Playboy Founder Hugh Hefner Dies At 91, But His Chicago Legacy Remains

CHICAGO, IL — Hugh Hefner died peacefully at his home, the Playboy Mansion, near Beverly Hills Wednesday. The silk-robed legend will be buried next to Marilyn Monroe. He was 91 years old.

One of his most famous quotes:

"Life is too short to be living somebody else's dream."

And his dream began in Chicago. He was born in Michael Reese Hospital to devout Methodist parents Grace and Glenn Hefner. Hugh Hefner's younger brother Keith was born 3 years later. The family lived on N. New England Ave. in the Galewood neighborhood on the Northwest Side.

Watch: Hugh Hefner, The Original Playboy, Dies At 91

In a quote from a Playboy interview in 1974, Hefner said he began disagreeing with his family's religion from a young age.

"I began questioning a lot of that religious foolishness about man’s spirit and body being in conflict, with God primarily with the spirit of man and the Devil dwelling in the flesh,” he explained.

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And rebel he did, becoming one of the most controversial figures of the 20th century. The legend of "Hef" grew as he helped ignite the sexual revolution of the 1960s, and both infuriated and inspired the masses. He founded Playboy in 1953 with $600, and from there the magazine ballooned into a multimillion-dollar empire with cocktail clubs, TV shows, and festivals.

• 5 Things To Know About Hugh Hefner, Playboy Extraordinaire

When Hefner was only 8 years old, he launched a school newspaper in his school, Sayre Elementary. In a quote from the Chicago Tribune, he said he thrived during his years at Steinmetz High School:

“The best time of my life before Playboy was my last two years at Steinmetz. It was a coming-of-age time. It was the first time I went steady. I was a class leader, writing and performing in plays and shows, working on the paper. The things I enjoyed were the things between classes.”

After graduating from high school, Hefner joined the U.S. Army as a writer for a military newspaper during World War II.

After the war, Hefner attended the University of Illinois at Urbana Champaign, and received a Bachelor of Arts in psychology and a double minor in creative writing and art. He also took graduate courses in sociology at Northwestern University, but dropped out.

Hefner began working as a copywriter for Esquire, but left after he was denied a $5 raise. And from there it all began. He took out a mortgage, and launched Playboy. The first magazine showcased Marilyn Monroe from her 1949 nude calendar shoot, and sold more than 50,000 copies.

The photo above depicts Hefner joking with women in his $400,000 Chicago apartment in 1961. But that wasn't his only glamorous Chicago digs—from the 1960s to the late 1980s, Michigan Avenue was the home of the Playboy Enterprises headquarters, in what's now known as the Palmolive Building.

In 2015, Vince Vaughn listed his 12,000-square-foot penthouse in the building for $13.9 million, featuring a 360-degree view. The apartment also featured Hefner's old office, a screening room, two kitchens, and four bedrooms.

For decades, Hefner's reputation stirred up controversy, as he bedded hundreds of young women and promoted porn. Many have called him a 'relic' of a sexist era, but others have celebrated his success in breaking up much of the conservative values surrounding sex in the 1950s and early 1960s.

Hefner's younger brother Keith was a longtime executive with Playboy. Like his older brother, he loved the company of younger women, and was featured on the reality TV show The Girls Next Door, about Hugh's life with his three girlfriends.

Keith Hefner died last year at his Beverly Hills home before Hugh's 90th birthday.

"My folks were raised pure prohibitionist," Hefner told the Hollywood Reporter in 2011. "They were very good people, with high moral standards—but very repressed. There was no hugging and kissing in my home."

Hefner certainly indulged in his share of hugging and kissing—and much more—over his lifetime. But he said his puritanical roots as a child in Chicago made him who he was, and inspired his legacy.

Main photo via Frazer Harrison/Getty Images