Despite its raciness and the controversy that occasionally surrounded it, countless celebrities posed for the groundbreaking adult magazine as a sort of Hollywood rite of passage.
Insiders said the shoot was designed to be reminiscent of the magazine's inaugural shoot with Marilyn Monroe.
Still, though, the announcement has some mourning the loss of an iconic cultural cornerstone.
Hugh Hefner later hinted on his Twitter that the Lohan issue was one of the best-selling in Playboy history.
It's probably one of the most memorable ones ever, though.