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AskMen Turns 20: All About the Year 1999
1999 was a year that will go down in history as the last good year of the twentieth century. That’s a quite literal statement seeing as it was the last year of the century, but we digress. Once the clock struck midnight on January 1, 2000, the world did not in fact end, we could still party hard — regardless of what the Prince had to say about it — and we got to start retraining our brain to write 20 instead of 19 when writing out the dates on our checks. Oh yeah, we still used checks.
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The year 1999 had a lot of great things going for it, before all the never ending social media, taking shoes off to get through airport security and self-driving car crashes, 1999 brought us one of the most important things in the history of the entire world — AskMen. OK, maybe not one of the most important things, but pretty damn great. But not the AskMen you see before you today. This was an AskMen started in a coffee shop in Montreal, Canada by Ricardo Poupada and Christopher Rovny with one mission in mind that still rings true today, 20 years later — being a better man.
So what was going on in 1999 all around founders Poupada and Rovny to consciously or subconsciously influence their AskMen decision making? We took a deep dive into the last year of the twentieth century to see what we wore, what we watched and how we worked.
What We Wore in 1999
In 1999, we were seeing the decline of grunge and JNCOs (or so we thought) and the rise of Americana pop stars like Britney Spears and the Backstreet Boys. These young faces were setting new rules that would go on into the 2000s. Inspiration was also coming from movies such as “The Matrix” and “10 Things I Hate About You” which were stylishly stripped down versions of their predecessors like “Total Recall” and “Empire Records,” also ‘90s movies, but in a totally different sense.
American Designers Were in High Demand

Ralph Lauren, Calvin Klein, Tommy Hilfiger
Trips to the Mall Were Common

GAP, Abercrombie and Fitch, Journeys
Outfits Were Comfortable, Not Complicated

3-4 Button Blazer, Tommy Hilfiger Jeans, Black Leather Coat
What We Watched in 1999
Well, whatever we watched, chances are we watched it either in the theatres or on a VHS rented from Blockbuster. TiVo was out, but just barely — it was launched in January 1999. So unless you were literally the coolest kid in school, you were probably checking out the social scene at Blockbuster on a Friday night like the rest of us. If you were one of those guys who wanted to get out of the house and go the multiplex at the mall, then believe it or not, you were only dropping $5 on average for the price of admission — it’s almost double that today.
Best TV Shows of 1999

Who Wants to Be a Millionaire, ER, Friends
Top Grossing Films of 1999

Star Wars: Episode I - The Phantom Menace, The Sixth Sense, Toy Story 2
Oscar-Winning Movies in 1999

American Beauty, Boys Don’t Cry, The Matrix
Top News Stories of 1999

President Clinton was acquitted, JFK Jr.’s plane crashed, Jeff Bazos won “Time” magazine’s Man of the Year Award
Top Sports Stories of 1999

Denver Broncos won the Super Bowl, New York Yankees won the World Series, Women's Soccer Team won the World Cup
What We Were Listening to in 1999
If you were an audiophile in 1999, chances are you were rocking out to the sweet tunes coming from your Sony Walkman, since there wasn’t an Apple product to provide music out of thin air. The latin invasion of 1999 was launched by heartthrob Ricky Martin, formerly of boy group Menudo, who would later come out as gay in 2010. Other latin superstars such as Enrique Iglesias, Marc Anthony and Jennifer Lopez (pre J. Lo) soon followed suit.
Just because Martin broke out of his boy band doesn’t mean the boy band-formula wasn’t still going strong. We have that formula to thank for bands such as LFO, Hanson, 98 Degrees, Boyz II Men, *NSYNC and The Backstreet Boys. In fact, The Backstreet Boys broke the record for highest sales in the first week of release with their fourth album Millennium. It sold over 1.5 million copies in the first week, which was a record previously held by Garth Brooks.
A Few Top Songs of 1999

“Believe” by Cher, “...Baby One More Time” by Britney Spears, “Every Morning” by Sugar Ray
A Few Grammy Song Winners of 1999

Smooth by Santana feat. Rob Thomas, No Scrubs by TLC, Scar Tissue by Red Hot Chili Peppers
A Few Grammy Album Winners of 1999

Supernatural by Santana, Fanmail by TLC, Fly by Dixie Chicks
What We Ate in 1999
1999 didn’t bring any groundbreaking culinary cuisines our way — with the game-changing exception of the Subway fast-food diet invented by now-convicted child sex offender Jared Fogle. However, foods we think of as the total norm today, such as sun-ripened tomatoes and calamari, were fresh on consumers minds in ‘99.
Where We Were Getting Our Food in 1999

Kroger, Subway, Starbucks
The Foods We Loved in 1999

Red Bell Peppers, Crab Cakes, Cosmos
How We Worked in 1999
In 1999, under then President Clinton, the U.S. economy entered its 9th year of expansion, unemployment was at a 30-year low at 4.1 percent (only slightly higher than the 3.7 we see today). More than half of all job growth in 1999 was in services, and companies that provide services to businesses led the way — perhaps a sign of the service-based economy that was to come with Uber, Seamless and of course, Amazon (which was founded in 1999 — coincidence?).
Wall Street stocks closed out 1999 — literally on Friday, December 31 — at an all-time peak after a century of unprecedented growth punctuated by two market crashes, the longest-running stock rally in history and the emergence of technology companies as future leaders to come.
Technology Developments that Changed Our Lives in 1999

BlackBerry, USB Drives, Apple iBook
Internet Launches That Changed Our Lives in 1999

Internet Explorer 5, Napster, MySpace
With all that has gone on since AskMen launched as a humble site for the modern man in 1999, we have to wonder, what will the modern man be thinking about 2019 in 20 years time? We hope the footprint we have left so far has helped men become better versions of themselves, and we hope the steps we take in the future will only keep the trend going.
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