I guess my oldest bought pinsim is Pinball Magic from 1989 on a 3,5 disc! Same goes for Crystal Caliburn (1993), Eight Ball Deluxe (1994) as well as Screamball (1993) on 5 discs running under DOS on a 80486 or compatible with 33Mhz or better!
Before this first steps with playable pinsims were made the existing ones were usually unplayable and with simple layouts, poor graphics and more or less unnatural physics why I call them trash. Well that were the first days of pinball simulation
The start of Windows 95 didn´t automatically ment that a pinsim would run under windows, until about 1998 still most pinsims ran on DOS. That means that you will have problems playing those games on PC´s with about 233 MHz and faster, meaning with almost every PC nowadays in use.
Emulators were made of the still large dosgame community. DOSBox simulates a PC of the necessary speed, so that several (not all) old DOS pinsims can be played again as in the past. Some other programms try to slow down the CPU but I don´t like this and I don´t know if dosgames will really work this way.
3D view didn´t exist in the beginning. Worse, many tables had a scrolling playfield (sometimes with the alternative to change to unscrolling smaller bird view). You had to aim without sight for targets etc. in the upper part and your eyes were strained to the limit. The alternative were playfields as high as the screen then usually only half the width. An angled view taking advantage of full screenwidth came already in 1996 but stayed a speciality of few programmers for still a long time.
Sierra started in 1996 with 3D views of playfields using the whole screen in width. A real appearence of a 3D view of a table was very well performed by Empire when starting the Pro Pinball series with their first pinsim.
Timeshock released 1997 with excellent graphics, physics and a table layout you could expect from a real pinball machine.
Pure Pinball might outperform it with a still more brilliant graphic but Timeshock stays in my opinion the best pinsim there is.
Again it seems Sierra who first used animated targets, in 1997 Wildfire followed with Balls of Steel. Oddly enough, animated (moving) targets remained a rarity. Actually that should have been an important chance and advantage of PC pinball simulation against real machines for layout and gamefun.
Astonishing that implemented videogames started even before 1996. More frequently in 1997+98 in Timeshock, Judge Dredd and Pinball Addiction. Some of the videogames are really tricky and need some practice to master.
It seems strange to me that software developers still produces scrolling pinsims after Pro Pinball releases and even nowadays. Realistic ball physics seems to be for some of them still unprogrammable. They are getting closer but still don`t quite catch up to the Pro Pinball series, Pure Pinball or Thrillride of Sierra or the freeware Visual and Future Pinball! So you still won´t be sure what you will get when buying a new pinsim CD.