| Year |
Age |
Event |
| 1926 |
0 |
Born in Chicago, Illinois |
| 1934-1944 |
8 |
Attended Steinmetz High School |
| 1944-1946 |
18 |
Served in the US Army |
| 1946-1949 |
20 |
Attended University of Illinois, graduated with B.A. |
| 1949 |
23 |
Married Mildred Williams |
| 1952 |
26 |
Daughter Christie born |
| 1953 |
27 |
Launched first issue of Playboy |
| 1954 |
28 |
Son David born |
| 1955 |
29 |
Published “The Crooked Man” in support of gay rights |
| 1956 |
30 |
Cleared of charges of distributing lewd material |
| 1959 |
33 |
Divorced from Mildred Williams |
| 1960 |
34 |
Moved to Chicago’s Gold Coast |
| 1963 |
37 |
Opened first Playboy Club in Chicago |
| 1964 |
38 |
Founded the Hefner Foundation |
| 1965 |
39 |
Launched “Playboy’s Penthouse” TV show |
| 1967 |
41 |
Moved to Los Angeles, bought the Playboy Mansion |
| 1971 |
45 |
Launched first international edition of Playboy in the UK |
| 1976 |
50 |
Received First Amendment Award from ACLU |
| 1978 |
52 |
Helped restore the Hollywood Sign |
| 1988 |
62 |
Daughter Christie became CEO of Playboy Enterprises |
| 1989 |
63 |
Married Kimberley Conard |
| 1990 |
64 |
Son Marston born |
| 1991 |
65 |
Son Cooper born |
| 2000 |
74 |
Launched playboy.com |
| 2003 |
77 |
Celebrated 50th anniversary of Playboy |
| 2005 |
79 |
“The Girls Next Door” TV show premiered |
| 2006 |
80 |
Inducted into the Television Hall of Fame |
| 2009 |
83 |
Appeared in “Miss March” |
| 2010 |
84 |
Divorced from Kimberley Conard |
| 2011 |
85 |
Received Legacy Award from National Lesbian and Gay Journalists Association; supported Obama’s reelection |
| 2012 |
86 |
Married Crystal Harris |
| 2017 |
91 |
Died on September 27 |
