Tomb Raider II.

I had a Saturn, and I played the first one on it. Then I got a PSOne, and then got TRII for it. I didn't get deep into PlayStation's world until the PS2. I bought one in 2002 together with Final Fantasy X and MGS2. I don't remember which one I booted first, but I consider that my real beginning with PlayStation.

The first thing I played was the Tekken 2 demo.  I thought it was awesome.

First game I bought was probably Final Fantasy VII.  That game was the reason I turned traitor to Nintendo, after all.  

Ridge Racer, Battle Arena Toshinden, Warhark, and Destruction Derby. Can't remember which I popped in first for suuuure. Think it was Ridge Racer. I tried the CD trick fairly quickly with a few different CD's.

Crash Bandicoot 2: Cortex Strikes Back.

Jumping flash. Damn that was an awesome game.

i got two games with my PS1

The first one i ever played:

This was the other game i got

Pretty sure it was either between Rascal or Crash Bandicoot. Followed by Guardian's Crusade.

Final Fantasy 7. I bought a Playstation so that I could play Fantasy 7. It was worth every penny.

Vigilante 8. Played all the time with friends. I miss this game.

The first game I ever played on a Playstation system was either Crash Bandicoot 3 or Medievil from what I can remember.