Here are a few treasured memories from the late 1990s, in no particular order:
Being in college. While I didn't care for the stress of academic responsibilities, I did enjoy the much more flexible schedule. I could have a class in the morning, come back to my dorm for a couple hours for a leisurely lunch and some TV, attend 2 more classes, and be done for the day at 3:30. No cooking or cleaning. I miss playing Goldeneye on my suitemates' Nintendo 64 for hours on end. I never was very much into video games, but that one was addictive. I loved ordering pizza at midnight and watching "Unhappily Ever After" reruns with my suitemate. And I damn sure miss having 4 weeks off over Christmas and nearly 4 months off for summer. Only one of the 8 summer breaks during my college career did I actually hold down a job, where my co-worker and I goofed off and avoided real work as much as possible. The other summers were spent fucking around, watching TV, going to movies in the middle of a weekday, reading, drawing, creating, and doing basically what I'd do if I won the lottery and weren't chained to a day job, except it would be done in my own house and not living with my parents.
The extreme sports fad. I'm the last guy to participate in them, but the scene was cool to observe. Loud, up-tempo music, energetic graphics, and shameless product placement (Surge, anyone?).
The heyday of gimmicky chain restaurants. TGIFridays, Bennigans, O'Charley's, Chili's, Applebee's, etcetera were in full swing back then. The booming economy allowed the average Joe to eat out more often than nowadays, and chain restaurants sprang up all over the sprawling suburban wastelands across our republic to stuff his gut with deep-fried jalapenos, fried cheese, and potato skins. They're still around, but not in as strong numbers as 10 years ago. Apparently Bennigans has gone the way of the dodo. It's saddening. My friends and I used to go to gimmicky restaurants just for the experience of it, to soak in a bit of Generica.
Late '90s pop music. It was mostly mindless pablum and frat-tastic beats, with a smattering of meaningful stuff. Early Eminem, Limp Bizkit, Offspring, Britney Spears, Christina Whore-alera, and such, all reflected the blissful stupor of the late '90s. People were generally happy, the president was getting BJs left and right, and we celebrated with stupid, upbeat music.
Movies of 1999, some good, some so-so, some I got to see for free because a friend worked at a theater: Go, Never Been Kissed, The Mummy, Election, Star Wars Episode 1, Austin Powers, The General's Daughter, South Park, American Pie, The Blair Witch Project, Dick, The Sixth Sense, Fight Club, Dogma, Sleepy Hollow, Deuce Bigalow, The Green Mile, and The Talented Mr. Ripley. Analyze This, Big Daddy, Bowfinger, Mickey Blue Eyes, and Teaching Mrs. Tingle. I can proudly proclaim that I never saw Wild Wild West, not even on TV.
Automobile styling. I feel like it reached a peak sometime between 1998-2003. Most cars today are just plain ugly compared to their '90s predecessors (with the exception of the Chrysler 300). My '01 Toyota 4runner is much more elegantly styled than those that came a long in the mid-2000s. Ditto for Ford Explorers and Chevy Suburbans & Tahoes. I was overjoyed when Jeep Wranglers went back to circular headlights around 1998 from those stupid rectangular ones. Lines were streamed and curved, chrome was sparingly but elegantly employed. Today's cars seem to be going for more angular treatments, but not in a flattering manner, especially on the hideous hybrids one sees nowadays. A Prius looks like something Optimus Prime left in the john.
Kids' WB. Yes, I was legally an adult when this was on, but the cartoons were so much more awesome than the horseshit you find on children's programming nowadays. Batman: The Animated Series, Animaniacs, Pinky & The Brain, Tiny Toons, Sylvester & Tweety Mysteries, and Histeria were all great things to come back to the dorm and watch after classes.
Cartoons for grown-ups: King of the Hill, The Simpsons, Family Guy, The PJs, and Dilbert. I loved Dilbert. While I hadn't yet had the pleasure of toiling in a cubicle farm, I could nonetheless appreciate how well it must have spoken to those who spent a third of their weekdays languishing in gray cubes staring at computer monitors, as I do today. I guess some things don't change.
Dot-com startups. They were cropping up all over the place. Pets.com. Drugstore.com. Monster.com. Some survived, some died in the dust. But it was all so exciting! You never knew what cockamamie dot-com business was coming next. And every startup was seen as foolproof for investors. Never mind that most of them didn't have any strategy or business model and borrowed more money than they could ever pay back. It was the internet! It was a goldmine! Their offices were staffed by hip youngsters sporting soul patches and douchey orange-lensed eyewear, and had their own espresso machines! I long for those glorious days of the dot-com bubble. A company would come out of nowhere, announce an IPO, and Zoom! Its stock would shoot from a few bucks to over $100 a share the first day. Everyone got rich, at least on paper. The sky was the limit. The dot-com bubble burst in the spring of 2000, which is where I mark the beginning of the end of the glory days of the turn of the 21st century. Things were still OK overall. It remained OK after red-state mouthbreathers and crooked Floridian authorities got Dubya into the presidency. We were still naive; we didn't know yet that he'd become the worst president since Andrew Johnson and his vice-prez was actually Satan with a heart condition. For a time, he was just a goofy monkey-man with a speech impediment. 9/11/2001 is where I mark the end of my generation's gilded age. Everything went to shit from there. The USA-PATRIOT act pissed all over our civil liberties, Alan Jackson wrote that gay song, Ashcroft wrote an even gayer song and sang it in public, everyone got all serious, and the economy tanked, and never again got anywhere near the runaway levels of the late '90s.
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