You know what, this made me realize a hilarious alternate reality/way things could have gone, where nothing got fixed in time, EVERYTHING printed dates like that, and after 2000 years we changed the dates again, with different aesthetic factions around whether to represent the date as "100" or "19100". (I would personally have been all over 5-digit years myself.)

Hmmmm. After thinking about that for a minute I realize that math and aesthetics do not mix and that one single format for years makes a lot of computers not get confused. I rest my case. :(

I’m sure I’ve seen websites in the last year or two from the 90s that still do this

Maybe it knows something we don't...

Is that the machine John Titor was after??

It looks like it matters. If it prints "100" then it's representing the year 2000 internally as the year 100 when the year 1995 is represented internally as 1995. If it prints "19100" then it's representing 2000 internally as 100 when 1995 is represented as 95. That second scenario doesn't cause any problems -- 2000 is still 5 years later than 1995, etc.

(Or, if the log is expected to print 95 instead of 1995, then 100 is what we expect it to print for 2000, but the difference still matters -- 19100 in that case would show that something was seriously wrong.)