But others will celebrate the man known as "Hef" as an American icon who promoted black artists, writers and athletes, tackled social issues like segregation and advocated for the LBGT community.
"I would like to be remembered as somebody who has changed the world in some positive way, in a social, sexual sense, and I'd be very happy with that," Hefner once told CNN.
His civil rights advocacy was chronicled in a 2009 documentary, "Hugh Hefner: Playboy, Activist, Rebel."
The documentary recounted how in 1955 Hefner published, "The Crooked Man," a science fiction story in which heterosexuals were persecuted in a homosexual world. The Charles Beaumont story had been rejected by other publications.
"If it was wrong to persecute heterosexuals in a homosexual society, then the reverse was wrong, too," Hefner wrote to outraged readers, according to the LBGT magazine the Advocate.
In the documentary, football great Jim Brown called Hefner "one of the many human beings in that era that fought against injustice."
Playboy magazine regularly carried lengthy interviews with high-profile African-Americans like the Rev. Martin Luther King Jr., Muhammad Ali and Malcolm X.
The popular "Playboy Interview" debuted in 1962 with jazz legend Miles Davis. It was written by Alex Haley, then a young contributor who would later write "Roots: The Saga of an American Family."
Hefner's television series, "Playboy's Penthouse," was among the first programs to mix groups of black and white performers and audience members, according to his company. He took a stance against segregation by integrating Playboy Clubs in Miami and Louisiana.
"I knew I could do the other half of what I'm really all about, which is social justice," Hefner told Larry King in 2010. "It wasn't simply race. It had to do with sexual prejudice and it had to do with drug prejudice."
The civil rights activist the Rev. Jesse Jackson praised Hefner on Twitter late Wednesday as "a strong supporter of the civil rights movement."
"We shall never forget him," Jackson wrote.
The son of an accountant and a teacher, both conservative Protestants from Nebraska, Hefner over the years spoke out against sodomy laws. He told interviewers he supported same-sex marriage.
"I'm a human rights activist," Hefner said in a 1994 Advocate interview
when asked if he considered himself a gay rights activist.
Referring to archaic sodomy laws in some states, Hefner told the Advocate: "If the pursuit of happiness has any meaning at all as it is written in the Constitution, the government's intruding into one's bedroom, into personal sexual behaviors, is as unconstitutional as anything can be."
Model and actress Caroline "Tula" Cossey was outed as a transgender woman by a tabloid after she appeared in the 1981 James Bond movie "For Your Eyes Only," according to her IMDb bio. Playboy later made her the magazine's first openly transgender model.
"R.I.P Hugh Hefner Thank u 4 allowing me 2 share my story & 4 ur support & platform that helped my campaign 4 trans rights and visibility," Cossey wrote on Twitter.
In a statement, Cooper Hefner, chief creative officer of Playboy Enterprises, said: "My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom."