What do you remember about the year 1999? What was that like for you and what do you remember most from that time?
I remember making lots of $$ off the Y2K stuff working as a freelance programmer. Oh and making absolutely ridiculous gains in the stock market (most of which were gone later). CMGI anyone?
I was working as a freelance graphic designer, but would go in every day to a small studio in downtown Birmingham, MI.
My kid was just 2 yrs old, so I was adjusting to that, and it was the year I not only saw The Matrix, but it was the first DVD I ever bought for my first DVD player that year.
Also, the New Years Eve party for Y2K at my sisters. Getting hammered and everybody still thinking something might happen when the clock turned over to 00:00 2000.
I was spending my first full year living abroad in Budapest, with my first out-of-college job as a photographer at a local English language business weekly there. I was not making silly amount of money ($700/month after taxes), but it was one of the best years of my life. I still miss it from time to time.
We were living in King George, VA and our daughter was in middle school. I remember the idiocy with Y2K - specifically a coworker who was bragging about his stores of beef jerky and ammo. He was READY!!!
He was an idiot. And not just about Y2K… 
Something’s wrong if you can’t remember 1999. I know exactly where I was and what I was doing. I also can give an approximate month timeline. 1997, 1994, 1991-2, 1990 were also all big years.
If you were born in 1998, you probably wouldn’t remember 1999. 
I wasn’t anywhere special. I will admit that I bought somewhat more non-perishable food than usual prior to The Big Day, but the intent of that was to cover emergencies to last a few days. I didn’t do anything at all re my savings - I assumed that the chances were so low that something would go weird with the banks that the nuisance of “preparing” financially far outweighed the risk.
As for the evening of 31/12/1999 I went to bed a little later than usual because I was watching 2000 being rung in around the world, but I didn’t even bother staying up until midnight my time (I am most emphatically an “early to bed and early to rise” person every day of the year)
About a foot to my left.
Working the same place I still work today and doing the same job.
While I had a different job and financial situation back then, for me the biggest difference would be that both of my parents were alive and relatively healthy then. Their illnesses and passing pretty much defined a great deal of the decade after that so that is what I think of most.
I was still living in Colorado, but had gone to Scotland for the holidays and had a flight from Heathrow to Barcelona scheduled for early Jan 1 2000. Before I left to drive down to London, I checked the interwebs (such as they were at the time) to see what mayhem had happened. Was amused that all the news sites were reporting “no news, Y2K not happening, business as usual.” Drove down to London and got stopped for doing 110mph on the M1 in my rented Ford Focus, then allowed to continue without getting a ticket. Thank you to English police officers that night!
The year 1999? Graduated college, and started my (very frustrating) job search. Mostly I remember desperately trying to get out of my hometown.
As far as 12/31/199, I started the milenium at a house party at my sister’s new house. Firecrackers went off all over the place at midnight. For whatever reason I think that was way better than spending the night out. Weren’t there a lot of really overpriced concerts and cover charges that year?
Sitting in the exact same spot I am now on most days.
I hadn’t retired yet, so I was still working, but it was nothing special.
I did teach my kids that although it was going to be 2000, the 21st century wouldn’t start for another year, but most didn’t want to hear it.
I made the last big trip with my dad before he became too sick to travel much. We went to Georgia and Armenia, with a few days in Moscow and Istanbul too.
Let’s see. I was working for a major pharmaceutical firm in their clinical trials department then. Both my daughters were in middle school. Married to the same woman and living in the same house I am now.
I remember a very amusing little sheep thing for the computer. Also the Straight Dope left AOL and started on this site.
Edited to add - I had a beard back then.
I think in the hospital having a double mastectomy… But it’s all a bit of a blurr
Partying.
Actually I was sitting in exactly the same spot as I am now, posting to this same message board.
Okay, my life officially sucks!
I remember walking.