iTools > .Mac > MobileMe > iCloud. Still on the original address. January 2000.
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My main email account, which is from the year 2000.
Yahoomail account. Created it in the early 2000s, stopped using it around 2009 when I moved on to newer email providers. I remembered I still had it last year when I got an emai on my recovery email that they will be deleting my account if I don’t login. I somehow was still able to recover it and login after 15 years. Now I just login whenever I get a notification of inactivity. I don’t actually use it for anything anymore.
My proboards account, made in 2004.
YouTube! I've been using the same account since 2008. They actually had to makeup an email for it since my account was before the Google merge.
i believe my neopets account is older than my youtube account, so that. actually went to playing neopets again fairly recently to see how its changed
My Twitter account is from 2014 and I still use the same one. My youtube account is even older but no idea how old. On places like Reddit and Lemmy I make a new account atleast once a year.
Still active. Probably Steam.
Bank account is first, use it everyday. Second would be apple id.
I think a spare email I use for peripheral stuff is from mid-late 1990s. Maybe 1996.
My Yahoo Mail was opened the first week of January, 1998. Would be my Hotmail account, but I made my Yahoo account because Microsoft bought Hotmail, and stopped using Hotmail
A 2002 eBay account
My memory is terrible, and it doesn't help that I have the world record for the most sites having signed up for (a very nerdy bragging right I have), but it has to be something like one of the Pokemon MMO's, RuneScape, or Furaffinity (RIP Dragoneer). Most of the old places I've been to are gone one way or another, for example I haven't heard from Postopia since the E3 disaster.