October is a special month in the history of Playboy magazine. Not only was it the month of our college-themed issue for years, but this particular month has featured numerous star-studded covers, featuring everyone from Barbara Streisand and Burt Reynolds to Jerry Seinfeld and Cindy Crawford. Aside from celebrities, iconic Playmates have also graced the October cover, including Cathy St. George, Pamela Anderson and Sara Jean Underwood. The most notable October cover may be the one with Darine Stern, the first African-American woman to appear on Playboy by herself.
Scroll through to view the evolution of Playboy’s October cover throughout the years.