19 Things That Happened in 1999 That Will Make You Feel So Old

PayPal was deemed an awful business venture, for starters.

19 Things That Happened in 1999 That Will Make You Feel So Old

When it came down to it, 1999 was hardly the year Prince famously dreamed it would be. It was all about the butterfly clips, Britney Spears, and being scared of what the turn of the century would bring. From Pokémon still being a card game to the cost of a movie ticket, things have changed a whole lot in the 20 years since the ’90s ended. To remind you of the good times—and also to make you feel a little old—we’ve rounded up some of the most memorable moments of 1999.

Smart phones were only the apple of Bill Gates’ eye.

bill gates in the 90s, 1999 events Shutterstock

In 1999, business wiz Bill Gates released one of the most pivotal books to date, Business @ the Speed of Thought. In it, the Microsoft founder made many bold predictions about the future of technology. Among them? Social media, smart phones, online payment systems, and online job recruiting (hello, LinkedIn?). Hey, he’s not one of the richest men in the world for nothin’.

Everyone was in a full-blown panic about Y2K ruining computers.

Three year old girl plays with a TI 99 4a home computer, 1986. California, USA. Robert Clay/Alamy

Nowadays, our computer clocks change automatically as soon as Daylight Savings Time hits. But, back when the turn of the century was looming over everyone’s heads, people were certain the end of days was just around the corner. The Y2K scare came from projections that computers and computer networks would face catastrophic breakdowns once the clock struck midnight on Jan. 1, unable to recognize the year “2000” with the current software.

Even Time magazine was bracing itself for life after this alleged meltdown. “As police throughout the world secured emergency bunkers for themselves, the Time magazine and Time Inc. information-technology staff set up a generator-powered ‘war room’ in the basement of the Time & Life Building, filled with computers and equipment ready to produce the magazine in case of a catastrophic breakdown of electricity and communications,” then-assistant managing editor Howard Chua-Eoan wrote in the magazine’s commemorative 1/1/00 issue.

PayPal was voted one of the worst business ideas of the year.

paypal on a computer iStock

It’s rightfully considered one of the internet’s biggest successes today, but when PayPal first came out, it was actually voted one of the 10 worst business ideas of 1999. Luckily, things have come around for the online payment system since—and it’s now a billion-dollar brand used by nearly 300 million consumers.

Anybody could log in to any Hotmail account using the password “eh.”

old computer from the nineties, 1999 events Shutterstock

If you set your password as “password” in 2019 and someone hacks into your accounts, that’s on you. But back in 1999, that wasn’t exactly the case. The infamous “Hotmail hacking,” executed by a group known as “Hackers Unite,” brought to light a major security flaw with Microsoft. Widely regarded as one of the largest widespread security incidents in history, the hackers exposed an estimated 50 million Hotmail accounts, revealing that anybody could log in to any Hotmail account using the password “eh.”

Who Wants to Be a Millionaire? was the pinnacle of reality television.

Regis Philbin became famous after 40 Shutterstock

Who Wants to Be a Millionaire? first debuted in 1999, adapted from a popular British game show of the same name. First hosted by Regis Philbin, the series became a stepping stone for reality competition shows like Greed, Weakest Link, and Deal or No Deal. Of course, classic TV game shows like Jeopardy! and Wheel of Fortune came before it—but those weren’t nationwide appointment viewing like Millionaire. “The show’s glossy aesthetic and superhigh stakes attracted unprecedented audiences,” wrote Slate’s Justin Peters. “At its peak Millionaire was more popular than Monday Night Football.

Two decades later, the show was finally canceled, but its legacy lives on. After all: Who knows if we’d have Meghan Markle if it wasn’t for Millionaire?

The most sought-after laptops were billed as “to go” computers.


Before MacBooks were all the rage, Apple was gaining fame with its iBook line. The colorful, clamshell-styled laptops, released in 1999, were available in tangerine and blueberry, and nicknamed the “iMac to go.” Even at $1,600, these iMac offsprings were flying off the shelves.

DVD players were just starting to phase out VHS tapes.

vhs player things to throw away Shutterstock

These days, DVDs have lost traction as most people now watch their movies via online streaming services like Netflix. But back in 1999, DVDs were just starting to overtake VHS tapes as the technology du jour. The first DVD players arrived in 1997, but they racked up hefty price tags, costing more than $700. By 1999, however, the prices had dropped to around $200, and customers couldn’t wait to stop “being kind and rewinding” in favor of the DVD. And for more things facing a phase-out today, check out 25 Things That Could Become Obsolete Within the Next 5 Years.

Everyone was illegally downloading music without thinking twice.

Screenshot of Napster shows Madonna music downloads Northfoto / Shutterstock

These days, you can choose from services like Apple Music, Spotify, or Pandora to get music on all your devices 24/7 (and legally). However, back in 1999, Napster had just launched as the brainchild of Shawn Fanning and Sean Parker and was the only way to download music and file-share songs digitally. While it didn’t take long for labels and musicians to sue and shut down Napster in 2001, everyone who grew up in the 1990s and early 2000s remembers waiting patiently for that download to complete so you could make the ultimate Summer Jamz ’99 mix CD.

Britney Spears’ Rolling Stones cover was a huge scandal.

britney spears rolling stones 1999 cover Wenner Media

Before April 1999, Britney Spears was just another idolized teen pop star. But that year, she made her first move into provocateur territory with her 1999 Rolling Stone magazine cover and spread. The 17-year-old entertainer posed scantily clad in her underwear, holding the purple Teletubby (which had its own controversy, if you recall). “I think it’s sinful,” one man told Inside Edition of the photo. But for Spears, that was just the beginning of the decades of shock and scandal to come.

The first Teen Choice Awards took place.


For tween and teens today, it’s hard to remember a time before the Teen Choice Awards (if not impossible). However, the surfboard-centric event only got its start in 1999. And just who was attending the inaugural TCAs? Performers included Spears and *NSYNC, while most of the acting prizes ended up being handed to the stars of The WB.

Carson Daly pained his fingernails black and hosted TRL, not Today.

carson daly on TRL, 1999 events Alamy

Carson Daly is all over television screens these days, hosting shows like Today and The Voice. However, before he was the suit-wearing ringleader we know him as now, he was the less-refined host of MTV’s Total Request Live in 1999. Back then, Daly was most often seen sporting faded baggy jeans, black T-shirts, and his iconic black nail polish (on just two fingernails), as he introduced music videos featuring Backstreet Boys and Christina Aguilera.

“When I took the job, everybody said, ‘Stay in radio. What are you doing? It’ll be one year, and then you’ll be on a Noxzema commercial,’” he told the Los Angeles Times in 1999. “I never looked at it that way.” Clearly, he didn’t have to!

The national currencies of 11 European countries ceased to exist independently.

euro coin, 1999 Shutterstock

Whether you’re traveling to Spain, France, Ireland, or Italy today, you’re using the same exact currency—the euro. But before 1999, a standardized monetary system across Europe was just a utopian idea. After decades of preparations, the euro was finally introduced in 11 European countries on January 1, 1999. It’s hard to imagine that the second most widely used currency (following the dollar) wasn’t even around 21 years ago.

*NSYNC was the opening act for Janet Jackson.

n'sync with frosted tips in the 1990s Alamy

Today, Justin Timberlake is one of the biggest names in pop music. However, back in 1999, he was just one of the five members of *NSYNC, a boy band that was still trying to get its footing. Timberlake and co. released their first album in 1997 and didn’t catch on quite as quickly at the Backstreet Boys.

Instead, they rode on the coat tails of Janet Jackson, joining her Velvet Rope Tour from 1998 to 1999 as one of the rotating opening acts. “We don’t care if we get booed off the stage,” Chris Kirkpatrick told MTV at the time. “We’re just gonna be like, ‘What’s up Janet. You’re welcome. They’re ready for you.'” Booed? *NSYNC? Twenty-one years sounds like a lifetime ago!

A New York City councilperson protested $9.50 movie tickets.

movie theater Shutterstock

If you want to head to the movies these days, be prepared to shell out a pretty penny. The average movie ticket costs well over $9, and that doesn’t include possible up-charges for 3-D movies, midnight premieres, or extreme-surround sound. Back in 1999, however, you could usually score a ticket for a Lincoln and some change.

When Loews Cineplex (now AMC) raised ticket prices in Manhattan to $9.50 that year, a New York City council speaker issued a statement urging the Justice Department to intervene, deeming the increase “mugging of the middle class.” For comparison, an average Manhattan AMC ticket nowadays costs around $15.

Kids were robbing each other for Pokémon cards.

In 1999, the Pokémon franchise was exploding all across the United States. With the release of the Pokémon Red and Blue video game in 1998, “Pokémania” had taken over.

And while the game is still popular today, especially with the release of Pokémon GO, the craze in 1999 was unmatched—kids were even robbing each other to get their hands on certain Pokémon cards. “Hopefully, he had learned his lesson and won’t carry around as many cards anymore,” Tony Ward, a parent of a boy who was robbed of $60 worth of cards in Philadelphia, told the Associated Press in 1999. “I tell him when he goes out, he has to be more street-smart now.”

The first ever SpongeBob SquarePants episode aired.

spongebob squarepants first episode, 1999 IMDB/Nickelodeon Animation Studios

What else was taking over kids’ lives in 1999? SpongeBob SquarePants. Nowadays, SpongeBob has been so tightly woven into American society that it has evolved into two movies, a Broadway musical, and become a hotbed for internet memes. So it’s hard to believe the television show only first premiered in July of 1999 on Nickelodeon. Yes, 21 years ago, no one could’ve imagined a sponge who lived in a pineapple house and worked at an underwater burger joint.

The Real World was only in its eighth season.

mtv real world 1999 dvd cover Bunim/Murray Productions

June 2019 brought us the 33rd season of MTV’s The Real World. To put things in perspective, in 1999, the eighth season of the series was just kicking off. The reality show was set in Hawaii that season, and anyone who tuned in can remember Ruthie Alcaide’s departure from the show to enter rehab for her excessive drinking (after she jumped into the swimming pool naked, of course).

We learned how excellently Bruce Willis can play dead.

People weren’t exactly pressed for good movies in 1999—after all, The Matrix, Fight Club, and The Blair Witch Project were released that year. But when viewers found out that Bruce Willis had actually been dead the entire time in The Sixth Sense, it was the reveal to end all movie reveals.

We were only halfway through the Harry Potter book series.

third harry potter and the prisoner of azkaban book premiere, 1999 Alamy

With the success of J.K. Rowling’s first two books in the Harry Potter series, the third installment, Harry Potter and the Prisoner of Azkaban, was released to high expectations and high praise in 1999. Before any movie was even in sight, this book became highly regarded for pushing “Pottermania” into mainstream America. We had no idea what kind of magic was in store or who Daniel Radcliffe even was! And for more on the iconic series, check out the 35 Ways Harry Potter Is Still Crazy Relevant.

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