First match I remember seeing was Hogan vs. Warrior at WrestleMania 6. I recall seeing some WCW around the same time and was an instant fan of Sting - I even had a few of the WCW action figures, which IIRC, included Sting and Brian Pillman.
I recall seeing some ECW, don't know the year, but I was young enough for my mother to censor my viewing it after she saw bloody faces.
My memory becomes clearer during the Attitude Era, particularly of Stone Cold. I was grounded from watching wrestling after me and a few friends at school had a Royal Rumble match and I gave one of them a Stone Cold stunner...and subsequently got suspended for it. I followed Goldberg all throughout 1998, and this is when I became aware of Chris Benoit if memory serves right. During this time I had the N64 and the IMO, very best wrestling games ever made: WCW/nWo Revenge, WWF No Mercy, WWF WrestleMania 2000 and WCW vs. nWo: World Tour.
I became involved in the tape trading scene in 2000 or 2001, which is when I was exposed to puro, joshi and lucha. I took an instant liking to puro, especially All Japan and the New Japan juniors. I continued watching wrestling after graduating high school and joining the Marines. When I was in the fleet I ordered some DVDs from Will, the 2005 MOTYC set IIRC.
After getting out of the Marines, I continued watching regularly until June 2007, when the Benoit murders happened. After that, I sporadically watched, mainly All Japan from the '90s. My interest waned considerably thereafter following a family tragedy. I downloaded a few matches here and there that had received praise, but otherwise didn't watch much of anything wrestling related on any sort of regular basis.
It wasn't until recently that I started watching wrestling again, mostly documentaries or compilations I could find on Youtube.