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.  Robinson was a two-time Ivy League Player Of The Year at Princeton University and is currently the head coach of the men’s basketball team at Oregon State.  Cook County Sheriff Tom Dart also attended the school.

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.  It started out as a premier jazz club in one of the most fertile jazz districts in the city and featured such legends as Charlie Parker, Miles Davis, Lester Young, Dizzy Gillespie, Billie Holiday, Dinah Washington, and Sun Ra in the mid-1950s.  By the late 1950s, it began catering to doo-wop music, and in the early 1960s it became steeped in soul and rhythm-and-blues.  Budland reportedly featured the “baddest” dancers in town during its soul years.  It was generally accepted that you dared not enter Budland unless you could flaunt serious dance moves.

In 1964, Budland’s owner, Warren Taylor, died of a heart attack while at the club.

The Pershing Hotel, which has since been demolished, featured a sprawling ballroom that accommodated 2,000 partygoers, as well as a lounge that was highly popular in the 1940s, where it operated under such names as “Club Bagdad,” the “Beige Room,” and the “El Grotto Café.”  Big band legends like Tiny Bradshaw frequently headlined there.

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.  Prior to 1951, there was an unofficial “color line” along 63rd Street, with African-Americans strictly on the west side of Cottage Grove.  After that line was broken, nightclubs catering primarily to African-American clientele, such as the Crown Propeller Lounge, began opening on the east side of Cottage Grove.  During the club’s first year in business, LaVern Baker played an extended engagement here as “Little Miss Sharecropper.”

Today, the cultural richness of this area has all but vanished.  There are long strings of vacant lots along 63rd Street, leaving no trace of the vibrant club scene that flourished here in the 1950s.

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. Lounge (as it was sometimes called) featured Dizzy Gillespie, Ben Webster, Max Roach, Roy Eldridge, Gene Ammons, Sonny Stitt, Ahmad Jamal, and John Coltrane (who appeared there in 1964 with McCoy Tyner, Jimmy Garrison, and Elvin Jones).  The club also paid tribute to local disc jockeys and frequently blared popular rhythm-and-blues hits of the day.

When McKie Fitzhugh died of a heart attack in 1970 at the age of 55, Jet Magazine called it the end of an era.  His Disc Jockey Lounge was perhaps the last hip jazz club in the city.  As for the end of an era, jazz had been living on borrowed time since the day the Beatles landed at Kennedy Airport six years earlier.

Meanwhile, the Strand Hotel, from which McKie’s Disc Jockey Lounge operated, remains on the site today.

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.  Located at 6325 South Cottage Grove Avenue  between the Strand Hotel and the Cinderella Ball Room, it attracted 20,000 locals for opening night on February 16, 1921, although most of those who patiently queued along Cottage Grove Avenue were unable to gain admission.  The theater seated 4,500 patrons and accommodated an additional 3,000 in the lobby, and daily attendance of over 7,000 was reportedly commonplace throughout the 1920s.  Not just a neighborhood attraction, the theater was designed to, and did, draw moviegoers from all over the city.  Patrons were expected to behave respectably and dress appropriately.  Juvenile or sexually forward behavior was not tolerated, and male ushers were uniformed and trained like soldiers to enforce decorum with authority.

In January of 1959, the Tivoli became a venue for live jazz music.  Pearl Bailey played there first, followed by Fats Domino, Count Basie, Louis Jordan, Ahmad Jamal, Cannonball Adderley, Carmen McRae, Duke Ellington, and Art Blakey.  The theater closed in September of 1963.  It was demolished shortly thereafter.  Today the site is occupied by a Dollar Store and its parking lot.

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.

The Trianon was notorious for rigidly enforcing decency and prevailing social etiquette.  Employees intervened to prevent petting, spooning, and other public displays of affection, and women were not permitted to smoke.  The club also observed a whites-only admission policy until the mid-1950s.

From an entertainment perspective, the Trianon Ballroom was strictly milk-toast.  It was not the place to catch the latest, hippest, most avant-garde jazz of the day.   Featured instead were orchestras led by folks like Paul Whiteman, Dell Lampe, and Isham Jones, whose softer approach to big band music was more palatable to middle-class whites than the “jungle music” being churned out by such luminaries as Duke Ellington, Count Basie, and Earl “Fatha” Hines.

In 1954, the ballroom was “reopened” in an attempt to recapture some of its former glory.  At this point, “everybody” was now welcome, which meant that African-Americans would no longer be refused admission.  Horace Henderson & His Orchestra played a few weeks in July of 1954 and recorded a live album from the ballroom, but the Trianon’s days were over, and it closed shortly thereafter.  The building was demolished in 1967.

(Incidentally, there were Trianon Ballrooms in other cities across the country, but all were independently owned and unaffiliated.)