All it took was the purchase of a Marilyn Monroe photo from a suburban Chicago calendar company.
That’s the spark Playboy creator Hugh Hefner needed to complete his vision for a gentleman’s publication, which he hoped would have mass appeal — not just for its provocative photos — but also its witty, thought-provoking articles.
Hefner died at the age of 91 in 2017.
Hefner’s childhood home
1922 N. New England Ave., Chicago
As a boy, Hefner published a typewritten newspaper and sold copies for a penny each in his childhood neighborhood. In the February 1994 Chicago Tribune magazine, Hefner reflected on his time growing up on the city’s Northwest Side and on the details of a visit he made there in October 1992.
“I had a very happy and very inventive childhood in my old Chicago neighborhood on the Northwest Side, between Oak Park Avenue and Harlem. The closest busy street to us was Grand Avenue, which led straight into the heart of the city.”
— Hefner (Chicago Tribune, Feb. 20, 1994)
Steinmetz College Prep, Hefner’s high school
While a student at the school (known as Steinmetz High School when he graduated in 1944), Hefner founded a school paper, wrote and drew cartoons. He also served as student council president, according to the school’s website.
He visited the school in 2010 and made a $7,500-a-year, five-year commitment to keep printing its newspaper. He renewed that commitment in 2016.
“When I walked the streets of my old neighborhood during that October (1992) visit, it was magic. I went back to Steinmetz High School, I noted that they still had on the wall the honor roll of the boys who’d served in World War II, with my name and those of my classmates on it. I really felt I could walk right back into my childhood.”
— Hefner (Chicago Tribune, Feb. 20, 1994)
The apartment where Hefner produced the first copy of Playboy
In an April 21, 2012, editorial in the Chicago Tribune, Hefner said he started the magazine with $8,000 raised through selling his furniture and borrowing from family and friends.
His debut issue, produced at his apartment’s kitchen table, featured a Marilyn Monroe photograph purchased from a suburban calendar company. It didn’t include a cover date since Hefner was unsure when or if he would be able to produce another. He described his enjoyment in watching people pick up the magazine from newsstands in December 1953.
By 1971, when Playboy Enterprises went public, the magazine was selling more than 7 million copies a month. In 2017, the magazine had about 800,000 subscribers.
“I like to think the magazine’s presence provided the city with an edge, a reminder to the rest of America that the first steps of the sexual revolution took place at a card table at 6052 S. Harper Ave., ran wild in a State Street mansion and grew into a global presence on Michigan Avenue visible to anyone driving down Lake Shore Drive.”
— Hefner (Chicago Tribune, April 21, 2012)
The original Playboy mansion
Hefner purchased the mansion in 1959 for $400,000 with plans to build a pool in the basement. The city would only allow it after Hefner convinced officials it was for personal, not commercial, use.
A spread in the March 5, 1961, Chicago Tribune magazine described how Hefner turned a car-service area into a lounge, which was positioned slightly lower than the bottom of the pool: ” … in the manner of an aquarium, permitting a view of the swimmers and pool activities.”
His office was in his bedroom, which later included a 100-inch-diameter circular bed described as having “more controls and more gadgets than a Boeing 747.” Other Hefner additions include sun and steam rooms, a bowling alley, game room, a closed-circuit television security system and a full-size movie projection system.
House guests were common and included cartoonist Shel Silverstein, comedian Bill Cosby, all five Rolling Stones and actor Warren Beatty. Hefner lived on the second floor of the mansion, and the third and fourth floors would become Bunny dormitories, where rent was $50 a month. The rules were strict: No male visitors and no liquor unless Hefner offered it.
Hefner was arrested here in 1963 on an obscenity charge — but not before police allowed him to change from a pink cardigan sweater, white sports shirt and dark slacks into a suit.
After purchasing the Los Angeles mansion in 1971, Hefner spent less time in Chicago. In August 1984, Playboy Enterprises leased the Chicago mansion to the School of the Art Institute for five years at $10 a year. (Hefner had taken a figure drawing class at the school.) Renamed Hefner Hall, it served as a student dormitory until 1990.
A real-estate firm purchased the mansion from the school in 1993 and converted it into condos.
“Hugh M. Hefner, 33, publisher of Playboy magazine, told the city zoning board of appeals last week that he needs a swimming pool in the basement of his near north side home to help him relax from the rigors of his job.”
— Chicago Tribune, March 27, 1960
First Playboy office
Located across the street from Holy Name Cathedral, this site served as the magazine’s first office. Hefner also lived there.
A different building now stands at the site.
“On a nostalgic drive the other day, Hugh Hefner went back to the first place where he worked and lived while starting Playboy (11 E. Superior St). Hef rang the doorbell. The same landlady answered the door, invited him in, and showed him the premises.”
— Chicago Tribune, Feb. 3, 1974
Where the magazine was printed
W. F. Hall Printing Co. was the principal printer for Playboy for 30 years, until the company lost the contract in 1985. Printing of Playboy moved out of state. That forced the printer to lay off 750 employees and a building leased close down its operations at that site.
Today, The Hall Plaza, which includes a Walmart, occupies the site.
First Playboy Club
Known as the Playboy Key Club, it opened on Leap Day (Feb. 29) 1960, in a building leased from Chicago Bulls and Blackhawks owner Arthur Wirtz.
The club was inspired by another Chicago establishment called the Gaslight Club, which required its members to carry a key for entry and featured a waitstaff of women decked out in sequin-trimmed velvet corsets and little else.
Ads in the Chicago Tribune and other publications said Playboy was offering a “Great opportunity for the 30 most beautiful girls in Chicagoland” to work as Playmates at the club. Nearly 17,000 people visited it in its first month of operation.
The Chicago club moved over the years, ending up at Clark Street and Armitage Avenue, before finally closing for good in 1986.
“And the Playboy Key club, at the site of the Cameo and Chase on Walton place, will open with Mabel Mercer as its first starring act.”
— “On the Town” column (Chicago Tribune, Feb. 28, 1960)
Filming location for “Playboy’s Penthouse”
Filming for Playboy’s first television show, “Playboy’s Penthouse,” started in 1959 at WBKB-TV studios (now WLS-TV Ch. 7) and continued for two years. It included appearances by singer Ella Fitzgerald, author Carl Sandburg and comedian Lenny Bruce with Hefner hosting.
“Hefner promises beautiful models decorating a plush apartment setting and guests discussing jazz, sports cars, clothing styles, literature and other topics.”
— Chicago Tribune, Oct. 18, 1959
First Playboy Jazz Festival
The Chicago Stadium hosted a three-day, five-show jazz festival organized by Playboy and benefiting the Chicago Urban League, Aug. 7-9, 1959.
The first night’s performers, according to an Aug. 8, 1959, Chicago Tribune review, included Count Basie’s band, Miles Davis and Dave Brubeck. Brubeck was originally scheduled to perform the next night, but “because Aug. 8 is (classical composer Wolfgang Amadeus) Mozart’s birthday … he likes to spend the day with his kids.”
The next Playboy Jazz Festival wouldn’t take place until 1979 — in Los Angeles. Hollywood Bowl hosts the annual Playboy Jazz Festival , produced in coordination with the Los Angeles Philharmonic.
The Chicago Stadium was demolished in February 1995. The site is currently a parking lot across from the United Center.
“A reporter’s survey of the far reaches of the main floor, the mezzanine, and the top gallery, indicated that the sound, from the stage at the west end of the building, was coming in fine at all levels, and that the hot dogs weren’t bad either.”
— Chicago Tribune, Aug. 8, 1959
Palmolive (Playboy) Building
Known as the Palmolive Building, Hefner bought its leasehold in 1965. Playboy’s offices were completed in 1967, taking up 133,000 square feet on floors 4 through 12.
In an effort to save money, its operations would move to Lake Shore Place, 680 N. Lake Shore Drive, in 1988.
“One of the most important symbolic connections with the city was the beacon on the top of the 919 N. Michigan Ave. building. When we were kids, we could see that beacon sweeping across the sky at night. For me, it was like the wail of a railroad train passing by, part of that mystical yearning of youth and adolescence. I think that’s the reason that building eventually became the Playboy Building.”
— Hefner (Chicago Tribune, Feb. 20, 1994)
Playboy Towers Hotel
Built in 1927 and originally called the Knickerbocker Hotel, it became Playboy Towers in the early 1970s. According to “Mr. Playboy: Hugh Hefner and the American Dream” by Steven Watts, the Playboy name was removed from the hotel in 1976 when the company experienced money troubles.
Today, the 306-room hotel is known as the Millennium Knickerbocker Hotel Chicago.
“… one (United Auto Workers union) negotiator (staying at Playboy Towers during lengthy negotiations) piously deplores the absence of a Gideon Bible in his hotel room. The only thing available for spiritual inspiration, he reports, is a month-old issue of Playboy with the centerfold torn out!”
— Chicago Tribune, Jan. 20, 1971
Playboy Theater
Operating from 1913 to 1983, this theater had an ever-changing name. Starting in 1964 it was known as the Playboy Theater and ran a mix of offbeat movies.
After the theater was sold in 1976 and renamed Chelex Theater, Tribune movie critic Gene Siskel noted, “Management of the Playboy was a hapahazard affair over the years, even though Playboy chief Hugh Hefner is an avid film freak.”
Now, a 24-hour Walgreens stands at the site.
“We could have run ‘American Graffiti’ (a monster hit) exclusively three years ago, but we had to play Playboy’s own picture, ‘The Naked Ape,’ (a financial bust).”
— Ron Lichterman, theater manager (Chicago Tribune, Oct. 10, 1976)
Playboy Empire Club
The Chicago Playboy club moved over the years, ending up on the second floor of this high-rise apartment building. The last incarnation of the club included “Rabbits,” male versions of the Bunnies hired in an effort to attract women and couples. The club closed for good in 1986.
“Baby boomers found that, by the time they were old enough to attend Playboy clubs, they no longer wanted to. Hefner simply lost touch with his own revolution. To keep the clubs going, he would have had to change their name and drop the Bunnies, destroying his dream to save it.”
— Editorial by Clarence Page (Chicago Tribune, July 2, 1986)
Last Chicago office
In 1988, under the guidance of Hefner’s daughter, company president and chief operating officer Christie Hefner, Playboy moved its offices to Lake Shore Drive. It occupied 100,000 square feet of top two floors of Lake Shore Place.
Playboy consolidated its offices and moved operations to Los Angeles in 2012.
“In a funny kind of psychological way, moving during the 35th year (of operation) is a way of saying very definitely, ‘It’s a new look, a new culture, a company rooted more in the 1990s than in the 1960s or 1970s.”
— Christie Hefner (Chicago Tribune, April 10, 1988)
Site considered for new club
In 2011, plans were in the works to build a modern take on the classic 1960s nightclub under the Playboy name.
One of the sites considered was this mansion, which then housed Il Mulino restaurant. The project never came to fruition. The site has been transformed, however, into a cigar store and club.
“We think the Chicago market is going to react very favorably to what we’re going to offer.”
— Tom Morgan, backer of new Playboy Club, (Chicago Tribune, Aug. 29, 2011)
