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In August 1999, Jim McBride launched what is now MrSkin.com, a website devoted to cataloging on-screen nudity by female celebrities, in a 39th-floor apartment at Ontario Place (10 E. Ontario St.). The business later relocated to Bucktown.
In the Viagra Triangle (bounded by Chicago Avenue and State and Rush streets), rich older men prey on pretty young women—or is it the other way around?
On December 27, 1934, acting on orders from Mayor Ed Kelly, police closed the Star and Garter (815 West Madison St.), an old burlesque house famous for nude girlie shows and prostitution. That same day, they also shut down two women’s cross-dressing clubs: the Rosal (1251 N. Clark St.) and the 1230 (1230 N. Clybourn Ave.).
In a 1946 drawing class at the Art Institute of Chicago (111 S. Michigan Ave.), a 20-year-old Hugh Hefner first laid eyes on a fully nude woman.
In October 1913, under the direction of superintendent Ella Flagg Young, the Chicago Public Schools, headquartered at 7 South Dearborn Street, launched the country’s first sexual education classes. Fearing that students were being corrupted, protesting parents and school board members shut down the program in June 1914.
At the Reliance Building (32 N. State St.) in the 1930s, Dr. Ben Reitman treated tramps, prostitutes, and other “undesirables” for syphilis.
In February 1915, some 1,500 people gathered at Orchestra Hall (220 S. Michigan Ave.) to hear Edith Lees Ellis, the openly lesbian wife of the British sexologist Havelock Ellis, deliver a speech entitled “Sexuality and Eugenics,” an early modern defense of homosexuality.
Triumph Gym(22 W. Van Buren St.) was the setting for beefcake photos shot for Mars magazine, a short-lived gay publication from 1963.
Kitty-corner from today’s Harold Washington Library (400 S. State St.) stood a late 19th-century “Panel House,” an unscrupulous brothel. When a john hung his clothes on a strategically located chair or peg in the hooker’s room, her confederate, hidden behind the wall, slid open a panel and stole the man’s wallet.
When Nicholas de Raylan, a Spanish-American War veteran and secretary to the Russian consul in Chicago, died in 1906, he left behind a surprise: “He” was actually a woman—which came as a shock to his two former wives. The consulate stood at the southwest corner of LaSalle and Adams streets.
In the early decades of the 20th century, Max Stein Publishing (508 S. State St.) printed Confessions of a French Stenographer and other supposedly racy literature.
Beginning in 1971, Weird Harold’s (541 S. Wabash Ave.) was home to an adult bookstore, a massage parlor, and nude models interested in more than just a photo session. After a series of police raids, the city shut down the store in 1975.
On February 25, 1968, at the Conrad Hilton hotel (720 S. Michigan Ave.), Cynthia Plaster Caster—born in Chicago in 1947 as Cynthia Albritton—made a plaster cast of Jimi Hendrix’s penis.
After sensationally appearing as a nearly naked equestrian Lady Godiva at the opening of the Century of Progress Exposition in 1933, Sally Rand went on to titillate fairgoers with her ostrich-feather fan dances.
Managed by Minna and Ada Simms from 1900 to 1911, the Everleigh Club (2131 S. Dearborn St.) was the city’s most sumptuous brothel.
The Sappho (2159 S. Dearborn St.), in the Levee vice district, staged lesbian entertainments for male customers.
Owned by the white slaver Ike Bloom, Freiberg’s Dance Hall (20 E. 22nd St.) offered liquor and sex, ending its 19-year run after it was shut down by reformers in 1914; reborn as the Midnight Frolics, it burned down in 1934.
On January 16, 1914, likely at the College of Medicine at the University of Illinois (situated then at Harrison and Wolcott streets), Dr. G. Frank Lydston, striving (unsuccessfully) for sexual revitalization, grafted onto himself a testicle removed from a dead young man.
From 1865 to 1890, Erring Women’s Refuge (3111 S. Indiana Ave.) helped prostitutes get out of the sex trade by providing them education, job training, and medical care.
The Cozy Cabin Club (3119 S. Cottage Grove Ave.), billed in the 1930s as “Chicago’s Oddest Nightery,” drew mixed-race audiences for performances by black female impersonators.
The trumpeter Ernestine “Tiny” Davis and her partner, the drummer Ruby Lucas, ran the 1950s lesbian bar Tiny and Ruby’s Gay Spot (2711 S. Wentworth Ave.); it was demolished to make way for the Dan Ryan Expressway.
Finnie’s Ball, an annual black drag ball that began in a basement bar near 38th Street and Michigan Avenue in 1935, continued into the 1960s at the Chicago Coliseum (1653 S. Wabash Ave.).
At the apartment (6052 S. Harper Ave.) he shared with his wife, Millie, Hugh Hefner produced the first issue of Playboy in 1953.
On the Midway Plaisance of the 1893 World’s Columbian Exposition, the dancer Little Egypt entranced men with her suggestive gyrations.
In 1965, Jimmy Fleming, an African American, bought The Jeffery Pub (7041 S. Jeffery Blvd.). Today it is the oldest gay bar in Chicago.
In the early 1950s, the John Baumgarth Calendar Co. (3001 W. North Ave., Melrose Park) printed a girlie calendar with a retouched photo of a naked Marilyn Monroe (the company had added a swimsuit to the picture); Hugh Hefner later bought the nude photo for the first issue of Playboy.