Scan of a print photograph from, I want to say 1985? 1986? Something like that. My grandparents cat losing her damn mind because a fly got in the house.
Impromptu memorial on Las Vegas Blvd less than a week after the shooting in 2017. I was attending a conference that week, which they chose not to reschedule, because 'we can't let terrorism win!'
It was an eerie feeling being there so soon after.
Probably this scanned photo of my grandfather in WWII somewhere in France or Germany around 1943-44. He was a calculator for the 8th Armored Division 398th Armored Field Artillery Battalion M-7 tanks.
Me in 2015 in a box seat at Lincoln Financial Field. It was an Eagles preseason game and I had been doing an internship at a law firm that owned the box.
It was a fun few months but it convinced me not to go to law school. I still remember when one of the partners at the firm looked me dead in the eye and said “you know we have one of the highest suicide rates of any profession, right?”
Edit: second oldest photo is an article someone sent me over a year later, titled “Is communism cool? Ask a millennial.” Pretty sure it was written by some Heritage Foundation hack or something and I got into a spirited discussion with a family member over it.
An etch-a-sketch art piece from 2018. I used to make etch-a-sketch drawings when I was younger, mostly of trains and buildings. I think I liked the limitations of the method. I drew them while waiting in the room where my sibling took lessons, and while I later got my own, it doesn't work very well so I no longer do them.
(This isn't the same drawing, but it's close to the first, and doesn't contain my face in the reflection)
My phone started freaking out after a recent update and I was just about to go on a trip. So I hurriedly factory reset to get it functional and hoped all automatic backups were good. The critical ones were for sure, but stuff like camera roll I don't care about as much.
I haven't even tried to load and check the camera roll backup yet, meaning the oldest photo on my phone is a whopping two weeks old and is of my parking space number at the airport. It's a grey Camry, just about the most common color and the most common car. Man, I would never find it if I forgot where I parked it.
If we expand "devices" to my laptop and storage drives, the oldest photo is early 1900s. A shot of my great grandmother as a little girl standing outside the sod house she grew up in.
I've got the entire catalogue from the Royal photographic society 1870-1915 saved left over from my PhD. But the earliest of those are scans-of-sketches-of-photos because they pre-date the technology to easily duplicate photographs.
I took this to mean the oldest picture in my cloud account, because my phone manages its storage automatically.
According to the metadata, it’s from Apr 6, 2007. It’s from a trip to my grandma’s house. I don’t know why I took a picture of it. Anyone want to make them and send me one?
I won't post it but it's a picture of my old roommate with her almost crawling out of bed. Her bedroom is a disaster with old food plates, clothes everywhere, fast food bags, etc. Just a disaster. It wasn't gross, just very messy. She had just woken up and had been drinking the night prior.
I took a photo of it all from like 45 degrees up and stylized it in an oil painting style. I printed it out in canvas and gave it to her as a gift and titled it, "depression" she loved it and still has it.
Saved pic I used as reference for my Oath of Ancients Paladin idea from waaaaaaaay back that started out as basically Dinidan of the round table and The Green Knight and eventually turned into a tree.
Not easy to tell as I have a lot of old photo scans where I'm not sure of the original date. So let's try this terrible photo, which I think was the first on a roll taken sometime in the 1980s. I don't remember that bunny so I must have been very young.
I was disappointed to find out the oldest picture on my phone is a system icon file from 2017, two phones ago. I guess it tagged along on the external SD card.
Just a high score I got in a crummy mobile game I used to play where all you do is shout as a head and try to go as far as possible to the right. Circa 2018. Oldest saved photo I have on the phone I am currently using. Otherwise, it'd probably just be a picture from a school trip to Seattle.