1980
Hef champions for the reconstruction of the Hollywood sign and is honored with a star on the Hollywood Walk of Fame.
1981
Hef and 1982 Playmate of the Year Shannon Tweed become an item.
1981
Writer-director Cameron Crowe (Jerry Maguire) goes undercover for his September Playboy piece, "Fast Times at Ridgemont High," which will later be made into a movie.
1982
Christie Hefner is named president of Playboy Enterprises, Inc.
1983
Hef meets Carrie Leigh, a Toronto model shooting the magazine's April cover. By the time a pictorial of Carrie appears in July 1986, she and Hef are romantically linked.
1985
Hef suffers a stroke that changes the direction of his life. He refers to it as "a stroke of luck."
1985
Playboy wins the National Magazine Award for fiction.
1986
Hef commissions Andy Warhol to create the cover of the January issue.
1988
Hef's daughter Christie is elected chairman and CEO of Playboy Enterprises, Inc. Hef remains Editor-in-Chief of Playboy magazine and chairman emeritus of the corporation.
1989
Hef marries 1989 Playmate of the Year Kimberley Conrad in a ceremony seen around the world.