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Playboy Legacy Boxed Set /Gold Edition - Authorized by: Hugh Hefner - #20 of 75
By Playboy Enterprises
Located in New York, NY
Legacy Collection, published in 2007 by Playboy Enterprises International, Chicago. • Certificate of
Category

21st Century and Contemporary Hard-Edge Mixed Media

Materials

Silver Gelatin, Oak

Playboy Legacy Boxed Set /Gold Edition - Authorized by: Hugh Hefner - #20 of 75
By Playboy Enterprises
Located in New York, NY
Legacy Collection, published in 2007 by Playboy Enterprises International, Chicago. • Certificate of
Category

21st Century and Contemporary Hard-Edge Mixed Media

Materials

Oak, Archival Paper, Silver Gelatin

Man's Work, 1960: Hugh Hefner and Bunnies at the Playboy Key Club, Chicago
By Slim Aarons
Located in New York, NY
Man's Work, 1960: Hugh Hefner and Bunnies at the Playboy Key Club, Chicago Staley-Wise Gallery
Category

1960s Color Photography

Materials

C Print

Party At The Playboy Mansion Slim Aarons Estate Stamped Print
By Slim Aarons
Located in London, GB
American publisher Hugh Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago
Category

1960s Modern Color Photography

Materials

Archival Pigment

Slim Aarons Official Estate Print - Party At The Playboy Mansion
By Slim Aarons
Located in London, GB
enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim Aarons
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion X
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Hugh Hefner at The Playboy mansion, Black and White Photography 1960s
By Burt Glinn
Located in New york, NY
Hugh Hefner, 1966 by Burt Glinn is a 16" x 20" portrait in Chicago, IL of the founder of playboy
Category

2010s Contemporary Portrait Photography

Materials

Silver Gelatin, Photographic Film, Photographic Paper

Playboy: 35th Anniversary Poster /// Pop Art Andy Warhol Screenprint Bunny Head
By Andy Warhol
Located in Saint Augustine, FL
Artist: (after) Andy Warhol (American, 1928-1987) Title: "Playboy: 35th Anniversary" *Signed by
Category

1980s Pop Art Portrait Prints

Materials

Screen

'Party At The Playboy Mansion' 1961 Slim Aarons Limited Estate Edition
By Slim Aarons
Located in London, GB
publisher Hugh Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion IX
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion IV
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion V
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion XI
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion VII
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion VI
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion III
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion VIII
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

Slim Aarons Official Estate Print - Party At The Playboy Mansion II
By Slim Aarons
Located in London, GB
Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 1961. (Photo by Slim
Category

1960s Modern Color Photography

Materials

C Print, Color

White Bunny Drawing by Oleg Cassini for Playboy October 1979, Signed
By Oleg Cassini
Located in Brooklyn, NY
White Bunny Drawing by Oleg Cassini for Playboy October 1979, Signed. Illustration of a woman
Category

Mid-20th Century Italian Drawings

Materials

Paper

Ted Williams 'Dr. Martin Luther King, Chicago'
By Ted Williams
Located in New York, NY
Rally for Civil Rights’ at Soldier Field in Chicago, IL, US, June 21, 1964. The same day of the murders
Category

1960s Modern Portrait Photography

Materials

Silver Gelatin

Playboys (2 American male refugees from the Gatsby era preen on Mexican beach)
By Caroline Durieux
Located in New Orleans, LA
In these beady-eyed playboys, Durieux pokes some fun at the pride and pretensions of the Great
Category

1930s American Modern Portrait Prints

Materials

Lithograph

Observant Father, 1949, Chicago, Vintage Silver Gelatin Print
By Art Shay
Located in Chicago, IL
capture moments like this one - a priest on a Chicago street "observing" one of his parishioners. Art saw
Category

1940s Contemporary Black and White Photography

Materials

Silver Gelatin

Beat Artist "Witness" Lithograph Etching Lakeside Studio Chicago
Located in Surfside, FL
Will Petersen, a painter, master printer and a poet, was born in Chicago. (Amer. 1928-1994) created
Category

20th Century Abstract Expressionist Abstract Prints

Materials

Etching, Lithograph

Liz Taylor Smelling Smell-O-Vision, Chicago, 1960
By Art Shay
Located in Chicago, IL
murdered. Photographed here by Art Shay with her then husband, Eddie Fisher, at the premier in Chicago
Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Beat Artist "Double Witness" Lithograph Etching Lakeside Studio Chicago
Located in Surfside, FL
Will Petersen, a painter, master printer and a poet, was born in Chicago. (Amer. 1928-1994) created
Category

20th Century Abstract Expressionist Abstract Prints

Materials

Etching, Lithograph

Young Pool Shark, Chicago 1949, Black & White Photograph, Framed, Signed
By Art Shay
Located in Chicago, IL
- before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice. Art
Category

1940s Contemporary Black and White Photography

Materials

Silver Gelatin

Two Leopards Spotted, Chicago 1974, Brookfield Zoo, Signed and Framed.
By Art Shay
Located in Chicago, IL
a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner
Category

1970s Contemporary Black and White Photography

Materials

Silver Gelatin

Seurat's A La Grande Jatte with Marcel Marceau, Chicago, 1958
By Art Shay
Located in Chicago, IL
"Sunday Afternoon" at the Art Institute of Chicago. Art Shay A La Grande Jatte, 1958 silver gelatin print
Category

1970s Contemporary Black and White Photography

Materials

Silver Gelatin

Girls Girls Girls, State St. Strip Joint Near Death, Chicago, 1966
By Art Shay
Located in Chicago, IL
coordinated bombings of Chicago porn houses - the Rialto Theatre, Follies Theatre, Newberry Theatre, and Bijou
Category

21st Century and Contemporary Contemporary Black and White Photography

Materials

Archival Pigment

Vintage Chicago Architect Stanley Tigerman Cloisonne Enamel Art Necklace Acme
Located in Surfside, FL
and Ken Price all designed for Acme Studio as well as famed Playboy Magazine artist Patrick Nagel.
Category

1980s Pop Art More Art

Materials

Metal, Enamel

Hugh Hefner in His Bedroom Office, Chicago 1961, Black and White Photography
By Art Shay
Located in Chicago, IL
"Nelson Algren's Chicago: Photographs by Art Shay", page 34. Hugh Hefner liked Algren and vice
Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

The Nixons on LaSalle Street, Chicago, 1968, Color Photograph, Signed on Back
By Art Shay
Located in Chicago, IL
campaign trail during the 1968 presidential election. The photograph was taken on Chicago's famed LaSalle
Category

1960s Contemporary Color Photography

Materials

Archival Pigment

Maxwell Street Dog, Black & White Street Photography, Chicago, 1953 by Art Shay
By Art Shay
Located in Chicago, IL
Dog". A Chicago tradition running for about 100 years, the Maxwell Street Market was (and still is) a
Category

21st Century and Contemporary Contemporary Black and White Photography

Materials

Silver Gelatin

Mafia Boss Tony "Big Tuna" Accardo in Front of Big Lion, Chicago 1959
By Art Shay
Located in Chicago, IL
- before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice. Art
Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Blues Great Howlin' Wolf, Chicago 1966, Framed Black and White Photo by Art Shay
By Art Shay
Located in Chicago, IL
a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner
Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Man’s Work Slim Aarons Estate Stamped Print
By Slim Aarons
Located in London, GB
surrounded by ‘bunny girls’, publisher Hugh M Hefner at the Playboy Key Club in Chicago. He founded adult
Category

1960s Modern Color Photography

Materials

Archival Pigment

Hugh Hefner Slim Aarons Estate Stamped Print
By Slim Aarons
Located in London, GB
Hefner, founder of ‘Playboy’ magazine, surrounded by erotica at the Playboy Club in Chicago, 1961
Category

1960s Modern Color Photography

Materials

Archival Pigment

Hugh Hefner Slim Aarons Estate Stamped Print
By Slim Aarons
Located in London, GB
Hefner, founder of ‘Playboy’ magazine, surrounded by erotica at the Playboy Club in Chicago, 1961
Category

1960s Modern Color Photography

Materials

Archival Pigment

Hang Twenty with Spuds MacKenzie, Bud Light
Located in Sag Harbor, NY
. Anheuser-Busch’s Bud Light and Omnicom Group’s DDB Needham Chicago created a phenomenon among marketing
Category

21st Century and Contemporary Posters

Materials

Paper

Eyeball Freak, Circus Side Show Curiosity, Silver Gelatin Print, Framed, 1952
By Art Shay
Located in Chicago, IL
- before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice. Art
Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

LeRoy Neiman 'Femling - Happy New Year 1992' Original ink & watercolor
By LeRoy Neiman
Located in Pembroke Pines, FL
the Carson Pirie Scott department store in Chicago. While working there he would meet Hugh Hefner, who
Category

1990s Contemporary Figurative Drawings and Watercolors

Materials

Watercolor, Ink

LeRoy Neiman 'Femling with A HOT Iron' Original ink & watercolor
By LeRoy Neiman
Located in Pembroke Pines, FL
the Carson Pirie Scott department store in Chicago. While working there he would meet Hugh Hefner, who
Category

1960s Contemporary Figurative Drawings and Watercolors

Materials

Ink, Watercolor

U.S. Open at Oakmont
By LeRoy Neiman
Located in Missouri, MO
of Chicago, the University of Chicago, and the University of Illinois. His mediums are oil, enamel
Category

20th Century American Modern Landscape Prints

Materials

Color, Lithograph

The 18th at Pebble Beach
By LeRoy Neiman
Located in Missouri, MO
Institute of Chicago, the University of Chicago, and the University of Illinois. His mediums are oil
Category

20th Century American Modern Landscape Prints

Materials

Color, Lithograph

Cove at Vintage
By LeRoy Neiman
Located in Missouri, MO
of Chicago, the University of Chicago, and the University of Illinois. His mediums are oil, enamel
Category

20th Century American Modern Landscape Prints

Materials

Color, Lithograph

Marlon Brando, Libertyville, Illinois, 1950 - Silver Gelatin Print
By Art Shay
Located in Chicago, IL
Libertyville, Illinois, just north of Chicago. Looking straight into Art's lens, Brando is innocent of the
Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Tracks to War, New Jersey, 1943, Black and White Photograph, Signed, Framed
By Art Shay
Located in Chicago, IL
- before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice. Art
Category

Mid-20th Century Contemporary Black and White Photography

Materials

Silver Gelatin

A Farm Grandma Waiting for Kids, 1951
By Art Shay
Located in Chicago, IL
- before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice. Art
Category

1950s Contemporary Black and White Photography

Materials

Archival Pigment

JFK in Profile, 1960 - Color Photograph Matted and Framed
By Art Shay
Located in Chicago, IL
photojournalists I know. I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine
Category

2010s Contemporary Color Photography

Materials

Archival Pigment

Ted Williams 'Duke Ellington'
By Ted Williams
Located in New York, NY
University of Chicago, 1960. Ted Williams (1925-2009) first heard jazz on the radio as a youngster in the
Category

1960s Modern Portrait Photography

Materials

Silver Gelatin

Ted Williams 'Billie Holliday'
By Ted Williams
Located in New York, NY
stamped and numbered edition 25 with certificate of authenticity Billie Holiday on-stage in Chicago
Category

1960s Modern Portrait Photography

Materials

Silver Gelatin

Ted Williams 'Count Basie'
By Ted Williams
Located in New York, NY
and numbered edition 25 with certificate of authenticity Count Basie at the Trianon Ballroom, Chicago
Category

1960s Modern Portrait Photography

Materials

Silver Gelatin

Ted Williams 'Louis Armstrong'
By Ted Williams
Located in New York, NY
of Chicago Theater in the Round, 1962 Ted Williams (1925-2009) first heard jazz on the radio as a
Category

1960s Modern Portrait Photography

Materials

Silver Gelatin

Gale Sayers #40, 1966 - Color Photograph by Art Shay for Sports Illustrated
By Art Shay
Located in Chicago, IL
photojournalists I know. I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine
Category

1960s Contemporary Color Photography

Materials

Archival Pigment

'Hugh Hefner' 1961 Slim Aarons Limited Estate Edition
By Slim Aarons
Located in London, GB
, founder of 'Playboy' magazine, surrounded by erotica at the Playboy Club in Chicago, 1961. Produced from
Category

1960s Modern Color Photography

Materials

Color

Car Reflection, 1958, Black and White Photograph Appeared in LIFE Magazine
By Art Shay
Located in Chicago, IL
photojournalists I know. I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine
Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Titter, Scantily Clad Woman Viewing Titter Magazine, 1950 Vintage Photograph
By Art Shay
Located in Chicago, IL
- before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice. Art
Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

"Frank Sinatra as Tony Rome"
By LeRoy Neiman
Located in Lambertville, NJ
Institute of Chicago and later, teaching figure drawing and fashion illustration there. While working at the
Category

Mid-20th Century Figurative Paintings

Materials

Paper, Oil

Blues Guitarist, Buddy Guy, 1966, Playing Guitar, Framed Photograph by Art Shay
By Art Shay
Located in Chicago, IL
the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they
Category

1960s Contemporary Black and White Photography

Materials

Archival Pigment

The Man With the Golden Arm, 1949, Nelson Algren as the Dealer, Silver Gelatin
By Art Shay
Located in Chicago, IL
photojournalists I know. I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine
Category

1940s Contemporary Black and White Photography

Materials

Silver Leaf

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Playboy Chicago For Sale on 1stDibs

Find the exact playboy chicago you’re shopping for in the variety available on 1stDibs. You can easily find an example made in the modern style, while we also have 81 modern versions to choose from as well. If you’re looking for a playboy chicago from a specific time period, our collection is diverse and broad-ranging, and you’ll find at least one that dates back to the 19th Century while another version may have been produced as recently as the 21st Century. Adding a playboy chicago to a room that is mostly decorated in warm neutral tones can yield a welcome change — find a piece on 1stDibs that incorporates elements of black, gray, beige, blue and more. There have been many interesting playboy chicago examples over the years, but those made by Art Shay, Leroy Neiman, Robert Branham, Slim Aarons and Ted Williams are often thought to be among the most thought-provoking. Frequently made by artists working in silver gelatin print, paint and archival pigment print, these artworks are unique and have attracted attention over the years.

How Much is a Playboy Chicago?

A playboy chicago can differ in price owing to various characteristics — the average selling price for items in our inventory is $3,000, while the lowest priced sells for $295 and the highest can go for as much as $375,000.