Probably this one:

(Also smart move to get some classic memes)

i’m so old i keep all my memes on my personal microcomputer, not my telephone.

Google photos has a date tag attached to this of 9/10/2008

A whole lot of stuff has traveled with me through the years swapping SD cards from one phone to another, and eventually things getting backed up to the cloud, etc. this is probably the oldest thing I have saved that can count as a meme. I don’t know if that date is when I actually first found it, when it first somehow got backed up, if maybe that’s just from some metadata left over from whoever made the meme originally, or something else entirely

But that date does generally feel about right, and the humor feels about right for high school-aged me.

From December 2021

This, apparently:

And this is the second oldest:

I didn’t realize so many people stored memes on their phones

Slumber Hulk (2004)

Metadata on this one shows June 2020 (I’ve had it since at least 2015 tho)

I downloaded this from Reddit on 6/22/12: