Hef’s Galewood Homestead

With Playboy magazine on the ropes, this section from my book Hidden Chicago Landmarks seems timely.

Many Chicago tours will take time to point out the massively-elegant brick-and-limestone building at 1340 North State Street. Today it is divided into condos. In an earlier era it was the original Playboy Mansion. Hugh Hefner lived here from 1959 through 1975, before decamping to Los Angeles. This is where he perfected the persona and lifestyle that made him famous—or notorious, depending on your point of view.

The South Side apartment building where Hefner created Playboy magazine is long gone. But his childhood home still stands on the city’s far West Side, at 1922 North New England Avenue.

Hugh Hefner was four years old when his family moved into the newly-built brick home in the Galewood section of Austin. His father Glenn was an accountant, his mother Grace a homemaker and part-time teacher. The year was 1930, and the Depression was just getting underway. Glenn had to work long hours to scrape by, leaving the raising of Hugh and his younger brother mostly to his wife.

The Galewood neighborhood was still sparsely settled during the 1930s. Hugh remembered growing up amid prairies and prairie animals, with gas street lamps and milk delivered from horse-drawn wagons. During the week he went to the Sayre Elementary School, a couple of blocks from his home. Sundays meant services at the local Methodist church.

Hugh was an underachiever at Sayre. Teachers observed that he was intelligent, yet would work hard only at those things which interested him. He seemed to be living in a world of his own. He liked to write stories and was especially skilled as a cartoonist.

At Steinmetz High School, Hugh reinvented himself. Outside the circle of his closest friends, he’d always been shy. Now he upgraded his wardrobe, adopted a confident demeanor, and literally forced himself to become more outgoing. He also began referring to himself in the third person as “Hef.” “I became the imaginary adolescent, the teenager I wanted to be,” he later said.

It paid off. By sophomore year Hefner had become the leader of the school’s self-styled sophisticates. He wrote copy and drew cartoons for the school newspaper, appeared in plays, and even filmed his own fifteen-minute horror film. As a senior he was elected president of the Student Council.

Hefner graduated from Steinmetz in January 1944. World War II was on, and shortly afterward he enlisted in the army. Trained as an infantry rifleman, he wound up serving stateside as a clerk. He was discharged as a corporal in 1946.

Hefner used the G.I. Bill to attend the University of Illinois at Urbana. His girlfriend Millie Williams was already a student there. He graduated from the accelerated program with a degree in Psychology in 1949, married Millie, and returned to Chicago.

The newlyweds moved in with Glenn and Grace on New England Avenue. They made do with a single large bedroom. Postwar housing was in short supply, and they didn’t have much money, anyway. While Millie worked at the nearby Mars candy factory, Hugh drifted through a series of jobs. He enrolled in a graduate program in Sociology at Northwestern, but dropped out after one semester.

In the spring of 1952 Millie Hefner became pregnant. The couple finally moved out of the house in Galewood, renting an apartment at 6052 South Harper Avenue. Hugh saw his cosmopolitan new neighborhood near the University of Chicago as “a sort of Greenwich Village.” It was here that he put together his magazine in the fall of 1953.

Hugh’s parents continued to live on New England Avenue while their elder son became famous. Glenn Hefner died in 1976. Grace sold the house and moved to Arizona nine years later. She died in 1997, at the age of 102.

Hugh Hefner made a number of sentimental journeys back to Galewood in the years following his move to Los Angeles. The 1992 documentary Hugh Hefner: Once Upon a Time includes scenes from one such trip. After his death in 2017 there was some discussion about turning his boyhood home into a museum. Nothing has been done as yet, and the house remains a private residence.

For this story and 59 more, buy a copy of my book Hidden Chicago Landmarks. Available in print or on kindle.