So, I was digging through some old boxes the other day. You know how it is, trying to clear out some space, and you stumble upon stuff you haven’t seen in years. Found a stack of old wrestling magazines from the 90s. Man, that took me back. It got me thinking about how we used to get our fix back then – waiting for the next issue, no internet spoilers, just grainy photos and articles written weeks after the event happened.

That trip down memory lane specifically made me think about The Undertaker. He was such a huge figure back then, totally unique. I got curious and decided, hey, let’s see what kind of old pictures of him I can find online now. It’s different from flipping through a magazine, that’s for sure.
My Search Process
First thing I did was just hop on the computer and start searching. Nothing fancy, just typed “Undertaker old pictures” into the search bar. Got a flood of images, naturally. A lot of it was newer stuff, or fan art, or pictures I’d seen a million times.
I realized I had to be more specific. I started trying things like:
- Undertaker early 90s photos
- Undertaker grey gloves
- Undertaker Ministry of Darkness era
- Undertaker vs Mankind pictures
That helped narrow it down a bit. Still had to sift through a lot, though. It’s funny, you find tons of pictures, but so many of them are really low quality. You can tell they were probably scanned from those same old magazines I was looking at, or maybe screen grabs from old VHS tapes. Finding really crisp, clear shots from his early days is tougher than you’d think.
What I Found
Managed to dig up some cool stuff eventually. Found some really old ones, back when he had the weirder greyish gloves and tie, looking super lanky. Then the classic purple era, which is what most people probably remember first.

Then there were the Ministry of Darkness pictures. Man, that whole period was something else. Lots of dark, moody shots. Completely different feel to his earlier stuff. It was quite a shift.
It was interesting seeing the evolution laid out like that. You forget how many different looks and phases he went through before the more recent “legend” status. I even stumbled on a few that looked like maybe they were behind-the-scenes, but it’s hard to tell for sure with old photos.
Compared to finding pictures of wrestlers today, where everything is high-definition and instantly available from a million angles, searching for these old Undertaker pics felt like a bit of an archaeological dig. It wasn’t super difficult, just took a bit of patience to filter out the noise and accept that not everything from back then was perfectly preserved in high resolution.
Anyway, it was a fun little project for an afternoon. Killed some time, brought back some memories. Much easier than actually scanning my old magazines, I guess, but definitely less satisfying than holding that physical copy.