1999 was Definitely the First Year of the 2000s

Let's take a look at how 1999 was different from the years before it.
October 26, 2020
Greetings and salutations Retrojunkers!

Is it odd to anyone else that stuff from the year 1999 gets mixed in pop culture from the 1990s? I am familiar with the Gregorian calendar like everyone else, but culturally, 1999 did not feel like a 90s year. The clothes, toys, movies, books, and tv shows of 1999 were all too modern to have appeared in the 80s or very early 90s. Living in 1999 was like living in a different world from now, the 2010s, and the very early 90s. Thankfully, 1999 was not too distant from the years 1997 and 1998.

(Will Smith in 1990)

(A teen in 1999 or 2000)

As you can see, the two pictures are worlds apart from one another. Playing a Nintendo Entertainment System would bore the 2000s teen and the 2000s teen would not have any idea what a CD long-box is. I bet Will Smith in 1990 would faint after hearing that a SONY PlayStation would be launched in 5 more years. The 2000s teen in that photo was an XYer and Will Smith is a member of Generation X. In 1999, I was into the same pop culture icons that that 2000s teen liked. The Bride of Chucky, H20 (the Halloween movie), The WB, early South Park, the New York Yankees, Kid Rock, Eminem, N'SYNC, Britney Spears, and Austin Powers were all on my radar. For that reason alone, I could never call 1999 a year of the 90s (I was old enough to tell the difference).

(90s culture born in the 80s)

(2000s culture was born in the 1990s)

The very early 2000s (1999-2001) were the most definitive part of the 2000s and it was the last time the world was anxious to turn on the radio or MTV before rushing out to buy the whole album from their favorite artists. There was some great music in the 2002 to 2004 era, also, but the songs released from 1999 to 2001 were so futuristic sounding that they are in a class of their own. There was a lot going on in the world in 1999. Gen Zers were beginning to watch TV, Late Millennials were starting elementary school, Core Millennials were on their way to middle school, Late XYers were teens, Early XYers were college students, and Late Gen Xers were producers for the first time. Despite all of that happening, 1999 will be most remembered for December 31 of that year as we were all afraid that none of us would live to see the year 2000 (the Y2K bug). In this article, I will be reviewing almost everything that happened in 1999 and how those things correlate with the rest of the 2000s.

The Clothes of 1999
Designer Clothes

In 1999, like any other time, there were different high school crowds who wore clothes that clashed with other cliques. The post-grunge fans wore Doc Martens, Mudd shoes, VANs, black JNCO clothing, and black bell-bottoms from Hot Topic. The hip-hop crew had bucket hats, MECCA tops, FUBU gear, and South Pole sweaters. The 'ghetto fabulous' movement was getting off the ground and you could not go anywhere in 1999 and the 2000s without seeing football jersey shirts, silky durags, and sagging pants. The preppie look was the mainstream look for many middle schoolers and young adults watched as GAP went up against Old Navy and Abercrombie and Fitch. At the time, there used to be a joke that GAP stood for 'Gay And Proud'. Some young adults were into 'the city scene' and they wore L.E.I. jeans, Paul Frank tees (as they were called then), and Sketchers sneakers. The mall was the hottest place to go to in those days because there were stores like dELiA*s, Wet Seal, The Limited, and Charlotte Russe still with us.

Our Wardrobes

As you can see from this photo, the overalls, stripe shirts, denim jackets, and fanny packs of the 1990s were gone. Anime (Japanese animation) and all things Japan was super popular that year. Pre-teens and teens were both tuning in to Toonami on Cartoon Network in the weekday afternoons for the earliest part of 1999 and the imports on FOX Kids every weekday and Saturday. Girls of this age were into fashion accessories like butterfly clips and chokers. After Columbine, teen girls had W.W.J.D. (What Would Jesus Do) bracelets on their wrists like they were Swatch watches in the late 80s. I think men's fashions stick out the most in 1999. We did the Hawaiian shirt with cargo shorts or Lee Pipes ensemble. Who could forget the Stone Cold Steve Austin and The Rock shirts? N.W.O. (New World Order) professional wrestling was big that year. Do you smell what The Rock is cooking?

Overall, clothing from 1999 is pretty simple to put together for guys - all you need is XXL jeans, a Hawaiian shirt, and a muted color shirt to wear underneath the Hawaiian shirt. Females can wear a tank top with dark denim jeans. I don't see the very early 2000s look coming back like fanny packs in 2019. Quite a few people in 1999 thought there would be spaceships and hoverboards in the year 2000, so our style reflected that. You would get laughed at today for wearing ski goggles or swim goggles on your forehead as young men did in the late 90s and very early 2000s. So, the clothing of 1999 (The Y2K aesthetic) is stuck in the 2000s for possibly all of eternity.

The Music of 1999

There was a lot of variety in music in the same year that brought us "No Scrubs" by TLC and "Believe" by Cher. Rock fans were obsessed with the urban legend that Marilyn Manson was really Josh Saviano when they were putting down their Korn, MuDvAyNe, Slipknot, and Disturbed CDs. The music world of 1999 is best remembered for the Latin explosion that erupted that year. There was Jennifer Lopez, Marc Anthony, Enrique Inglesias, and Ricky Martin to feel sexy and confident when in the presence of your loved one. 1999 was, also, the biggest year for teen pop in all of history. Britney Spears, *NSYNC, and the Backstreet Boys already had hits in the late 90s, but newcomers like Mandy Moore and Christina Aguilera were giving them all good competition. I thought Christina Aguilera was a hottie at the time because she had blonde hair, eyes you could get lost in, a soulful voice, and the whole genie in a bottle getup(do what you want with me). Britney Spears had a much larger Generation Y following in those days, but as you can see, Christina Aguilera has gone nowhere (her name is out there far more than Britney's).

One of the coolest punk rock bands at the time was Blink-182. I can attest to turning on MTV TRL to watch the video for "All the Small Things". I still know all of the words to that song. I avoided music by Smash Mouth and Limp Bizkit in 1999. I did know people who took Limp Bizkit seriously then, but I saw Fred Durst like parents saw Vanilla Ice in 1991 (a flash in the pan). Both Blink-182 and Slim Shady (Eminem) had unironically hilarious music videos, so I could get behind them. Around 1999, my generation was even bleaching their hair with Kool Air and Bleach to get the Slim Shady look down. Parents were disturbed by the lyrics to some of Slim Shady's songs which meant that teens and pre-teens had to hide their albums.

Girls in 1999 wanted to form their own groups like Destiny's Child. "Bills, Bills, Bills" and "Bug A Boo" were the contemporary R&B hits that girls all across the US were singing along to (especially "Bills, Bills, Bills"). No one in 1999 knew that all four of the members of Destiny's Child would go solo in the 2000s. The Writing's On The Wall was the album that quite a few people were making using Napster. "Bills, Bills, Bills" peaked at number 1 on the Billboard Hot 100 charts on July 17, 1999 in the USA. Sadly, Destiny's Child was not quite on our radars that year like the Backstreet Boys and *NSYNC.

Some guys in 1999 were lip-syncing the Backstreet Boys and *NSYNC, in the same way, the pre-teens of 1989 were doing it to New Kids on the Block and Milli Vanilli. The music video to "I Want It That Way" was so over the top that young men couldn't help but laugh at it. *NSYNC obviously won the late 90s and early 2000s war between them and Backstreet Boys (Justin Timberlake's career speaks for itself), but I think Millennials have the most nostalgia for Backstreet Boys songs. At the time, it felt like *NSYNC was piggybacking on the success of the Backstreet Boys. The sound of the singles by both groups was miles ahead of what you heard from boy bands in the 90s like New Kids on the Block and Take That. I must say that the *NSYNC albums are not dated like Backstreet's Back or Millennium. All of this talk about the music of 1999 reminds me of MP3s which brings me to...

The Websites of '99

Everybody's favorite activity in 1999 was to surf the web with our dial-up internet. The world wide web in 1999 was the television set in 1960. When you think about it, 1999 is not too distant from today - we still use Yahoo, Google, and AOL as our search engines. Unlike today, there was a lot of file sharing (digital music piracy) and you could not listen to MP3s without downloading them. Napster was the most controversial website in 1999 because Gen Xers, XYers, and younger Millennials were collecting mp3s of the singles they were not buying to make mix CDs with. All of this was being done after school (a long way from when my generation would watch weekday afternoon cartoons). After a while, my generation and generation before me were afraid of being put in jail for having music files on our computers.

There are some other sites that were with us in 1999 that are gone today. Ask Jeeves seemed like the smarter alternative to the big 3 (Yahoo, Google, and AOL) in 1999. I would type in actual workplace-related questions for Jeeves to answer. When that went nowhere, I would go to Lycos.com and play online games or go on Shockwave.com to watch online videos. The homemade websites on Angelfire and Tripod (free and paid for sites) were my favorites to look at because those sites had the most information related to the pop culture of the time. I would even sign my name in the guest books sometimes or check out the sites listed as part of the webring.

You could not be alive in 1999 and not have a free America Online CD. I would pop in the CDs whenever I could not log in to my AOL account or the account had expired. Sometimes, I would talk to my friends using AIM (AOL Instant Messenger), and other times I would take a walk on the wild side and go into a chatroom. I remember parents telling their children not to go into the chatrooms because there was a chance that they could be talking to a grown person (this was before To Catch a Predator on Dateline NBC). I do remember flirting with [possibly] a few women from different parts of the US using the AOL chatroom, but those people never returned to the chatroom. You had to enter the chatroom at different times of the day to meet with some people. Thankfully, the AOL chatroom fad did not last too long into the 2000s (it was aggravating sometimes).

Children had many reasons to visit the net in 1999. Both girls and boys went to The Doll Palace to make Dollz of themselves and original characters from their stories. I recall my niece saying that she had to be careful copying Dollz from homemade websites because the owner of the Dollz could take them off the page that my niece built. Then, MySpace and other social media websites came along, children started taking selfies of themselves, and The Doll Palace was history. Those same children were going to websites like Amazon and eToys to purchase stuff like the latest Gameboy Pokémon games, inflatable chairs, and Pixar collectibles. It's funny that Toys "R" Us bought eToys when online sites like Amazon and eBay put TRU out of business 2 years ago. In the spring of 1999, Pokémon was larger than life and the Internet...

Pokémon Memorabilia of 1999

Pokémania was the largest craze of 1999 into 2000. Millennials used to go to Borders Bookstore to compare the strategy guide of Pokémon Red and Blue or Pokémon Yellow to the tips found in Nintendo Power magazine. Other Millennials wanted to cosplay (costume play) as Ash Ketchum and it was the costume that was easy to put together - all you needed was a Hasbro Talking Pokédex game, officially licensed Nintendo Pokémon League Expo hat, and a DIY (Do It Yourself) jacket, gloves, shirt, jeans, and sneakers. The most controversial Pokémon items were the Hasbro Pokémon Power Bouncers balls because a few small children passed away from choking on them (most likely trying to get the little Pokémon out of them). There were Pokémon bed sheets, PVCs, shirts, plush dolls (at the arcades as well as stores), VHS tapes, DVDs, watches, stickers, knock-offs (Digimon), and even books in the year 2000 about collecting Pokémon merchandise.

Millennials all had Pokémon Pikachu virtual cyber pets in the summer along with Pokémon Pinball for their GameBoy Colors and the Pokémon The First Movie Burger King Big Kids meal toys. I knew Pokémon made it in the US when the characters came in the Burger King kids' meals and value meals. The Big Kids meal toys came in Pokéballs and blind bags, therefore it was hard to discern which character you were getting. This made it a mess for parents who wanted to get all 57 characters for their Millennials. Some have argued that the best Pokémon were missing from the set, but it still remains as one of the Millennials' favorite Burger King toy collections. The biggest missed opportunity for these Big Kids meal toys was no TCG (Trading Card Games) coming with them.

Toys of 1999

Many Millennials confuse 1999 for being a late 90s year because their tastes were not that different from how they were in 1997 and 1998. 1999 was its own time and a minuscule amount of the new pop culture from the late 90s was starting to go downhill. The Pokémon Trading Card Game and Furby were the standouts in the schoolyards and playgrounds in 1999. Adults trying to score holographic Pokémon cards for their children or nieces and nephews would say that the Trading Card Game was not even a Trading Card game because Millennials were not willing to give up their most prized possessions for four or more common and uncommon cards (the Pokémon TCG cards weren't baseball cards). Regardless, children were trading Pokémon cards everywhere from the church to camp. Between closing our ears whenever a Furby was around and children missing in American Pokémon trading cards with Japanese trading cards, not too much was going on.

Both Pokémon and Nick Jr.'s Blues Clues have staying power, but no one knew that back then. Both properties will never be as big as they were when they were somewhat new. The Pokémon Trading Card Game put all Trading Card Games and Japanese Animation on the map. The Pokémon Trading Card Game booster packs and Blue Clues dolls were sold out for a while in '99 until stores everywhere ordered lots of them. There were Japanese vendors in the mall with the latest Pokémon Trading Card Game booster packs and themed deck. It's amazing that no child at the time thought to save up their cash and buy a box or two of the latest Pokémon Trading Card Game booster packs or stroke the booster packs with their fingers to feel for the rare holographic cards.

The Tech Deck fad never took off like the Pokémon TCG, but it succeeded in bringing people who did not board into skateboarding shops in the mall. Beanie Babies and Giga Pets were still a hit with children and adults. Meanwhile, the Transformers Beast Wars crowd was ignoring the Animorphs toys at KB Toys. Movie toys like Star Wars Episode 1 and Austin Powers The Spy Who Shagged Me toys flew off shelves the minute they were unloaded from the trucks onto the store shelves. I thought the Hasbro Star Wars Commtech approach would last well into this new Millennium, but the idea was thought up in the late 90s and discarded in the Bush 2000s.

The Video Games of 1999

1999 was a great year for video games. The SEGA Dreamcast was sold in North America, Millennials were playing Pokémon SNAP at Blockbuster, and parents were relieved that Macy's, McDonald's, and Bloomingdales all had N64s kiosks. Millennials were still playing Metal Gear Solid for PlayStation at the beginning of '99, but they would soon take that out for their Silent Hill and GTA2 games to load. I could never play Silent Hill because that game was scarier than anything Clive Barker or Stephen King could have thought of. GTA2, on the other hand, seemed boring to me because you were only carjacking people (give me Vice City or San Andreas).

Tony Hawk's Pro Skater was one of the best games for PlayStation in 1999 because you could perform skateboard tricks as Tony Hawk or any other top skater of the nine professional skaters to punk rock and ska music. It was very much a product of its time. There was a demo of the game on the Playstation compilation disc given away at Pizza Hut that fall. Pikachu was the face of video games in 1999. There was
Pokémon Pinball, Pokémon Yellow, Pokémon Snap, and Super SMASH Brothers.

Pokémon Snap was fun because you went to different locations to find most of the 150 Pokémon. It was a little bit like Pokémon GO, but you could sit on your couch and take snapshots of the pocket monsters. Super Smash Brothers was the game of the year and you could battle all of the Nintendo game mascots as your favorite main protagonist from a Nintendo game. It is my belief that the game sold so well because you could pit Pikachu, the then-latest Nintendo character, against Mario, from a video game franchise that everyone is familiar with. I never got around to playing Super Smash Brothers, but I remember seeing boys play it at EB Games and Funcoland.

TV Shows We Were All Watching in 1999

Women in 1999 were swooning after seeing George Clooney in ER, children were catching Pokémon [no pun intended] on Kids WB, and teens were watching Must See TV (Frasier and F.R.I.E.N.D.S.) on NBC. 1999 was the first time in years that a game show (Who Wants To Be A Millionaire?) went to number one in the Nielsen rating chart. There was something so lovable about the late Regis Philbin as the host that casual viewers tuned in to see if the contestant was going to answer all of the questions correctly. After Who Wants To Be A Millionaire? came out, almost everyone was throwing around the word 'lifeline' at the offices and schools.

Monday nights were reserved for Monday Night Football and Wednesday nights were Law and Order nights (a tradition that went on until late 2010). I could never understand the jargon that Frasier or Niles Crane (Frasier’s brother) used, so that wasn’t on much in my living room. There were too many breakout stars on Everybody Loves Raymond from Brad Garrett to Peter Boyle. I barely remember any quotes from Ray Barone, but I was jealous that he was married to Debra played by Patricia Heaton. It was a coincidence for me that Touched By Angel aired on Sunday nights on CBS. It was nice to have a drama that wasn’t a crime drama and some light comedy that did not come from Chandler or Joey.

TV Show Premieres of 1999

The TV show debuts of 1999 further illustrate my point of how 1999 was the turn of the new century. Several shows that first aired in that year were shows we could not live without in the very early 2010s (Spongebob Squarepants, Judge Mathis, and Family Guy). Some tv pilots were continuations to the shows introduced in the 90s (UPN's The Parkers and NBC's Law and Order Special Victims Unit), while others were hoping on the latest trends of the time (MTV Undressed). There was, also, a neo-adult primetime cartoon revolution in 1999 with programs like Futurama, Family Guy, and Mission Hill (all thanks to the popularity of The Simpsons, South Park, and King of the Hill). Not too many of my friends were watching the first season of Family Guy (probably why it got canceled in 2001), but I taped Futurama and watched it whenever I had the chance to.

HBO's The Sopranos, much like Game of Thrones in 2011, was all everyone was talking about shortly after it aired. All of the office talks went over my head because I did not have any of the movie channels at the time. Freaks and Geeks on NBC was the greatest TV drama to me because children of the 80s (like me) finally had another period piece set in the 80s. I liked That 70s Show too, but the writers did not set the show in the early 70s when the 70s were alive (I felt cheated). Unfortunately, all of the best new basic cable shows of that era like Freaks and Geeks were getting canceled time and time again. I guess the saying goes that the Internet killed the TV star since people were doing as much research using the world wide web as they could in those days over watching the tube (it was a new time, but most of the world didn't know it).

The Movies of '99

The multiplex was the place to be in 1999. Oddly enough, I heard nothing about Fight Club until 2003 or 2004, but I probably would have seen Fight Club as an action movie. There were more epic film series and raunchy teen films coming out in 1999 than anything else. There was a lot of hype for Star Wars Episode 1 because it was the first Star Wars film made in recent times. Children of the 70s and 80s thought it would be up there with the classic trilogy. Now, no one mentions it when bringing up 1999 because there were better films for children (Toy Story 2) and sci-fi fans (The Matrix).

Seeing Cowboy Curtis (Lawrence Fishbourne) without hair starring alongside Ted Logan (Keanu Reeves) was a huge eye-opener. The Sixth Sense might have made Haley Joel Osment into a huge child star, but The Matrix was the era-defining movie because of its predictions for the internet in the future. At the time, I made the foolish mistake of thinking that there were two American Pie[/i] movie - American Pie and American Beauty (both had Mena Suvari in them). American Pie got more acclaim from teens at the time while the writers, production team, and actors of American Beauty were taking home more awards. Although they were not allowed to see it, She's All That was popular with Millennials who read about it in J-14, Seventeen, and YM.

Office Space based on the Milton sketched by Mike Judge is my all-time favorite movie of 1999. It had everything from Jennifer Aniston to references to the singer Michael Bolton to catchphrases from Bill Lumbergh. I felt for Milton as Bill Lumbergh gave him more and more tasks to complete. I watched Office Space on Comedy Central many years after it was in theaters and the only question I had was, "Is this Milton's movie or Peter Gibbon's film?" Peter Gibbons was in the best scene of the film which was the smashing of the office printer that the guys hated. The filmmakers of 1999 helped quell the unrest we had after looking at the news in that year...

Important Events of 1999

TIME magazine called the 2000s "the decade from Hell". Technically, the 2000s were not a decade, but they were still a scary time to live in from Columbine to 9/11 to Hurricane Katrina. I don't know where I was when the Columbine High School Massacre happened, but the made for TV movies about what occurred is coming back to me as I type this. There were certainly a lot more metal detectors in school after the school shooting and attempted bombing happened. Luckily, Americans had funny phrases to use to take their mind off of the negative moment.

Bill Clinton was acquitted in '99, so lots of males were saying, "I did not have sexual relations with that woman." When those males didn't say that, they were singing the jingle to Chili's Baby Back Ribs (a la Fat B*$t@rd). Austin Powers The Spy Who Shagged Me had so many memorable lines in it from Doctor Evil, Austin Powers, and Fat B*$t@rd alone. DVDs were outselling VHS tapes for the first time, so times were changing and we needed something to laugh at to get through it all.

When it comes to 1999, I remember not wanting to be around a COMP USA or Circuit City in fear of the computers exploding on 12/31/99. The world was 'waving their hands to the 1900s' (we didn't know we were already in the 00s) as computers were taking over right before our very eyes. With that said, people were still lining up to own the Mac iBook like the iPod and iPhone. The iBook was sleek with fun colors in a white box that looked like it came from what we thought the year 2015 woulk be like. I recall seeing the empty iBook boxes on many sidewalks in places like New York City in 1999, 2000, 2001, 2002, and 2003 whenever I went on vacation. It really felt like we were in a different world from that of 1991 or even 1996.

The Wrap Up

Being in my 20s in '99, I feel that I didn't enjoy the year 1999 in the same way that a Core Millennial, Late Millennial, or Early Gen Zer would. I know there was more to the year that what I listed here like the hacking of the Hotmail accounts, Michael Jordan retiring, Ryde or Die Vol.1 being sold at Sam Goody, The Mummy, the Euro coming to world financial markets, and the Harry Potter and the Prisoner of Azkaban Midnight Release Party at Barnes and Noble, but I did not experience it. The most I know about '99 was that children were robbing children of expensive First Edition Pokémon cards and that Pokémon was everywhere (Japanese stickers were in the prism sticker machines at A&P grocery store even). I had a hard time adapting to the 21st century world that started in 1999 because my favorite 20th century functions were becoming passé. Fortunately, 1999 had more spark in it than today does. I refuse to see 1999 as a late 90s year, but it was closer in tone to the late 90s than 2009 or 2017 (I'll give it that).

You can find more information on 1999 in this month's issue of Remind magazine. Here is a picture of the cover and a sneak preview of the Time Capsule article on '99.

You can usually find small articles on Buzzfeed about 1999. For example, here is one:


The best article I have found was IGN Presents the History of Awesome for 1999. I believe there is a video somewhere on IGN for 1999, but I cannot find it at the moment.


There will always be information available on different sides on the year 1999 online. To me, 1999 is one of the most important markers on the timeline because it separates this time from the ages before 1999.

Well, it was nice revisiting my memories of 1999 for you, RetroJunkers, but I have to go. I hope this article helped refresh your thoughts on 1999, so you can type an even better article than this one. Until then, best of wishes to you all!

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