December 31, 1999 was a Friday. I know this because I was young, living with my parents, and working as a pizza delivery guy. Sunday through Thursday nights, the store closed at 11PM, but on Fridays and Saturdays, the store closed at 1AM, meaning one unlucky driver would be scheduled to work New Years Eve. That unlucky driver was me.
My boss, a franchise owner with a single store and every penny of his life's savings invested in his business, was working, but he needed a driver. Everyone else clocked out one by one as the dinner rush ended and ran home to shower and get ready to party. My boss consoled me with the fact that I'd be making "tons" of money, since I'd be the only delivery driver and everyone would be drinking and therefore ordering lots of pizza.
None of this was true. We were less busy than a normal Friday night. I think I made 70 whole dollars in tips in a 10 hour shift. At 11:59 PM on December 31, 1999, I was staring at a Domino's Pizza monochrome CRT display, waiting to see if it would freak out and crash then the clock flipped to midnight. It didn't. I rang in the year 2000 with my immigrant boss, who hated his wife, resented Americans for their lack of a work ethic, and ended up getting out of foodservice entirely just a few years later.