Photos: Hugh Hefner through the years

In this 2007 photo, Hugh Hefner smiles while signing copies of the Playboy calendar and "Playboy Cover To Cover: The 50's" DVD box set in Los Angeles. The Playboy founder died at age 91, his company announced Wednesday, Sept. 27, 2017.

FILE - In this June 20, 1961 file photo, Playboy magazine publisher Hugh Hefner poses with "bunny-girl" hostess Bonnie J. Halpin at Hefner's nightclub in Chicago. Playboy founder and sexual revolution symbol Hugh Hefner died on Wed., Sept. 28, 2017 at age 91.

FILE - In this April 26, 2010 file photo, Hugh Hefner, left, and Crystal Harris arrive at the premiere of Iron Man 2 at the El Capitan Theatre in Los Angeles. Hefner and Harris obtained a marriage license in Beverly Hills, Calif. on Tuesday Dec. 4, 2012, roughly a year-and-a-half after the centerfold called off the couple's previous engagement.

FILE - In this Oct. 13, 2011 file photo, American magazine publisher, founder and Chief Creative Officer of Playboy Enterprises, Hugh Hefner at his home (aka Playboy Mansion) in Beverly Hills, Calif. Playboy will no longer publish photos of nude women as part of a redesign of the decades-old magazine, according to a news report Monday, Oct. 12, 2015. Executives for the magazine company told The New York Times that the change will take place in March 2016. Playboy editor Cory Jones contacted current editor in chief Hefner recently about dropping nude photos from the print edition and he agreed, the Times reported.

"Playboy founder Hugh Hefner, second from left, poses for a photo with director Brigette Berman, second from right, and three companions ahead of the screening of the film ""Hugh Hefner: Playboy, Activist and Rebel"" by two companions at the Toronto International Film Festival on Saturday Sept. 12, 2009 in Toronto.

Playboy Chairman & CEO Christie Hefner, and her father Playboy founder Hugh Hefner, hold the gavel that closes trading on the New York Stock Exchange after they rang the closing bell, Wednesday Dec. 3, 2003. Playboy, which listed on the exchange Dec. 20, 1997, is celebrating its 50 anniversary.

Playboy Magazine founder Hugh Hefner sits with January, 2000 Playmates Carol, left, and Darlene Bernola, Thursday, Dec. 2, 1999, at his home in the Holmby Hills area of Los Angeles. The twins were chosen from more than 18,000 candidates who interviewed with Playboy.

FILE - In this May 7, 1977, file photo, Playboy magazine founder Hugh Hefner talks about his coming late night TV show, Playboys Playmate Party, Los Angeles. Hefner has died at age 91. The magazine released a statement saying Hefner died at his home in Los Angeles of natural causes on Wednesday night, Sept. 27, 2017, surrounded by family.

Playboy Founder Hugh Hefner speaks with a television news crew in front of the Playboy Mansion Haunted House in Los Angeles, Calif. on Friday, Oct. 27, 2006.

Playboy founder Hugh Hefner poses with Holly Madison, right, Bridget Marquardt, and Kendra Wilkinson, left, at an event promoting the November issue of Playboy Tuesday, Oct. 11, 2005 in New York. The women are the three stars of the E! cable television show "The Girls Next Door" and are featured in the magazine.

Playboy founder Hugh Hefner, who's on the brink of 80, looks back at copies of Playboy magazine, Tuesday, Oct. 11, 2005 in New York. Hefner and the three stars of the E! cable television show "The Girls Next Door," who are featured in the magazine, were autographing copies of the magazine.

Hugh Hefner, center, talks with CBS News correspondent Bryant Gumbel, right, and Gumbel's friend Hilary Quinlan at a party thrown by Hefner welcoming the news media in town to cover the Democratic National Convention, at the Playboy Mansion Saturday, Aug. 12, 2000, in Los Angeles' Holmby Hills district.

** FILE ** Hugh Hefner arrives at the American Film Institute Life Achievement Award event honoring Al Pacino in Los Angeles in this June 7, 2007, file photo.

Playboy magazine founder Hugh Hefner laughs with reporters before a ceremony Tuesday, April 11, 2000, honoring Hefner with a street sign on Chicago's near North Side. The honorary street sign came under fire by the City Council who rejected the proposal but the decision was reversed during a meeting the council's finance committee the next day. Hefner his flanked by his twin girlfriends Mandy, left, and Sandy Bentley, to his right.

FILE--Hugh Hefner poses in this Sept. 26, 2000 file photo, at the Playboy Mansion in Los Angeles, Calif. Playboy has been awarded the rights to the Internet domain name hughhefner.com in a U.N. panel ruling released Wednesday, May 23, 2001. The adult entertainment empire brought the case against the Good Samaritan Program of Owings Mills, Md., which had registered the name.

American icon and Playboy founder Hugh M. Hefner has died, said an announcement released on Wednesday, Sept. 27, 2017.

FILE - In this March 1970 file photo, Hugh Hefner, left, and girlfriend Barbi Benton, center, are served by Playboy Club Bunny Cheri upon their arrival at La Guardia aboard the Big Bunny, Heffner's jet, in New York. Playboy magazine founder and sexual revolution symbol Hefner has died at age 91. The magazine released a statement saying Hefner died at his home in Los Angeles of natural causes on Wednesday night, Sept. 27, 2017, surrounded by family.

FILE - In this April 5, 2007 file photo, Hugh Hefner poses for a photo at the Playboy Mansion in Los Angeles. Playboy magazine founder and sexual revolution symbol Hefner has died at age 91.