What was going on in the world in the lead-up to Y2K

In the era of Spotify, it’s hard to articulate what a game changer Napster was. Sure, it wasn’t legal. In hindsight, Lars Ulrich was right that it kind of sucked how artists were losing money to people downloading music for free. Also, seemingly half the songs you downloaded had been mislabeled. On the other hand…we were able to download music! On the internet!

The Academy Awards event that happened in early 1999 was, of course, the night the movies of 1998 were handed out. Many expected Steven Spielberg’s “Saving Private Ryan” would win Best Picture, and Spielberg did win Best Director. However, “Shakespeare in Love” pulled off the Best Picture upset. It is the prevailing narrative that “Shakespeare in Love” won thanks to the politicking and campaigning of…well, let’s just say a certain future convicted felon who made his name in the film industry.

The 2024 college football season offered us the first 12-team playoffs. We’ve come a long way since the 1998 campaign. This was the first year of the Bowl Championship Series, or BCS. If you’re too young to remember the BCS, well, it involved computers and made seemingly everybody angry. The first BCS-fueled title game occurred January 4, 1999 in the Fiesta Bowl. There, the Tennessee Volunteers beat the Florida State Seminoles 23-16.

For many years, Canada had 10 provinces and two territories. While the country still has 10 provinces, in 1999 the number of provinces rose. A portion of the Northwest Territories was carved out to make way for Nunavut. It is self-governed by the Inuit, who have been in that region for centuries.

The Woodstock event of 1999 is well-trodden territory by now. In the time it took us to type that sentence, another three documentaries on Woodstock 1999 dropped. It was not a chill time for music, not an event of peace, love, and understanding. No, it was rife with price gouging, unsanitary conditions (okay, that’s the same as the first Woodstock), and violence. Also, a bunch of bands that were awful played.

Old money and family fame have their perks. The son of former President John F. Kennedy (duh), JFK Jr. was a gadabout, a Manhattan playboy, and a “Seinfeld” joke. Be that as it may, it was still unfortunate, and huge news, when Kennedy Jr. died in a light aircraft accident at the age of 38. 

In 1999, the third FIFA Women’s World Cup occurred, and this was the one where the event really took off. It helped that it was being held in the United States, and that the U.S. made it to the final against China. The game went to penalty kicks, and Brandi Chastain was the fifth shooter for the U.S. If she converted, the USA would win. Chastain indeed scored, and then in celebration tore off her shirt and unveiled the most-famous sports bra in history.

After the fall of the Soviet Union, Russia did something it had never done before: Elected a president. Boris Yeltsin won the first presidential election in 1991, and the oft-lampooned figure stayed in the role until 1999. He was not terribly popular in Russia, which may have played a role in the election of a self-described strongman with ties to the Soviet Union’s “glory days” as it were: Some guy named Vladimir Putin.

At this point, the word blog feels almost quaint. It’s probably the fault of “Juno.” The idea of a blog being a portmanteau of “web” and “log” is essentially no longer thought about, unlike the word podcast, which is no longer tied mentally to the iPod. Back in 1999, though, “blog” was a brand-new coinage.

Infamously, Art Modell took the famed, beloved Cleveland Browns away from the city and took the franchise to Baltimore in 1996 where it became the Ravens. The NFL didn’t block the move, but they knew that Cleveland should not be left without professional football. Thus, the league swiftly moved to not only give the city an expansion team to begin play in 1999, but when the Browns returned, they were given all of their history back, with Ravens history only beginning in 1996.

Elway is a Broncos icon, and one of the best quarterbacks of all-time. Sanders is one of the best running backs of all-time, and was one of the only bright spots for the Lions franchise for many years. Both retired in 1999, but under different circumstances. Elway led the Broncos to the second of two Super Bowls in a row and retired on top with the entire city of Denver behind him. Meanwhile, with the career rushing record in sight, Sanders surprised Lions fans, and the Lions franchise, by deciding to retire while still playing high-level football. It would be years until Sanders and the Lions patched things up.

The Rams went 4-12 in 1998, and while they had added Marshall Faulk from the Colts, disaster struck when starting quarterback Trent Green tore his ACL in a preseason game. Head coach Dick Vermeil said the Rams would rally around new starting quarterback Kurt Warner, but Warner was 28, had never started an NFL game, and played the 1998 season in NFL Europe. Well, St. Louis went 13-3, Faulk won Offensive Player of the Year, Warner won MVP, and in early 2000 the team would win the Super Bowl.

Young folks, back in the days the Dodgers weren’t the franchise that frustrated 29 fan bases with big spending and a ton of success. No, the New York Yankees were the “Evil Empire.” While the Yankees have not won a World Series since 2009, they won in 1996, 1998, and then in 1999 dropped all of one game en route to another title. Oh, and then they would win in 2000 as well.

Here’s a good way to chronicle the passage of time. Beltran retired in 2017. He’s best remembered for his role in the Astros’ sign-stealing scandal, which led to him resigning as Mets manager in 2020. Well, back in 1999 he was a rookie with the Kansas City Royals en route to winning Rookie of the Year. The National League winner was, um, relief pitcher Scott Williamson.

The 1998-99 NBA season was, technically, the 1999 NBA season. Team owners, hoping to put a hard cap on individual player salaries, locked out the players. The lockout would push the start of the season to February 5, 1999, and limit it to only 50 games.

Famously, Michael Jordan retired after winning three titles with the Bulls but did not stay retired. He returned and won titles in 1996, 1997, and 1998. Then, while the NBA was locked out, Jordan announced he was retiring again in January of 1999. Of course, he would un-retire again and play for the Washington Wizards in the early 2000s.

You may know the Spurs as a highly-successful franchise with several titles. That wasn’t always the case. When the 1998-99 season began, the Spurs had zero titles and Tim Duncan was early in his career. Duncan and David Robinson joined forces to win the franchise’s first title in 1999. By the way, the Spurs beat the Knicks, which is notable because they were the eighth seed in the Eastern Conference.

Carter is in the Hall of Fame. He recently just became the first Raptors player to have his number retired. Part of Carter’s Hall resume was built on the fact he played 22 seasons in the NBA, leaving multiple generations familiar with the game of “Vinsanity.” He had to start somewhere, though, and the 1998-99 season was Carter’s rookie year. He averaged 18.3 points per game with the Raptors and won Rookie of the Year.

In the 1998-99 Stanley Cup final, the Dallas Stars faced off with the Buffalo Sabres. Neither franchise had a title. Buffalo was led by the legendary Dominik Hasek in net. Game 6 went into triple-overtime. Hull, an all-time goal scorer, scored what ended up the clinching goal. However, his skate was in the crease, and according to NHL rules at the time that arguably meant it shouldn’t have counted. It did, but don’t mention that to Buffalo sports fans.

For decades, the NHL had handed out the Art Ross trophy for the most points in a season. What about the guys who light the lamp, though? For the 1998-99 season, the NHL debuted the Maurice “Rocket” Richard trophy. Named for the legendary Canadien, the trophy goes to the player with the most goals in the season. The inaugural winner was Teemu Selanne, who scored 49 goals for the Mighty Ducks of Anaheim.

The ageless Jagr simply won’t retire, and that’s kept him out of the Hall of Fame. He was still going strong in the NHL at the turn of the millennium, though. Jagr tallied 127 points for the Penguins in the 1998-99 season to win the Art Ross. That was the second win out of four wins in a row.

Gretzky played 70 games for the New York Rangers in the 1998-99 season. He had nine goals and 53 assists. Perhaps the man who wore the number 99 saw some fitting symmetry in hanging up his skates in 1999. Gretzky retired at the end of the 1998-99 campaign, and the NHL retired the number 99 across the league in early 2000.

If you happened to opt for the Comets as your WNBA team when the league began play, you got lucky. Houston won the first four WNBA titles. In 1999 the Comets beat the New York Liberty for their third championship in a row. Speaking of the march of time, the Houston Comets ceased operations in 2008.

The only hyped boxing match of the last decade or so featured a YouTube star squaring off with a man in his fifties. Back in the day, though, boxing matches could still be quite hyped, and there were famous boxers. The fight of the year is one thing, but one bout was billed as “The Fight of the Millennium.” Felix Trinidad was 35-0 and the IBF welterweight champion. Oscar De La Hoya was 31-0 and the WBC welterweight champion. The fight went 12 rounds, one judge declared it a draw, while the other two gave Trinidad the slim victory.

Woods was a golf superstar in 1999. He only won one major, the PGA Championship, but he was a force on the tour. Tiger won eight tournaments, was the money leader, and was named Golfer of the Year. That summer Payne Stewart won his second U.S. Open, but tragedy would soon follow. In October, Stewart died in a plane crash.

In 1999, Steffi Graf won her 22nd Grand Slam tournament. This was the record…for many years. That same season Serena Williams won the U.S. Open, her first Grand Slam. It would be her first of 23 Grand Slams, which became the new record…ish. Margaret Court did win 24 Grand Slams, but 11 of them were Australian Opens in the 1960s and 1970s, and Court was Australian. Back then, it wasn’t feasible for a lot of top tennis players to get to Australia for the tournament, so Court’s 24 titles come with an asterisk to some.

In 1999, men’s tennis was not quite primed for its changing of the guard. Roger Federer would not win his first Grand Slam until 2003. Instead, a couple of icons nearing the end but not quite there were still the top forces in men’s tennis. Sampras won Wimbledon, his 12th Grand Slam title. Agassi, meanwhile, won both the French and US Opens.

Alright, let’s move past sports. Obviously, sporting events are one of the best ways to create a time capsule, but movies are good for that as well. These days, we have spent years inundated with “Star Wars” projects both on the big screen and small screen. In 1999, though, things were different. “Star Wars: Episode I – The Phantom Menace” was the first new “Star Wars” movie since “Return of the Jedi” in 1983. The excitement was massive, and the prequel was a huge commercial success. That’s impressive, given that, you know, it’s not a good movie.

“The Matrix” arrived at the right time. Its quasi-futuristic nature made a lot of sense with the new millennium around the corner. The CGI, particularly the “bullet time” slo-mo scenes, really grabbed people. Sure, the sequels are all mediocre at best. Yes, when you revisit “The Matrix” the plot makes zero sense. At the time, the style completely hid the substance and took the world by storm.

Shyamalan was a punchline for so long that, “Actually, he’s a really good director” is not even an interesting bit of contrarianism. That’s well-worn at this point as well. Why did Shyamalan even become a household name worth having an opinion on in the first place? That all started with “The Sixth Sense.” The film was a massive hit and a critical darling, and it made child actor Haley Joel Osment a known quantity. Now, personally we don’t even think “The Sixth Sense” is a good movie, but we don’t need to get the Shyamalan backers all riled up. They’ll tell you “Old” was good, much less “The Sixth Sense.”

You know, the days of watching movies over and over on Comedy Central are so passé, “Office Space” may not even be part of the cultural wallpaper if you are young enough. In 1999, Mike Judge was riding high on “Beavis and Butt-Head” and “King of the Hill” and was given the chance to direct a live-action comedy. “Office Space” is from a world before cell phones or widespread use of the internet or Jennifer Aniston being a movie star. It wouldn’t be a hit at the time, though. No, once it arrived on VHS (and a new-ish technology called DVD) and, yes, debuted on Comedy Central, things would start to turn around.

Imagine the “Blair Witch Project” cultural cycle playing out in the world of social media. The film, which reshaped the idea of “found footage horror” took advantage of the burgeoning internet, but also the limitations of the internet in 1999. It was posited this was real footage, and the actors involved (all unknowns) real people. Sure, the sensible minded knew no forest boogen had killed those filmmakers, but what was real here? In 1999, that was much harder to parse.

“American Pie” was indicative of the comedy landscape in 1999. Of course, that includes the fact a comedy movie could, you know, be a hit and spawn sequels. Eugene Levy was known to comedy lovers, and Jennifer Coolidge was maybe remembered for that one “Seinfeld” she was in. In 1999, though, she was “Stifler’s Mom.” Levy was “Jim’s Dad.” Pies were defiled. We used to build things in this country.

Were you confused by the Brendan Fraser renaissance? Well then you probably aren’t an Elder Millennial. The year 1999 was huge for Fraser, who emerged as a movie star in a major way. In “Jim Carrey in 1994” mode, Fraser starred in three movies: “Blast from the Past,” “The Mummy,” and “Dudley Do-Right.” Sure, none of those movies are good, but there are a lot of Elder Millennials who will try and convince you “The Mummy” is a classic.

We could do a lot of “This celebrity died in 1999,” but one death felt like a changing of the guard. Back in the day, Gene Siskel and Roger Ebert were tastemakers. They were highly-respected film critics and movie thinkers. They had a hit TV show. On February 3, 1999 Siskel told fans he was taking a hiatus from the show, but would be back as soon as possible. What nobody outside his family knew was that Siskel had been dealing with brain cancer for a few months, and on February 20, 1999 one half of the most-famous critic duo in history passed away at the age of 53.

Jon Stewart was not a news guy. He was not a politics guy. He was a comedian and sometimes actor who did stuff on MTV. When Craig Kilborn’s time as host of “The Daily Show” came to an end, Stewart was tapped to host. At the time, “The Daily Show” was much less political and more a parody of magazine programs. It was during the run up to the 2000 election things would change.

First, remember when it was WWF, not WWE? The then-WWF had Monday Night Raw going for many years, and had been in a head-to-head battle with WCW’s Monday Night Nitro. Finally, WWF added another primetime show, which had a name borrowed from The Rock’s catchphrase. Also, remember when Dwayne Johnson was solely known as The Rock?

Elway, who we previously mentioned, led the Broncos to a win over the Atlanta Falcons in Super Bowl XXXIII. That paved the way for FOX’s lead-out programs. After all, why not use the Super Bowl to goose the ratings of one of your shows? While a Super Bowl-themed “Simpsons” aired that night, first we got the premiere episode of “Family Guy,” FOX’s other defining animated series.

Look, we’ll just throw out some names, because a lot of significant TV shows first hit the airwaves in 1999. “The Sopranos” and “SpongeBob SquarePants,” for example. Those are the shows with the biggest cultural impact, but there was also “Futurama,” “Who Wants to Be a Millionaire,” “Law & Order: Special Victims Unit,” “The West Wing,” “Freaks and Geeks,” and, of course, “Shasta McNasty.”

In terms of inflow and outflow, 1999 was a net positive for TV (“Shasta McNasty” aside). Only a handful of shows of note called it a day in 1999. Apologies to the “Brimstone” diehards out there. Sadly, “NewsRadio” came to an end, as the show never recovered from the shocking murder of star Phil Hartman. “Home Improvement,” “The Wayans Bros.,” and “Melrose Place” all ended. So did “Mystery Science Theater 3000,” though of course it would return.

Back when streaming wasn’t a thing and if you wanted to watch TV shows you pretty much needed cable (or a satellite dish), new channels would be added on occasion. Nickelodeon brought two new networks into existence in 1999. Noggin was basically Nick Jr. the network, while Nickelodeon Games and Sports for Kids (or Nick GAS) was basically a clearinghouse for reruns of old Nick game shows.

The 1999 Primetime Emmy Awards were hosted by, of all people, Jenna Elfman and David Hyde Pierce. That made it convenient for Pierce when, yet again, he won Outstanding Supporting Actor in a Comedy Series for playing Niles Crane on “Frasier.” While “Ally McBeal” won for Comedy Series, “3rd Rock from the Sun” won for both Lead Actor (John Lithgow) and Supporting Actress (Kristen Johnson). Ultimately, “The Practice” had the best day. The show won three Emmys, with no other winning more than two. The drama won for Supporting Actor, Supporting Actress, and Drama Series.

There were some excellent “oh-so 1999” pairings of host and musical guest at the turn of the year in the middle of the 24th season of “Saturday Night Live.” Sarah Michelle Gellar and the Backstreet Boys, for example, though they both had some legs (some!). On January 16, 1999, though, Dawson himself, James Van Der Beek, was the host, and former House of Pain member Everlast was the musical guest.

The 25th season of “SNL” kicked off with two timeless guys in host Jerry Seinfeld and musical guest David Bowie. This was a notable year for the show, though. Two popular cast members joined the show as featured players. Those would be, as you likely surmised, Dratch and Rudolph.

Pop had a moment in 1999. Britney Spears and NSYNC were among those who entered the fray. MTV brought “Total Request Live” to the masses. Teenagers in New York City would screech into microphones over their favorite pop stars. While the ebbs and flows for these pop stars would make many a head spin, these were glorious dads for teenybopper pop.

The biggest hit single of 1999? Spears’ “…Baby One More Time.” That’s no surprise. Number two, though, may surprise you. Lou Bega’s one-hit wonder “Mambo No. 5” was that big of a hit. Now, there may be an easy way to track the reasoning. Bega was German by extraction, and so perhaps he was able to tap into the European market for sales purposes. Indeed, the song never rose above number-three on the Billboard charts in America, but hit number-one all over his home continent.

How about the top albums, what with albums still being the way music was sold (remember, Napster only debuted in 1999). Outside the aforementioned pop superstars, in the top 10 albums of the year we find Twain’s “Come On Over” (a pop-country classic), Martin’s self-titled album featuring “Livin’ la Vida Loca,” and, um, Kid Rock’s “Devil Without a Cause.”

Why were people fascinated by Hill for so many years as she continued to not deliver any new music or show any ability to be reliable professionally? Because 1999 happened. “The Miseducation of Lauryn Hill” dropped in August, 1998 and was the preeminent force at the 1999 Grammys. Hill received 10 nominations, and she won five Grammys. In addition to winning Best New Artist, “The Miseducation of Lauryn Hill” became the first hip-hop album to win Album of the Year.

The Nintendo 64 and the Sony PlayStation were already in the mix. In 1999, Sega got back into the console wars. The company fell a little behind, but dropped the Dreamcast in Japan in 1998 and brought it to North America in 1999. While it was behind the N64 and PlayStation, it got to the market before the Gamecube and PS2. Alas, it was not meant to be for Sega. The Dreamcast was a flop, it was discontinued in 2001, and Sega got out of the console game.

Cue up the Goldfinger! “Tony Hawk’s Pro Skater” dropped in 1999 and it ruled. The game was a huge hit that spawned a franchise. It helped turn Hawk not just into the first skateboarder celebrity, but the first skateboarder mogul. In fact, all these years later, nothing in the skateboard game space can touch the “Tony Hawk’s Pro Skater” franchise.

No, Pokemon did not debut in 1999, but you could not escape those pocket monsters in the video game space. Two of the top-selling games in Japan were Pokemon games, but in the United States, three of the top four were Pokemon offerings. Also, “Super Smash Bros.” was fifth, and that game featured a couple Pokemon as well.

A handful of new food products debuted in 1999. Pepsi brought Sierra Mist into the world to try and strike a blow in the lemon-lime soda space. Meanwhile, Go-Gurt dared to ask, “What if yogurt came in a tube you could squeeze into your mouth like a crazy person?” Pepsi retired Sierra Mist in 2023 to replace it with Starry, and now the idea of squeezing yogurt into your mouth has been normalized. Time comes for us all.

It feels fitting to end this Y2K-inspired list with something from the technology space. The BlackBerry feels like it is from a bygone era, right? It feels quaint to those who don’t remember it and is nostalgically longed for by those who do. It had a qwerty pad! They even made a BlackBerry movie that was a straight-up period piece. Well, in 1999, the BlackBerry was brand new. Maybe that tells you just how much things have changed. That, or the whole Go-Gurt thing.