also built on whiteness and wealth and is in no way lacking in homophobia and fat-shaming. The West Wing, a beacon within the Sorkin canon, stans the type of white, God-fearing politician who represents the good old days — days in which the President would proudly stand up for right and wrong, but governs with a father-like presence, particularly over women. (Sorkin loves a father figure.) Meanwhile, the sexually liberated (or something) Gossip Girl opens its first episodes with an attempted rape scene at the hands of a character we're supposed to root for. Looking back now, much of the era's film and TV feels dated at best and deeply problematic at worst.

At the same time, there were moments that showed how culture was starting to shift for the better. Grey's Anatomy championed diversity and delivered important conversations about abortion, sexual assault and gender norms, to start. Erin Brockovich — a story that follows a woman's ascension to power and challenges classicism and elitism — is one of the greatest movies ever made, please and thank you. Even a silly, teen-centric rom-com like She's the Man used humour to explore the fluidity of sexuality and gender. Sometimes, the 2000s really did hit it out of the park — which was distracting enough to sometimes forget the Entourage universe was thriving elsewhere.

Ultimately, the 2000s were the growing pains that led to a decade that demanded work be sharper and better. And while there were absolute gems to be found — works like Arrested Development and The Wire, which we will cover in this column and I will totally gush about — the Y2K era was a shocking mess that reflected the discomfort most of us felt around the same time.

So naturally, like #TBT photos of my hair and fashion disasters, I'm psyched as hell for us all to start revisiting it as this column moves into a new decade. Or at least for me to finally have an excuse to listen to all 46 editions of The O.C. soundtrack.