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Hugh Hefner's Chicago: The Neighborhoods That Helped Make The Man

By DNAinfo Staff | September 28, 2017 8:38am | Updated on September 28, 2017 9:38am
 Chicago's Playboy Club was founded Feb. 29, 1960. Hugh Hefner is shown with some of the Playboy Bunnies.
Chicago's Playboy Club was founded Feb. 29, 1960. Hugh Hefner is shown with some of the Playboy Bunnies.
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DOWNTOWN — Playboy founder Hugh Hefner died Wednesday in California at age 91. But it was Chicago that helped shape him into what he was.

Here are some locations that helped make the man:

• Hefner was born at Michael Reese Hospital on the South Side and grew up at 1922 N. New England Ave. on the Northwest Side. His father, Glenn, was an accountant; his mother, Grace, was a homemaker.

"I was the kid in the neighborhood who always created the games," he said on a visit back in 1992.

"When I was a child, the street lights were still gas. And you got your milk and coal and ice delivered by horse-drawn wagons. And at night, you could hear the train whistles. One of the loveliest sounds in the world."

 Chicagoans paid their respects to the legendary publisher at the original Playboy Mansion in the Gold Coast. 
Makeshift Hugh Hefner Memorial At Playboy Mansion
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He would attend Sayre School, 1850 N. Newland Ave.

• Hefner went to Steinmetz High School, 3030 N. Mobile Ave., which he would later describe as the place where he became "the teenager that I wanted to be."

In "Mr. Playboy," author Steven Watts says Hefner became the leader of a group of friends, and at 17, "created the persona of an imaginative, romantic figure" which "became a template for his life."

He started referring to himself as "Hef" and once described his character as "a lanky Sinatra-like guy with a love for loud flannel shirts and cords, and jive for music."

He was in the Class of 1944.

In June 1949, Hefner married classmate Mildred Williams and their 10-year marriage produced two children: Christie in 1952 and David in 1955.

In 2016, Hefner sent the school's newspaper, the Steinmetz Star, a pledge of $37,500 over five years (or $7,500 a year) to preserve the paper's more-than-80-year tradition of printing after Chicago Public Schools officials announced the Star's print edition would have to cease because of cost concerns.

RELATED: Hugh Hefner Saves Embattled School Newspaper of His High School Alma Mater

Playboy came out of a key moment in Hefner's life that occurred Downtown.

"About a year before the first issue of Playboy, I was standing on the Michigan Avenue bridge, looking out at the river, a bit teary-eyed, thinking, “Where is my life going?” " he told NBC5.

"I’d recently attended a high school alumni revue that reminded me of all of the good times I had as a kid. I’d been a real school leader and done all sorts of creative things — shows and musicals. But I had put all of those dreams away. In the weeks that followed, I simply decided, 'F--- it! I’m going to create the magazine I want to create no matter what.' And I did."

• In 1966, he moved the magazine's offices into the Palmolive Building at 919 N. Michigan Ave.

It later became the Playboy Building, known for its large sign and blue beacon on top.

"When Hugh Hefner was growing up on Chicago’s West Side he used to see the beacon sweep across the sky. He wrote that it represented Gatsby-esque glamour to him. After his own rise to fame and fortune he bought the building and renamed the light the Bunny Beacon," said historian and WTTW host Geoffrey Baer.

The company left Chicago in 1989.

• Hefner lived in a mansion in the Gold Coast, throwing legendary parties. The home, at 1340 N. State Parkway, feaured a brass plate hung on the door reading Si Non Oscillas, Noli Tintinnare — Latin for "If you don't swing, don't ring." 

It had a pool in the basement, which could be accessed by a fire pole from the floor above, and a bowling alley. Guests included some of the biggest stars of the day.

He lived there from 1959 to 1974, originally buying it for $400,000. It later became a dormitory for the School of the Art Institute and after that was converted into condos.

RELATED: Live in the Original Playboy Mansion for $3.4 Million

• The first Playboy Club was at 116 E. Walton St. The magazine regularly ran photos of it and described it as a place for "urban fellows who are less concerned with hunting, fishing and climbing mountains than with good food, drink, proper dress and the pleasure of female company."

When it opened in 1960, drinks were $1.50 each, pricey at the time. Hefner originally wanted the waitresses to wear nighties, but switched to bunny costumes. 

"A member showed his key to the Door Bunny, his name was posted in the directory board in the lobby, and he was free to roam throughout the club," Kathyrn Leigh Scott wrote in "The Surprising Inside Story of the Playboy Clubs." 

Members were not, however, allowed to date the bunnies.

Open until 4 a.m. the club "became the most popular nightclub in town."

“The original motivation for the Chicago Playboy Club was to have a place to hang out with friends," Hefner told DNAinfo Chicago in 2016. "My initial concern was how to recreate for club members the fantasy that was reflected in the pages of the magazine. As it turned out, we put it all together and they brought the fantasy with them.”

RELATED: The Very First Playboy Club Opened On Leap Day In Chicago