10 major moments from Hugh Hefner’s career

Playboy Magazine founder Hugh Hefner built an empire publishing nude photos and high-quality interviews. Over the years, he also became known for as a reality TV Star and philanthropist as well as a media mogul. Here are 10 key moments from Hefner’s groundbreaking career.

Leaving Esquire

In 1952, Hefner worked as a copywriter at Esquire. After being denied a $5 raise, he quit the magazine, determined to start his own. He took out a mortgage of $600 and raised another $8,000 from 45 investors, including $1,000 from his own mother.

Playboy’s first issue

Hefner used the seed money to start Playboy Magazine (although the name changed: It was originally going to be called Stag Party, but Hefner couldn’t use that name because someone else owned the trademark). The first issue hit newsstands in 1953, featuring nude photos of Marilyn Monroe from a 1949 calendar shoot. The issue was a hit, selling 50,000 copies.

66 PHOTOS
Hugh Hefner through the years
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Hugh Hefner through the years
LOS ANGELES - JUNE 26,1957: Hugh Hefner with Joan Bradshaw at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26: Playboy Magazine founder and publisher Hugh Hefner attends a party in his honor with actresses Joan Bradshaw (right) and Susanne Sidney on June 26, 1957 in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26,1957: Hugh Hefner and guest at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26,1957: Hugh Hefner with Joan Bradshaw and girls at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
American pornographer Hugh Hefner and murdered Playboy PLaymate Dorothy Stratten (1960 - 1980), 1980. She holds a plaque naming her 1980 Playmate of the Year. (Photo By Julian Wasser/Online USA Inc./Getty Images)
American publisher Hugh Hefner smokes a pipe and holds a pamphlet while balancing a briefcase on his knee, c. 1960. (Photo by Authenticated News/Getty Images)
Show Business Illustrated magazine
(Original Caption) 1/29/1962 -New York,NY -: Hugh M. Hefner, Editor and Publisher of Playboy, is shown with Cynthia Maddox, the blond cover girl on the February issue of his magazine, arriving by TWA superjet from Chicago. They are here to attend a party given by Ella Fitzgerald at the Basin Street East in honor of winners of the Playboys jazz poll.
(Original Caption) Hugh Hefner, publisher of Playboy Magazine, shown as he appeared in court to face charges that nude photograph of Jayne Mansfield in the June issue are obscene. Hefner's attorneys asked for a continuance and his trial was set for July 9 in Municipal Court.
26th June 1966: American millionaire Hugh Hefner, founder of the Playboy empire, during a visit to Britain. (Photo by John Downing/Express/Getty Images)
Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport. (Photo by Dove/Getty Images)
Heff, is in Britain to officially open his 16th Playboy Club, located in Park Lane, London. (Photo by Sunday People/Mirrorpix/Mirrorpix via Getty Images)
Hugh Hefner Boss of the Playboy Empire arrives with an entourage of Bunny Girls at London Heathrow Airport, Saturday 25th June 1966. Heff, is in Britain to officially open his 16th Playboy Club, located in Park Lane, London. (Photo by Sunday People/Mirrorpix/Mirrorpix via Getty Images)
Playboy CEO Hugh Hefner with partner model, actress and singer Barbara Benton arrive at Paris Airport. (Photo by James Andanson/Sygma via Getty Images)
(GERMANY OUT) Hefner, Hugh *09.04.1926-Verleger (Playboy), USA - mit seiner Freundin Barbara Benton waehrend eines Besuchs in Berlin- 1969 (Photo by Binder/ullstein bild via Getty Images)
Portrait taken on August 21, 1970 at Le Bourget airport shows US Playboy Magazine publisher Hugh Hefner and his girlfriend actress Barbara Benton. AFP PHOTO (Photo credit should read STRINGER/AFP/Getty Images)
UNSPECIFIED - CIRCA 1970: Photo of Hugh Hefner (Photo by Michael Ochs Archives/Getty Images)
UNSPECIFIED - CIRCA 1970: Photo of Hugh Hefner Photo by Michael Ochs Archives/Getty Images
Publisher Hugh Hefner and Actress Julie Newmar attend the Rugby Ball on October 20, 1972 in New York City, New York. (Photo by Ron Galella/WireImage)
HUGH HEFNER -- Pictured: (l-r) Hefner's girlfriend/Singer, Barbi Benton, unknown, Playboy founder Hugh Hefner discussing promotional artwork for Barbi's 1974 debut album 'Barbi Doll'-- Photo by: Ron Tom/NBCU Photo Bank
American publisher Hugh Hefner, of Playboy Enterprises, smiles with his girlfriend, American actor and model Barbi Benton as they attend the 21st annual SHARE fund raiser for The Exceptional Children's Foundation. She wears a feathered blouse and he holds a pipe. (Photo by Frank Edwards/Getty Images)
Hugh Hefner and bunnies during 5th Annual International B Bunny of the Year Pageant at The Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by Ron Galella/WireImage)
Hugh Hefner and Sondra Theodore attend Hugh Hefner's Special 25th Anniversary Party on January 10, 1978 at New York New York Disco in New York City. (Photo by Ron Galella/WireImage)
Hugh Hefner and Sondra Theodore attend 25th Anniversary Party for Playboy Magazine on January 11, 1979 at Tavern on the Green in New York City. (Photo by Ron Galella/WireImage)
NEW YORK, NY - CIRCA 1979: Hugh Hefner and Sondra Theodore circa 1979 in New York City. (Photo by Images Press/IMAGES/Getty Images)
375250 01: Mid-1980's Playboy Mansion. Hugh Hefner and girlfriend Carrie Leigh at the Playboy Mansion.
Sondra Theodore and Hugh Hefner (Photo by Ron Galella/WireImage)
circa 1980: 'Playboy' magazine founder and publisher Hugh Hefner with 1980 Playboy Playmate of the Year, Canadian model and actor Dorothy Stratten. Stratten wears a strapless top and flowers in her hair. (Photo by Frank Edwards/Fotos International/Getty Images)
THE TOMORROW SHOW -- Pictured: (l-r) Playboy founder/publisher Hugh Hefner, journalist/Playboy covergirl Rita Jenrette at the Playboy Mansion -- Photo by: Paul Drinkwater/NBCU Photo Bank
Hugh Hefner and Carrie Lee attend the opening party for 'Private Lives' on October 13, 1983 at Madame Wu's Restaurant in Beverly Hills, California. (Photo by Ron Galella/WireImage)
Hugh Hefner and playboy bunnies are photographed October 29, 1985 at the re-opening of the Playboy Club in New York City. (Photo by Yvonne Hemsey/Getty Images)
Hugh Hefner and Carrie Lee attends the premiere of 'Beverly Hills Cop II' on May 19, 1987 at Mann Chinese Theater in Hollywood, California. (Photo by Ron Galella, Ltd./WireImage)
LOS ANGLES, CA - 1989: Playboy Magazine founder and publisher, Hugh Hefner, announces his engagement to Playmate of the Year Kimberly Conrad at a 1989 Los Angeles, California, press conference. Hefner and Conrad divorced in 2003. (Photo by George Rose/Getty Images)
368600 12: Hugh Hefner and friends, Jessica Paisley, left, Mandy Bentley and Sandy Bentley arrive for the 10th Anniversary celebration of the hit television show, 'Baywatch' on May 2, 2000 in Santa Monica, CA. The show has aired nearly 200 episodes since it first premiered in 1990. (Photo by Joe Thomas/Online USA)
Kimberly Conrad, Marsden Hefner, and Hugh Hefner during Christie Hefner Hosts Open House Gala for New Headquarters at Playboy Headquarters in Beverly Hills, California, United States. (Photo by Jim Smeal/WireImage)
Hugh Hefner and Kimberley Conrad in Photo Booth (Photo by Frank Trapper/Corbis via Getty Images)
Nancy Sinatra and Hugh Hefner attend Playboy Magazine Party on April 6, 1995 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
The Rembrandts, Yasmin Bleeth, Hugh Hefner & Playboy Bunnies (Photo by SGranitz/WireImage)
Hugh Hefner, wife Kimberly and their children during Premiere of 'Star Wars: Special Edition' In 1997 at Westwood in Westwood, CA, United States. (Photo by Magma Agency/WireImage)
Playmate Heather Kozar and businessman Hugh Hefner attend Playboy Announces Heather Kozar as the 1999 Playmate of the Year on April 29, 1999 at The Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
7/17/99 Los Angeles, Ca. Hugh Hefner Dancing With Playboy Gals At The Playboy Expo '99 & Playmate Reunion Held At The Pacific Design Center. (Photo By Brad Elterman/Getty Images)
7/16/99 Beverly Hills, CA Hugh Hefner, Shannon Tweed, and Diane Hunter (1954 Playmate) at the First-Ever Playboy Expo. The expo gave a chance for fans to meet centerfolds, celebrities, Bunnies, wirters, artists, photographers, and cartoonists. Photo Brad Elterman/Online USA, Inc.
CANNES, FRANCE: Playboy magazine president Hugh Hefner (C) poses with playmates 14 May 1999 on the steps of the Palais des Festivals before the screening of their movie 'Entrapment' in selection for the 52nd Cannes Film Festival. (ELECTRONIC IMAGE) (Photo credit should read PASCAL GUYOT/AFP/Getty Images)
BEVERLY HILLS, CA - APRIL 29: Hugh Hefner attends Playmate of the Year Press Conference on April 29, 1999 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
Brandi and Hugh Hefner during Madonna's new CD Music Party in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Madonna, Hugh Hefner & Playboy Bunnies (Photo by Kevin Mazur/WireImage)
WEST HOLLYWOOD, CA - DECEMBER 18: Playboy founder Hugh Hefner poses with unidentified model, Shauna Sand (2nd from L) and Holly Madison (R) during Barfly 5th year anniversary party on December 18, 2002 in West Hollywood, California. (Photo by David Klein/Getty Images)
Hugh Hefner and Playboy Playmates during Ben Stiller and Christine Taylor Host a Grand Classics Screening of 'Sweet Smell of Success' with YSL at the Playboy Mansion at Playboy Mansion in Beverly Hills, California, United States. (Photo by Donato Sardella/WireImage for Harrison & Shriftman)
Hiromi Oshima, Playboy Miss June 2004, Holly Madison, Hugh Hefner, Bridget Marquardt , Kendra Wilkinson, Sara Jean Underwood, Playboy Playmate of the Year 2007 and guest (Photo by Enos Solomon/FilmMagic)
Hugh Hefner and models during Hugh Hefner Inducted Into The Erotic Museum's Hall Of Fame at The Erotic Museum in Hollywood, United States. (Photo by Laurence Cottrell/FilmMagic)
(EXCLUSIVE, Premium Rates Apply) Carmen Electra and Hugh Hefner *EXCLUSIVE COVERAGE* (Photo by Michael Bezjian/WireImage for Playboy Enterprises)
Carmen Electra, top row far left, Hugh Hefner, center, The Girls Next Door and Playmates *EXCLUSIVE COVERAGE* ***Exclusive*** (Photo by Michael Bezjian/WireImage for Playboy Enterprises)
Hugh Hefner and girlfriends during The 21st Annual American Cinematheque Award Honoring George Clooney - Arrivals at Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by Jason Merritt/FilmMagic)
LOS ANGELES, CA - DECEMBER 16: Playboy founder Hugh Hefner attends a book signing of 'Mr. Playboy: Hugh Hefner and the American Dream' at Barnes N Noble bookstore on Tuesday December 16, 2008 in Los Angeles, California. (Photo by Byron Gamarro/Getty Images)
LAS VEGAS - MAY 15: (L-R) Model Hope Dworaczyk, Playboy founder Hugh Hefner and his girlfriend, December 2009 Playboy Playmate of the Month Crystal Harris, arrive at a party introducing Dworaczyk as the 2010 Playboy Playmate of the Year at the Rain Nightclub inside the Palms Casino Resort May 15, 2010 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
BEVERLY HILLS, CA - DECEMBER 10: Hugh Hefner and Pamela Anderson attend the Hugh Hefner book signing session at Taschen on December 10, 2009 in Beverly Hills, California. (Photo by Riccardo S. Savi/Getty Images)
LOS ANGELES, CA - DECEMBER 09: Playboy founder Hugh Hefner (L) and model Crystal Harris attend an event celebrating the expansion of Griffith Park at Lake Hollywood Park on December 9, 2010 in Los Angeles, California. (Photo by David Livingston/Getty Images)
LOS ANGELES, CA - OCTOBER 13: Hugh Hefner attends 'The Rum Diary' Los Angeles Premiere at LACMA on October 13, 2011 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
BEVERLY HILLS, CA - SEPTEMBER 19: Playboy Founder Hugh Hefner (C) arrives at the 2011 Ella Awards at The Beverly Hilton hotel on September 19, 2011 in Beverly Hills, California. (Photo by Paul Archuleta/FilmMagic)
BEVERLY HILLS, CA - AUGUST 07: (L-R) Hugh Hefner and Crystal Harris attend the Beverly Hills City Council and Playboy Enterprises ribbon-cutting ceremony for Beverly Hills Playboy World Headquarters on August 7, 2012 in Beverly Hills, California. (Photo by Tibrina Hobson/WireImage)
HOLLYWOOD, CA - JUNE 15: Publisher Hugh Hefner attends a press conference at the 35th Anniversary Playboy Jazz Festival - Day 1 at the Hollywood Bowl on June 15, 2013 in Hollywood, California. (Photo by Rodrigo Vaz/Getty Images)
Los Angeles, CA - OCTOBER 25: Hugh Hefner and Crystal Hefner attend Playboy Mansion's Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
LOS ANGELES, CA - JANUARY 16: Hugh Hefner (C) poses with Playboy Bunnies Playmate of the Year 2013 Raquel Pomplun (2nd L) and Miss December 2009 Crystal Hefner (2nd R) at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Rachel Murray/Getty Images for Playboy)
LOS ANGELES, CA - JANUARY 16: Cooper Hefner (L) and Hugh Hefner pose at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
LAS VEGAS, NV - FEBRUARY 20: Impersonator George Kane of Florida as Hugh Hefner presents an award during The Reel Awards 2017 at the Golden Nugget Hotel & Casino on February 20, 2017 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
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“Playboy’s Penthouse”

Hefner hosted the short-lived variety and talk TV show “Playboy’s Penthouse” in 1959, which was set up like a part at his apartment helped make the Playboy Bunnies famous. The show featured interviews with celebrities and featured names like Nina Simone and Ella Fitzgerald. It ended in 1961 after one season, but helped popularize Hef’s famous “Playboy lifestyle.”

Dick Gregory at the Playboy Club

With the success of Playboy, Hefner began growing a corporate empire. He founded the Playboy Club in Chicago and hired comedian Dick Gregory after seeing him perform at another club. The regular gig at the Playboy Club marked the break in Gregory’s career.

A reputation for journalism

In 1962, Playboy started to develop its reputation for journalism with the first Playboy Interview, in which author Alex Haley interviewed musician Miles Davis. Playboy became known for high-quality, revealing interviews with famous subjects over the subsequent years.

Arrest for selling obscene literature

Hefner was arrested and went to trial after being accused of selling obscene literature in 1963, after the publishing of an issue that featured nude photos of actress Jayne Mansfield. The jury was unable to reach a verdict, though, and the charges were eventually dropped.

44 PHOTOS
Playboy Magazine through the years
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Playboy Magazine through the years
An October 13, 2015 photo shows a November 2015 issue of Playboy magazine in Washington, DC. Playboy said Tuesday it will stop publishing nude photos in its iconic magazine for men, throwing in the towel in the face of rampant online pornography. AFP PHOTO/MANDEL NGAN (Photo credit should read MANDEL NGAN/AFP/Getty Images)
(Original Caption) 1/29/1962 -New York,NY -: Hugh M. Hefner, Editor and Publisher of Playboy, is shown with Cynthia Maddox, the blond cover girl on the February issue of his magazine, arriving by TWA superjet from Chicago. They are here to attend a party given by Ella Fitzgerald at the Basin Street East in honor of winners of the Playboys jazz poll.
British actor Sir John Mills (1908 - 2005) with his daughter, actress Hayley Mills, 1967. John's wife Mary Hayley Bell is between them. Hayley is holding a copy of 'Playboy' magazine. (Photo by David Farrell/Getty Images)
A rack of magazines at a stall in New York City, April 1986. Titles include 'Madamoiselle', 'New Look', 'Muscle & Fitness', 'Playboy', 'Cosmopolitan', 'MGF' and 'GQ'. (Photo by Barbara Alper/Getty Images)
Nancy Sinatra during Autographing Playboy Magazine & 1960's Album Reissue at Tower Records in New York City, New York, United States. (Photo by Ron Galella/WireImage)
3.17.98. Beverly Hills, California. Playboy magazine's founder and editor-in-chief Hugh Hefner at the Playboy Mansion
347380 15: Sable poses March 4, 1999 in New York City. Holder of the Women's Wrestling Championship title, Sable modelled for Guess Jeans and Pepsi prior to her latest shoot for Playboy Magazine. (Photo by Evan Agostini/Liaison)
THE TONIGHT SHOW WITH JAY LENO -- Episode 999 -- Pictured: (l-r) Fitness personality Richard Simmons during an interview with host Jay Leno on September 23, 1996 -- (Photo by: Margaret C. Norton/NBC/NBCU Photo Bank via Getty Images)
371916 01: Darva Conger, the bride who rejected her millionaire husband after their marriage on national television, poses for photographers June 29, 2000 at Tower Records in New York City. Conger was promoting the August 2000 issue of Playboy magazine, where she is featured on the cover and in the center layout. (Photo by George De Sota/Liaison)
368615 01: Playmate Of The Year, Jodi Ann Paterson Waves During A Press Conference At The Playboy Mansion April 27, 2000 In Holmby Hills, Ca. (Photo By Laurence Cottrell/Getty Images)
7/9/99 Los Angeles, CA. PMOY ''99, Heather Kozar at the Video Software Dealer's Association (VSDA) held at the Los Angeles Convention. Photo by David Keeler/Online USA, Inc.
Carmen Electra at a Playboy party to promote her December pictorial & her Playboy.com live chat, at Playboys New York City Headquarters. Oct. 30, 2000 (Photo: Evan Agostini / Getty Images)
388683 03: Playboy Playmate of the Year 2001 Brande Roderick poses with a blow-up of the magazine's cover sporting her image May 2, 2001 at One51 in New York City. (Photo by Diane L. Cohen/Liaison)
NEW YORK, UNITED STATES: Former Enron employees Cynthia Coghlan (L) of Toronto, Canada, Christine Nielsen (C) of Portland, OR, and Cary Lorenzo (R) of New York pose 27 June 2002 with a poster of Playboy Magazine in New York. The three posed with seven other former employees for Playboy magazine in the 'Women of Enron' August issue. Nielsen appears on the cover. AFP PHOTO/Stan HONDA (Photo credit should read STAN HONDA/AFP/Getty Images)
Johnny Fayva and Dave Navarro look at the new issue of Playboy featuring Carmen Electra (Photo by J. Vespa/WireImage)
Sarah Kozer, standing next to a giant Playboy magazine cover with her on it, at the 2003 Playboy Playmate of the Year. (Photo by Frank Trapper/Corbis via Getty Images)
BEVERLY HILLS, CA - APRIL 24: Playmate of the Year for 2003 Christina Santiago is congratulated by Publisher Hugh Hefner at the Playboy Mansion April 24, 2003 in Beverly Hills, California. 'American Idol's' Ryan Seacrest announced the 2003 Playmate of the Year, who will appear in the June issue with 'Joe's Millionaire's' Sarah Kozer on the cover. (Photo by David Klein/Getty Images)
HOLLYWOOD, CA - JUNE 12: Model Nikki Ziering (R) and actor Jason Biggs attend the release party for Ziering's July Playboy Magazine cover on June 12, 2003 at The Nacional club in Hollywood, California. (Photo by Lucy Nicholson/Getty Images)
UNITED STATES - AUGUST 13: Playboy magazine featuring an article on Google is seen at a newsstand in Manhattan, New York on Friday August 13,2004. (Photo by Jennifer S. Altman/Bloomberg via Getty Images)
JAKARTA, INDONESIA: A hawker holds a copy of the second issue of Indonesian edition of US adult magazine Playboy while looking for customers in downtown Jakarta, 07 June 2006. A defiant second issue of the magazine hit Jakarta's streets 07 June, produced from its new headquarters on the mostly Hindu resort island of Bali. The edition is the first to reappear after violent Muslim hardliners forced the closure of the publisher's Jakarta office in April and contained no commercial advertisements. AFP PHOTO/Jewel SAMAD (Photo credit should read JEWEL SAMAD/AFP/Getty Images)
Tricia Helfer, Cylon Number 6 from 'Battlestar Galactica' (Photo by Albert L. Ortega/WireImage)
New York, UNITED STATES: United States Olympic gold medal swimmer Amanda Beard poses with her Playboy Magazine cover during the opening day of the 2007 Licensing International Expo at the Jacob Javits Convention Center 19 June 2007 in New York. The show that runs until 21 June showcases the world's brand and property marketplace. AFP PHOTO/TIMOTHY A. CLARY (Photo credit should read TIMOTHY A. CLARY/AFP/Getty Images)
ATLANTIC CITY, NJ - FEBRUARY 16 Kendra, one of the stars of 'The Girls Next Door,' and current Playboy Cover Girl signs a cover of Playboy Magazine for a fan as shesappears at The Pool in Harrah's Resort on February 16, 2008 in Atlantic City, New Jersey. (Photo by Donald Kravitz/Getty Images)
BURBANK, CA - AUGUST 18: Actress and current Playboy model Christa Campbell tries to cover up her new Playboy magazine photo spread (not entirely successfully!) at an autograph party for the new graphic novel '2001 Maniacs', held at the Dark Delicacies bookstore on August 18, 2007 in Burbank, California. (Photo by Michael Tullberg/Getty Images)
The Venezuelan edition of Playboy magazine with a picture of Argentine policewoman Maria de Lujan Telpuk on its cover is on display at a kiosk in Caracas, on March 13, 2008. Telpuk is the police officer who in August 2007 found 800,000 US dollars inside a suitcase which Venezuelan businessman Guido Antonini Wilson was illegally trying to get into Argentina, apparently, according to investigations, for the electoral campaign of current president Cristina Fernandez de Kirchner. AFP PHOTO/Juan BARRETO (Photo credit should read JUAN BARRETO/AFP/Getty Images)
NEILL J. SCHUTZER/�2009 RAMEY PHOTO LOS ANGELES 8/13/09 HEIDI AND SPENCER WITH THE NEW PLAYBOY MAGAZINE. NJSBPE (Photo by Philip Ramey/Corbis via Getty Images)
Issues of Playboy and Penthouse magazines are arranged for a photo in New York, U.S. on Thursday, July 15, 2010. FriendFinder Networks Inc., the owner of Penthouse, said it will offer $210 million to acquire Playboy Enterprises Inc., challenging a bid from Hugh Hefner to take the company private. Photographer: Jonathan Fickies/Bloomberg via Getty Images
NEW YORK, NY - SEPTEMBER 14: Playboy magazine on seat at the The Blonds Spring 2012 fashion show during Mercedes-Benz Fashion Week at Center 548 on September 14, 2011 in New York City. (Photo by Cindy Ord/Getty Images)
MEXICO CITY, MEXICO - DECEMBER 14: Daiana Guzman presents the cover of Playboy magazine edition December 2011, 2011 in Mexico City, Mexico. (Photo by Angel Delgado/Clasos.com/LatinContent/Getty Images)
MEXICO CITY, MEXICO - MAY 07: Actress Erika Garcia attends the Playboy Mexico Magazine May 2012 issue photo call at La Mansion on May 7, 2012 in Mexico City, Mexico. (Photo by Victor Chavez/WireImage)
A picture taken on March 6, 2013 shows the first Hebrew edition of the iconic men's magazine Playboy in Israel following the magazines debut in the Holy Land at a shop in the Mediterranean coastal city of Tel Aviv. The articles -- which will be read from right to left, like Arabic -- would be a mix of original Israeli writing and translations from US and foreign editions, spokeswoman Danielle Peters told AFP. AFP PHOTO / JACK GUEZ (Photo credit should read JACK GUEZ/AFP/Getty Images)
MEXICO CITY, MEXICO - SEPTEMBER 11: Colombian adult film actress Esperanza G�ez (r) poses with a fan while she signs copies of Playboy Mexico magazine september 2014 cover model at Galerias Plaza de las Estrellas on September 11, 2014 in Mexico City, Mexico. (Photo by Victor Chavez/WireImage)
Magazine issues from the period are on display at ?Playboy Architecture, 1953-1979', an exhibit hosted by the German Architecture Museum on the Museumsufer in Frankfurt, Germany, 08 April 2014. The exhibit shows the central role of the magazine during the avant-garde architecture from the fifties up to the end of the seventies, when the magazine presented innovative and visionary architectural designs, becoming one of the most important mediums of avant-garde design. (Photo by Horacio Villalobos/Corbis via Getty Images)
Norwegian model Christina Gjerdrun, 23, launches the first copy of Playboy magazine's Norwegian edition in Oslo, November 19. Gjerdrum is featured as Miss December and January in the magazine. NORWAY PLAYBOY
Among the garbage and equipmente, a large collection of Playboy magazines - with issues from as early as 1991 - was found stored in an office. USP public relations says it belongs to the students; their representative say that they didn't even know it existed Photo: Gustavo Basso/NurPhoto (Photo by NurPhoto/Corbis via Getty Images)
UNITED STATES - AUGUST 13: Playboy magazine featuring an article on Google is seen at a newsstand in Manhattan, New York on Friday August 13, 2004. (Photo by Jennifer S. Altman/Bloomberg via Getty Images)
MEXICO CITY, MEXICO - MAY 02: Tracy Saenz attends the Playboy Mexico magazine may 2016 issue photocall at Fiebre de Malta on May 2, 2016 in Mexico City, Mexico. (Photo by Victor Chavez/WireImage)
LOS ANGELES, CA - JUNE 23: Playmate Jaime Faith Edmondson celebrates the release of Playboy magazine's 'The Freedom Issue' at No Vacancy on June 23, 2016 in Los Angeles, California. (Photo by Rich Polk/Getty Images for Playboy)
LOS ANGELES, CA - JUNE 23: Playmates Heather Rae Young and Hiromi Oshima celebrate the release of Playboy magazine's 'The Freedom Issue' at No Vacancy on June 23, 2016 in Los Angeles, California. (Photo by Rich Polk/Getty Images for Playboy)
MEXICO CITY, MEXICO - JULY 04: Natalia Subtil shows the magazine during the launching of the new Playboy at Aida Restaurant on July 04, 2016 in Mexico City, Mexico. (Photo by Hector Vivas/LatinContent/Getty Images)
Publisher director of the controversial Indonesian version of Playboy magazine, Erwin Arnanda, shows the first edition in Jakarta April 6, 2006. The local version of Playboy magazine will go on sale on Friday despite growing protests from conservative Muslim groups and nationalist politicians. REUTERS/Dadang Tri
The December issue of Playboy magazine features Olympic gold medalist ice skater Katerina Witt on the cover. Witt, 33, posed nude for a 10-page pictorial in the magazine. SJO/SV/ME
Playboy magazines are displayed on a news stand in New York, U.S., on Thursday Nov. 12, 2009. Playboy Enterprises Inc., the men's magazine publisher, is in talks to sell itself to Iconix Brand Group Inc., according to two people close to the situation. Photographer:Rick Maiman/Bloomberg via Getty Images
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“Playboy After Dark”

In 1969, Hefner hosted another variety show similar to “Playboy’s Penthouse,” but with a greater focus on rock and roll. The show featured guests such as James Brown and Milton Berle, but only ran until 1970.

Stepping away from the empire

Hefner suffered a small stroke in 1985, which caused him to re-evaluate the Playboy lifestyle. He named his daughter chair and CEO of the Playboy empire, but stayed on at the magazine as editor-in-chief. After that, Hefner turned much of his attention to philanthropic efforts.

“The Girls Next Door”

In 2006, Hefner starred in “The Girls Next Door,” a reality show about the daily lives of his three girlfriends at the time, Holly Madison, Kendra Wilkinson and Bridget Marquardt, who lived with him in the Playboy Mansion. The show ran for six seasons and 90 episodes, ending in 2010.

Razzie nomination

After playing himself in the 2009 movie “Miss March,” Hefner was nominated for a Razzie award for “Worst Supporting Actor.” He joked about the nomination on his Twitter account, saying, “Maybe he didn’t understand the character.”

Read original story 10 Major Moments from Hugh Hefner’s Career (Photos) At TheWrap

38 PHOTOS
Celebrities react to Hugh Hefner's death
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Celebrities react to Hugh Hefner's death
American Icon and Playboy Founder, Hugh M. Hefner passed away today. He was 91. #RIPHef https://t.co/tCLa2iNXa4
A great man, entrepreneur and innovator. Your legacy lives on. #Hef https://t.co/36cRzlUPRw
RIP #Hef Thank you for being a revolutionary and changing so many people's lives, especially mine. I hope I made y… https://t.co/6Nz7oqYdfj
Hugh Hefner was a GIANT in publishing, journalism, free speech & civil rights. He was a true original, and he was m… https://t.co/8ThS9oAAGm
RIP to the legendary Hugh Hefner! I’m so honored to have been a part of the Playboy team! You will be greatly missed! Love you Hef! Xoxo
Hugh Hefner was a strong supporter of the civil rights movement. We shall never forget him. May he Rest In Peace. https://t.co/oL3lKLZRQ5
So sad to hear the news about @HughHefner. 😢 #RIPHef https://t.co/IQiEYhMfvf
1st met him months B4 #SW opened-Expected stereotyped swinger/wildman not the kind-thoughtful loyal friend he alway… https://t.co/RPOBh7ZuxE
I met Hugh Hefner at the Playboy mansion. He was very nice to my mom. Don't ask. #RIPHef
I had a number of great conversations and with Hugh Hefner. Was such an interesting man. True legend. What an end of an era!
I just found out @hughhefner died. Thank u for the time together, 2 covers& artistic freedom on my second shoot. you believed in my vision
Goodnight Playboy.
RIP @hughhefner 💛 thank you for making me part of the Playboy family. Sending lots of love and prayers to @crystalhefner
RIP HF. Few did more for writers, inc myself, breaking boundaries and helping Lenny fight for his 1st Amend Right… https://t.co/tj620dcXa1
Hugh Hefner put me in Playboy & ignited my career. I am forever indebted, Hef. You will forever live on as an icon of epic proportions. #RIP
RIP to the OG #HughHefner 🙏🏽 https://t.co/AVXwKU1V4A
We love you #hef #HughHefner https://t.co/gr5DXSH22D
Trailblazer. Icon. An American institution! Rest in that big grotto in the sky, Hugh Hefner! https://t.co/9rKnQERPgw
Rest In Peace Hugh Hefner. 🐇Dr. Buss treasured your friendship. You lived life your way. #Maverick #Playboy https://t.co/gdVZNGtiBW
@hughhefner ..when I did playboy he spoke words to me that affected my direction. he was a man the room would stop for when he entered #rip
RIP HUGH HEFNER
Today the world lost a legend. #HughHefner started my career. For 22 yrs I got to wish him happy new year at his ma… https://t.co/vmkyGpipfx
Wow...just read the news. Rest In Peace Hugh Hefner. Your legacy and soul shall live on!
RIP Hugh Hefner I went to so many of his parties at the Playboy mansion it was legendary you will never be forgotten
Rest in peace #HughHefner - he will forever be remembered as the Hollywood legend who lived life to the fullest.
R.I.P. to the legend Hugh Hefner https://t.co/0WopDrAH1h
If you were raised without a mom Hugh Hefner probably changed your life. Champion of great writing & freedom of speech & always kind to me.
RIP What a life!!!!
Hefner. A giant of cultural influence.
RIP to a true pioneer! Playa for life! We will miss you. #Playboy https://t.co/3G97CQa5d0
Thank you, Hef, for Playboy. And thank you for what you did for me. You've left such an impact on the world...you'l… https://t.co/4NYB5IZ7Jy
We’ve lost a true explorer, a man who had a keen sense of the future. We learned a lot from you Mr. Hefner. #HughHefner
One of the nicest men I've ever known. Godspeed, Hugh Hefner. https://t.co/457cchqskO
RIP my friend. You changed the world.
As per his wishes, Hugh Hefner’s body will be left in a fort in the woods for other kids to find & pass around.
Hugh Hefner put me in Playboy & ignited my career. I am forever indebted, Hef. You will forever live on as an icon of epic proportions. #RIP
RIP hef. You were always sweet to me on movie nights at the mansion. Love to you @crystalhefner xo #RIPHef
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