History of Hugh Hefner in Timeline

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Hugh Hefner

Hugh Marston Hefner was an American magazine publisher known for founding and editing Playboy magazine. Launched in 1953, Playboy gained notoriety for its inclusion of revealing photography and articles alongside content covering topics like literature, art, politics, and culture, sparking significant cultural impact and controversy.

April 9, 1926: Birth of Hugh Hefner

Hugh Marston Hefner was born on April 9, 1926, in Chicago.

1929: Birth of Keith Hefner

Hugh Hefner's younger brother, Keith Hefner, was born in 1929.

1944: Hugh Hefner Joins the Military

Hugh Hefner began serving as a writer for a military newspaper for the United States Army in 1944.

1946: Hugh Hefner Completes Military Service

Hugh Hefner finished his service as a writer for a military newspaper for the United States Army in 1946.

1949: Hugh Hefner Marries Mildred Williams

Hugh Hefner married Mildred Williams in 1949.

1949: Hugh Hefner Graduates from the University of Illinois

In 1949, Hugh Hefner graduated from the University of Illinois Urbana-Champaign with a Bachelor of Arts degree in psychology and double minors in creative writing and art.

1949: Marilyn Monroe's Photoshoot

Marilyn Monroe participated in a nude photoshoot in 1949, which was later featured in the first issue of Playboy in 1953.

January 1952: Hugh Hefner Leaves Esquire

In January 1952, Hugh Hefner left his copywriting job at Esquire after being denied a raise.

1952: Birth of Christie Hefner

Christie Hefner, the daughter of Hugh Hefner and Mildred Williams, was born in 1952.

December 1953: First Issue of Playboy Published

Hugh Hefner launched Playboy magazine in December 1953, with the first issue featuring Marilyn Monroe from a 1949 photoshoot.

1955: Playboy Publishes "The Crooked Man"

After Esquire magazine rejected Charles Beaumont's science fiction story "The Crooked Man" in 1955, Hugh Hefner published it in Playboy, sparking controversy for its themes of heterosexuality being persecuted in a predominantly homosexual society.

1955: Birth of David Hefner

David Hefner, the son of Hugh Hefner and Mildred Williams, was born in 1955.

1959: Premiere of "Playboy's Penthouse"

"Playboy's Penthouse," a television show hosted by Hugh Hefner, premiered in 1959.

1959: Hugh Hefner and Mildred Williams Divorce

Hugh Hefner and Mildred Williams divorced in 1959.

1960: End of "Playboy's Penthouse"

Hugh Hefner's television show, "Playboy's Penthouse," concluded in 1960.

1961: Hugh Hefner Discovers Dick Gregory

Hugh Hefner saw comedian Dick Gregory perform at the Herman Roberts Show Bar in Chicago in 1961 and hired him to work at the Chicago Playboy Club, giving Gregory's career a significant boost.

1962: Playboy Establishes "Playboy Interview"

Playboy introduced the "playboy interview" section in 1962, featuring in-depth interviews with influential figures.

June 4, 1963: Hugh Hefner Arrested on Obscenity Charges

On June 4, 1963, Hugh Hefner faced arrest for promoting obscene literature after Playboy published nude photos of Jayne Mansfield. The case resulted in a hung jury.

1963: Alex Haley Interviews Malcolm X

Alex Haley conducted an interview with Malcolm X in 1963 for Playboy's "playboy interview" series.

September 12, 1966: Hefner Debates The Playboy Philosophy on Firing Line

On September 12, 1966, Hugh Hefner participated in a televised debate on the program "Firing Line," where he engaged in a discussion with William F. Buckley Jr. about "The Playboy Philosophy."

1966: Alex Haley Interviews George Lincoln Rockwell

Commissioned by Hugh Hefner, Alex Haley interviewed George Lincoln Rockwell, the leader of the American Nazi Party, in 1966, for Playboy magazine.

1969: "Playboy After Dark" Premieres

Hugh Hefner began hosting "Playboy After Dark," a television show, in 1969.

1970: "Playboy After Dark" Concludes

"Playboy After Dark," the television show hosted by Hugh Hefner, came to an end in 1970.

1970: Hugh Hefner Criticizes "Militant Feminists"

Hugh Hefner openly criticized "militant feminists" in 1970, stating their opposition to the societal norms promoted by Playboy.

1971: Hugh Hefner Explores Bisexuality, Moves to Los Angeles

Hugh Hefner acknowledged experimenting with bisexuality in 1971. That same year, he established a second residence, Playboy Mansion West, in Los Angeles.

1975: Hugh Hefner Permanently Relocates to Los Angeles

Hugh Hefner permanently moved from Chicago to Los Angeles in 1975.

1976: Death of Hugh Hefner's Father

In 1976, Hugh Hefner's father, Glenn Lucius Hefner, passed away.

1978: Hefner Contributes to Hollywood Sign Restoration

In 1978, Hugh Hefner played a significant role in the fundraising efforts that led to the restoration of the iconic Hollywood Sign. He organized a gala fundraiser at the Playboy Mansion and made a substantial personal contribution to the project.

1979: Haley and Rockwell Interview Recreated in "Roots: The Next Generations"

The 1966 interview between Alex Haley and George Lincoln Rockwell was recreated in the 1979 miniseries "Roots: The Next Generations," with James Earl Jones portraying Haley and Marlon Brando as Rockwell.

March 7, 1985: Hefner Suffers a Stroke and Makes Lifestyle Changes

On March 7, 1985, at the age of 58, Hugh Hefner experienced a minor stroke, prompting him to reassess his lifestyle. He decided to reduce his involvement in extravagant parties and adopted a more subdued routine.

1988: Christie Hefner Takes Over Playboy's Commercial Operations

In 1988, Hugh Hefner's daughter, Christie Hefner, assumed control of Playboy's business operations, marking a significant shift in the company's leadership.

1990: Birth of Marston Glenn Hefner

Hugh Hefner's son, Marston Glenn Hefner, was born in 1990.

1991: Birth of Cooper Hefner

Hugh Hefner's son, Cooper Hefner, was born in 1991.

1992: Hugh Hefner Purchases Burial Spot Next to Marilyn Monroe

Hugh Hefner purchased the crypt next to Marilyn Monroe's at the Westwood Village Memorial Park Cemetery in 1992 for $75,000.

1992: Hefner Purchases Crypt Next to Marilyn Monroe

In 1992, Hugh Hefner purchased a crypt located directly beside Marilyn Monroe's final resting place at Westwood Memorial Park in Los Angeles.

1993: Hugh Hefner Voices Himself on "The Simpsons"

Hugh Hefner lent his voice to the character of himself in a 1993 episode of "The Simpsons" titled "Krusty Gets Kancelled."

1996: "Hugh Hefner: American Playboy" Airs

The biographical television special "Hugh Hefner: American Playboy," directed by Kevin Burns, premiered in 1996.

1997: Death of Hugh Hefner's Mother

Hugh Hefner's mother, Grace Caroline (Swanson) Hefner, passed away in 1997.

1998: Separation from Kimberley Conrad

Hugh Hefner and Kimberley Conrad separated in 1998 after a period of estrangement. Despite their separation, they continued to reside in close proximity, with Conrad moving into a house adjacent to the Playboy Mansion.

1999: Hugh Hefner Funds Clara Bow Documentary

Hugh Hefner provided financing for the documentary "Discovering the It Girl" in 1999, a film about actress Clara Bow.

2000: Hugh Hefner Appears on "Sex and the City"

Hugh Hefner made a guest appearance as himself in a 2000 episode of "Sex and the City."

2000: Hefner Shares Views on Religion

In a 2000 interview with Playboy magazine, Hugh Hefner openly shared his perspective on religion, expressing his belief that it was a myth created by humans to provide explanations for the unexplainable.

2005: Hugh Hefner Appears on HBO Shows

Hugh Hefner made guest appearances on the HBO shows "Curb Your Enthusiasm" and "Entourage" in 2005.

2005: "The Girls Next Door" Premieres

The reality television series "The Girls Next Door," which offered a glimpse into the lives of Hugh Hefner and his girlfriends, premiered in 2005.

2006: Details About Hugh Hefner's First Marriage Revealed

An episode of "E! True Hollywood Story" in 2006 revealed that Mildred Hefner permitted Hugh Hefner to have relationships with other women after she admitted to infidelity.

2006: Hugh Hefner Appears on "Robot Chicken"

Hugh Hefner made a guest appearance as himself on an episode of the animated television show "Robot Chicken" in 2006.

2006: Hugh Hefner Discusses Playboy's Origins

In 2006, Hugh Hefner revealed in an interview with E! that his mother provided $1,000 for the launch of Playboy, not because she believed in the venture but because she believed in him.

2007: USC School of Cinematic Arts Receives Donation and Renames Archive in Hefner's Honor

In 2007, Hugh Hefner made a generous donation to the University of Southern California's School of Cinematic Arts. In recognition of his contribution, the university decided to rename their audiovisual archive at the Norris Theater as the Hugh M. Hefner Moving Image Archive.

2007: Hugh Hefner Voices Himself on "Family Guy"

In 2007, Hugh Hefner provided his voice for a character on the animated sitcom "Family Guy."

October 2008: Departure from the Playboy Mansion

October 2008 marked a turning point as Holly Madison, Bridget Marquardt, and Kendra Wilkinson, who resided at the Playboy Mansion, collectively decided to depart from the residence.

January 2009: Relationship with Crystal Harris Begins

In January 2009, Hugh Hefner embarked on a romantic relationship with Crystal Harris, marking the beginning of their courtship.

2009: "The Girls Next Door" Concludes

After six seasons, the reality television series "The Girls Next Door" concluded in 2009.

2009: Daren Metropoulos Purchases Property Adjacent to Playboy Mansion

Daren Metropoulos, a principal at the private equity firm Metropoulos & Company, acquired a property located next to the Playboy Mansion in 2009.

2009: Hugh Hefner Receives Razzie Award Nomination

Hugh Hefner received a Golden Raspberry Award nomination for "Worst Supporting Actor" for his performance in the film "Miss March" in 2009.

2009: Hefner Files for Divorce from Kimberley Conrad

In 2009, Hugh Hefner initiated divorce proceedings against Kimberley Conrad after an 11-year separation. Hefner cited irreconcilable differences as the reason for the divorce.

2009: Hefner Expresses Desire to Spend Eternity Next to Marilyn Monroe

In a statement made to the Los Angeles Times in 2009, Hugh Hefner expressed his strong desire to have his final resting place next to Marilyn Monroe, considering it an irresistible opportunity to spend eternity by her side.

April 26, 2010: Hefner Makes Donation to Protect Hollywood Sign Vista and Endangered Rabbit Subspecies Named in his Honor

On April 26, 2010, Hugh Hefner made a substantial donation to a conservation group, providing the final $900,000 needed to purchase land and prevent development that would obstruct the view of the Hollywood Sign. As a tribute to his support for conservation efforts, an endangered subspecies of marsh rabbit was named Sylvilagus palustris hefneri in his honor.

July 30, 2010: Release of "Hugh Hefner: Playboy, Activist and Rebel"

"Hugh Hefner: Playboy, Activist and Rebel," a documentary about Hugh Hefner directed by Brigitte Berman, was released on July 30, 2010.

November 18, 2010: Hefner Receives Founder's Hero of the Heart Award

On November 18, 2010, Dr. Lois Lee, founder and president of the organization Children of the Night, presented Hugh Hefner with the first-ever Founder's Hero of the Heart Award. This special recognition was given to Hefner in appreciation for his longstanding dedication, commitment, and generous contributions to the organization's mission.

December 24, 2010: Engagement to Crystal Harris

On December 24, 2010, Hugh Hefner announced his engagement to Crystal Harris, signifying his commitment to their relationship.

2010: Finalization of Divorce from Kimberley Conrad

Hugh Hefner's divorce from Kimberley Conrad was finalized in 2010, concluding their marriage of over two decades.

June 14, 2011: Broken Engagement with Crystal Harris

Crystal Harris made the decision to break off her engagement with Hugh Hefner on June 14, 2011, just days before their scheduled wedding ceremony.

2011: Hugh Hefner Lends Voice to "Hop"

Hugh Hefner made a voice-only appearance as himself in the 2011 film "Hop."

2011: Hefner Declares Himself an Independent

In 2011, Hugh Hefner publicly identified as an independent, expressing his dissatisfaction with both the Democratic and Republican parties.

2012: Cooper Hefner to Succeed Father as Face of Playboy

Hugh Hefner announced in 2012 that his son, Cooper Hefner, would take over as the public face of Playboy.

2012: Hefner Supports Barack Obama's Reelection Campaign

In 2012, Hugh Hefner publicly endorsed and supported Barack Obama's campaign for reelection as President of the United States.

December 31, 2012: Marriage to Crystal Harris

On December 31, 2012, Hugh Hefner and Crystal Harris officially exchanged vows in a private wedding ceremony, solidifying their relationship as husband and wife.

January 2016: Playboy Mansion Listed for Sale

In January 2016, the Playboy Mansion was officially put up for sale with an asking price of $200 million. The sale came with the condition that Hugh Hefner would retain the right to live and work in the mansion.

April 8, 2016: Death of Keith Hefner

Hugh Hefner's brother, Keith Hefner, passed away on April 8, 2016, at the age of 87.

2016: Death of Keith Hefner

Keith Hefner, Hugh Hefner's brother, passed away in 2016.

April 2017: Release of "American Playboy: The Hugh Hefner Story"

The Amazon original series "American Playboy: The Hugh Hefner Story" was released in April 2017. The ten-episode series combined interviews, archival footage, and dramatic recreations to chronicle Hefner's life and career, from the founding of Playboy magazine to his personal relationships and impact on popular culture.

May 2017: Last Playmate of the Year Announcement at the Playboy Mansion

In May 2017, Hugh Hefner made his final Playmate of the Year announcement at the iconic Playboy Mansion, marking the end of an era.

September 27, 2017: Death of Hugh Hefner

Hugh Hefner passed away on September 27, 2017.

October 2017: Hugh Hefner biopic greenlit

In October 2017, a biopic about Hugh Hefner, directed by Brett Ratner and written by Jeff Nathanson, was greenlit by Playboy Enterprises, with Jared Leto rumored to be cast as Hefner.

November 2017: Biopic put on hold

Following sexual harassment allegations against director Brett Ratner in November 2017, the biopic about Hugh Hefner was put on hold indefinitely. Leto's representatives also denied his involvement with the film.

January 24, 2022: Secrets of Playboy Documentary Series Premieres

On January 24, 2022, a 12-part television documentary series titled "Secrets of Playboy" premiered on A&E. The series featured interviews with former employees and associates of Hugh Hefner, both male and female, who made allegations of a pattern of sexual misconduct and exploitation at the Playboy Mansion and other locations associated with Hefner.

January 2024: Crystal Hefner Releases Memoir Detailing Experiences at the Playboy Mansion

In January 2024, Crystal Hefner, Hugh Hefner's widow, published a memoir in which she shared her experiences while residing at the Playboy Mansion. In her book, she alleges that the environment was hostile and that she felt like a prisoner during her time there.

Mentioned in this timeline

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Marilyn Monroe
James Earl Jones
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Malcolm X
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