History in Woodlawn

6052 South Harper Avenue

Hugh Hefner's Apartment

Playboy founder Hugh Hefner produced the first issue of Playboy Magazine in 1953 at the kitchen table of the apartment he shared with his wife, Millie, at 6052 South Harper Avenue.  Hefner's childhood home was located at 1922 North New England Avenue.  

History in Woodlawn

6220 South Stony Island Avenue

Hyde Park Career Academy

Hyde Park Career Academy at 6220 South Stony Island Avenue was founded in 1863 and operated from a series of locations until 1914, where it remains today. Its lengthy list of notable alumni includes famed aviator Amelia Earhart, Nobel Prize-winning economist Paul Samuelson, Pulitzer Prize-winning poet Gwendolyn Brooks, and musicians Mel Torme, Steve Allen, Herbie Hancock, and Minnie Riperton.  

6410 south dante avenue

Mount Carmel High School

Mount Carmel High School is an all-boys Catholic high school that was founded in 1900 at 6410 South Dante Avenue.  Its notable alumni include a long list of professional athletes, such as Donovan McNabb, Denny McLain, Chris Chelios, Simeon Rice, and Antoine Walker.  In addition, Craig Robinson, brother of First Lady Michelle Obama, graduated from Mount Carmel in 1979. 

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History in Woodlawn
Clubs and theaters

6400 South Cottage Grove Avenue


It started out as “Cadillac Bob’s Birdland,” but legal threats from the owners of New York’s famed “Birdland” forced a name change to “Budland.”  Located in the basement of the Pershing Hotel at 6400 South Cottage Grove Avenue (some sources say 6412 S. Cottage Grove), Budland was one of the most popular nightclubs in the city for 15 to 20 years. 

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868 East 63rd Street

Crown Propeller Lounge

By the early 1950s, the area along 63rd Street, straddling Cottage Grove, was the center of entertainment for the African-American community.  There were several jazz, rhythm and blues, doo-wop, and amateur night clubs, the most popular and prestigious of which was the Crown Propeller Lounge, at 868 East 63rd Street, underneath the el tracks.  The area was notoriously rich with drug dealers, drinkers, smokers, hookers, and people just looking for action. 

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6325 South Cottage Grove

McKie's Dsc Jockey Lounge

In 1956, a local disc jockey named McKie Fitzhugh took over the Strand Lounge on the first floor of the Strand Hotel at  6325 South Cottage Grove and turned it into a hip jazz outlet called McKie’s Disc Jockey Lounge.  The club had a notoriously small bandstand, but was not at all wanting for superstars.  Over the next decade, the D.J.

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6325 South Cottage Grove Avenue

Tivoli Theater

The Tivoli Theater was an impeccably designed, luxurious movie house reminiscent of the Palace of Versailles – a grandiose architectural wonder featuring a chiseled marble interior, crystal lighting throughout, and, for the convenience of guests, air-conditioning.  It was the first of “big three” movie palaces opened by Balaban & Katz and cost more than two million dollars to build and furnish. 

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6201 South Cottage Grove Avenue

Trianon Ballroom

The Trianon Ballroom was opened at 6201 South Cottage Grove Avenue  in 1922 by Andrew Karzas, who invested a million dollars attempting to capitalize on the various new dance crazes that were sweeping the country.  The building was lavishly, colorfully, and impeccably furnished in the style of Louis XVI, with a vast ballroom that accommodated more than 3,000 people, a mezzanine level, a beautiful stage, a grandiose front lobby, and a luxuriously appointed lounge.

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