Hugh Hefner Through the Years: A Timeline of the Playboy Founder's Life

Remembering Hugh Hefner

Hugh Hefner, the Playboy magnate and lifelong champion of liberal philosophy, free expression, and sex-positive sophistication, died at 91 at the Playboy Mansion in Los Angeles on Sept. 27. Born Hugh Marston Hefner on April 9 in Chicago, the mogul was the oldest of Glenn and Grace Hefner’s two sons. Here, we look back at just a few of his most memorable achievements over his storied life.

1940

As a student at Steinmetz High School, Hefner founds the school newspaper, presides over the student council, and demonstrates the beginnings of a wicked sense of humor with a quasi-autobiographical comic book, School Daze.

1944-1949

Hefner begins serving in the U.S. Army in a noncombatant role as an infantry clerk and a writer/cartoonist for military newspapers. He’s discharged in 1946 at the end of the war.

Hefner marries Mildred Williams and graduates on an accelerated track from the University of Illinois at Urbana Champaign, with a B.A. in psychology and a double minor in creative writing and art. He also cartoons for the paper and edits the campus humor magazine Shaft, introducing its “co-ed of the month” feature.

1951

Hefner moves away from his cartooning dreams and takes serious steps into the magazine world as a copywriter of promotional material at Esquire.

1953

Deciding not to follow Esquire when the magazine moves its operations to New York, Hefner (after a false start) launches his own publication in December: Playboy, which he names after rethinking possible trademark complications from his first title idea, Stag Party.

1953

To found the magazine, Hefner puts up his furniture and raises $8,000 from investors. The first issue sells over 50,000 copies (almost doubling how much he needed to sell to break even) and features a photograph Hefner purchased of a nude Marilyn Monroe from a 1949 shoot.

1954

Hefner begins to make waves with his new magazine which, as of its second issue, features its now-iconic rabbit logo. While pushing an aspirational, sex-forward adult aesthetic and lifestyle as well as a philosophy of bachelorhood-cum-sophistication, Hefner also makes a splash publishing challenging and cerebral stories by authors like Jack Kerouac, Kurt Vonnegut, Haruki Murakami, Ray Bradbury, Roald Dahl, Norman Mailer, Ian Fleming, Gore Vidal, and Margaret Atwood. Playboy also memorably publishes Charles Beaumont’s groundbreaking story “The Crooked Man,” which marks Hefner as an early advocate for gay rights.

1959

After having two children, Christie and David, Hefner divorces Mildred Williams (not pictured) and dips a toe into television with the short-lived syndicated 1959-60 series Playboy’s Penthouse. Featuring guests like Ella Fitzgerald, Cy Coleman, Bob Newhart, Nina Simone, Lenny Bruce, and Tony Bennett, the show transcends its bachelor-pad talk-show style by notably eschewing racial barriers and desegregating its performers (an inclusive belief Hefner would also push with the integration of his Playboy Clubs in 1961).

The ‘60s

By 1960, Playboy would have more than a million subscribers. As Hefner’s smoking-jacket bachelor aesthetic becomes his (and the brand’s) signature look, Playboy itself enters a golden age, debuting its now-iconic “Playboy Interview” (beginning with an interview with Miles Davis by author Alex Haley) and developing an enterprise of private pleasure clubs across the country (the first being in Chicago in 1960) that would introduce the “Playboy Bunny” hostess and peddle Hefner’s brand of “new hedonism” philosophy. He’d also write a series of editorials detailing exactly that philosophy in the magazine, which he counterbalanced with challenging pieces and interviews.

1963

Hefner stands trial for obscenity sale charges after an issue of Playboy featuring naked photos of actress Jayne Mansfield generates controversy. The charges are dropped thanks to a hung jury, and a year later, Hefner would found the Playboy Foundation as just one in his long string of personal efforts to combat censorship.

1969

Hefner hosts his second weekly talk show, Playboy After Dark, featuring guests like Sammy Davis Jr., James Brown, Ike and Tina Turner, Linda Ronstadt, and Milton Berle.

1971

Hefner buys the Los Angeles home that will become the modern Playboy Mansion.

1971

Playboy Enterprises goes public and the brand becomes a publishing, modeling, merchandising media empire. According to Playboy, the magazine is capping out at seven million issues sold a month and over 900,000 members worldwide at the company’s resorts, hotels, casinos, and Playboy Clubs (totaling 23). Competition from rival magazines like Hustler and Penthouse also contributes to what would be the beginning of a decline for the magazine.

1975

Hefner moves into the Playboy Mansion in Holmby Hills, Calif., full-time.

1978

Hefner raises funds for the restoration of the Hollywood Sign (personally purchasing the letter Y).

1979

He starts the official Playboy Jazz Festival (technically, it’s the second one, after a one-time stint in Chicago). Hefner’s daughter Christie creates the Hugh Hefner First Amendment Award to honor individuals like her father who significantly contributed to the evolution and protection of free speech.

1980

Hefner gets a star on the Hollywood Walk of Fame.

1982

Hefner makes a guest appearance during season 8 of Laverne & Shirley, in which he plays himself and Carrie Fisher plays a Playboy Bunny.

1985

Hefner suffers a stroke — which he calls “a stroke of luck.” As legend goes, he joked that a book about the murder of a former Playmate caused him the stress.

1988

Hefner names his daughter Christie chair and CEO of Playboy Enterprises, effectively relinquishing control of his company’s new media expansion while still remaining editor-in-chief of the magazine (and choosing its Playmate of the Month).

1989

Hefner marries his second wife Kimberly Conrad, with whom he would have two sons, Marston and Cooper (the CEO of Playboy Enterprises as of 2017).

1989

Hefner and Conrad separated a decade after getting married, and divorced a decade after that. During his storied bachelorhood, Hefner always had a reputation for bedding women. “How could I possibly know [how many]? Over a thousand, I’m sure,” he told Esquire. “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.”

1995

Throughout the decade, his life as a publisher and philanthropist earns him dozens of prestigious awards (from groups like the Magazine Publishers of America and the New York Friars Club) and he cultivates a meaningful long-term relationship with the film school at USC, where he would later donate $2 million dollars to help fund and exhibit student films. He also continues his fight against censorship and in 1998 he’s inducted into the Hall of Fame of the American Society of Magazine Editors.

2005

Hefner re-enters the spotlight with six seasons of The Girls Next Door, a hit reality series on E! revolving around Hef and his girlfriends: Holly Madison, Kendra Wilkinson, Bridget Marquardt, Kristina Shannon, Karissa Shannon, and Crystal Harris (his eventual third wife).

2010

Hefner sets the Guinness World Record for longest-running editor of a magazine. He also sets one for the largest personal scrapbook collection (documenting, essentially, his whole life). That year, he proposes to Harris.

2012

Hefner marries Crystal, who was 26 at the time.

2016

The Playboy Mansion in Los Angeles is sold, with a stipulation that allows Hefner to live there for the rest of his life.

2017

Hefner dies at 91 at his home, the Playboy Mansion. He will be buried in the Los Angeles crypt he purchased in 1992… the one located directly next to Marilyn Monroe’s.