1968-1970 - Co-host of television program, "Playboy After Dark."
1971 - Buys the Playboy Mansion West in Holmby Hills, California.
1971 - Monthly circulation of Playboy peaks at seven million issues, the same year the company goes public.
1972 - The first overseas addition of Playboy magazine is launched in Germany.
1975 - His daughter, Christie, joins the company as special assistant to the chairman.
1980 - Receives a star on the Hollywood Walk of Fame for his efforts championing the reconstruction of the Hollywood sign.
1982 - Christie Hefner is named president of Playboy Enterprises, Inc.
March 1985 - Suffers a mild stroke.
1988 - Hefner steps down as chairman and CEO and his daughter, Christie, takes control. He remains active in various editorial duties, including choosing the Playmate of the Month. (Christie Hefner serves as CEO until 2009.)
1989 - Playboy Enterprises moves to smaller offices on Chicago's Lake Shore Drive.
1992 - Purchases the crypt next to Marilyn Monroe's in the Westwood Village Memorial Park cemetery for $75,000.
- Donates $100,000 to the University of Southern California to fund a course, Censorship in Cinema.
1995 - Donates $1.5 million to the University of Southern California to endow the Hugh M. Hefner Chair for the Study of American Film.
April 1998 - Is inducted into the American Society of Magazine Editors Hall of Fame.
1998 - Wife Kimberley and their two sons move into a house adjacent to the mansion after the couple separate.
August 7, 2005 - August 8, 2010 - "The Girls Next Door" airs. The cable reality series stars Hefner and his three girlfriends Holly, Bridget and Kendra.
November 2007 - The University of Southern California's School of Cinematic Arts receives a $2 million donation from Hefner.
March 5, 2009 - April 10, 2009 - Guest curator at the UCLA Film & Television Archive's Humphrey Bogart retrospective.
December 24, 2010 - Proposes to Crystal Harris, 24, Playboy's December 2009 Playmate of the Month.
June 14, 2011 - Hefner reports on Twitter "The wedding is off. Crystal has had a change of heart." The ceremony was scheduled for Saturday, June 18 at the mansion.
October 4, 2011 - NBC cancels "The Playboy Club," a television drama based on the original Playboy Club set in the early 1960s, after three episodes.
January 2012 - Playboy Enterprises Inc. announces that its headquarters will move from Chicago to Los Angeles by the end of April.
December 1, 2012 - Announces his engagement to Crystal Harris is back on.
March 2013 - In an interview for Esquire magazine, Hefner claims the number of women he's slept with is "over a thousand, I'm sure. There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn't married. You have to keep your hand in."