The first playtmate I ever saw was Venice Kong, and it was in the September 85 issue of Playboy that had the Madonna nude photos in it (which were terrible). Sorry for the size, couldn't find any other pics, the original photos are kinda obscure now
After that the next playmates I saw in a playboy which I took a strong liking too were Karin Taylor, Gillian Bonner, and Shauna Sand (pre-hideous plastic surgery and midlife crisis). IIRC, they were playmate of the month in 3 consecutive months in 1996, which makes sense because I remember my Dad getting those mags around that time each month.
Karin Taylor
Gillian Bonner
Shauna Sand
Shauna Sand went on to become a circus freakshow of plastic surgery as I'm sure we're all aware. I still have a soft spot for Gillian Bonner though because she was a web and graphic design nerd who started her own company and she also created her own (terrible) video game.