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Hugh Hefner - Photograph by Emmett Graham - 2023

Hugh Hefner - Photograph by Emmett Graham - 2023

By Emmett Graham

Located in Roma, IT

This was created due to the passing of Hugh Hefner who who is known through out the world wide as the man who created "Play Boy" magazine.

Category

2010s Contemporary Photography

Materials

Photographic Paper

Hugh Hefner Slim Aarons Estate Stamped Print
Hugh Hefner Slim Aarons Estate Stamped Print

Hugh Hefner Slim Aarons Estate Stamped Print

By Slim Aarons

Located in London, GB

Hugh Hefner American publisher Hugh Hefner, founder of ‘Playboy’ magazine, surrounded by erotica at the Playboy Club in Chicago, 1961. 24 x 20" - paper size Estate Stamped Coll...

Category

1960s Modern Color Photography

Materials

Archival Pigment, Color

Hugh Hefner Slim Aarons Estate Stamped Print
Hugh Hefner Slim Aarons Estate Stamped Print

Hugh Hefner Slim Aarons Estate Stamped Print

By Slim Aarons

Located in London, GB

Hugh Hefner American publisher Hugh Hefner, founder of ‘Playboy’ magazine, surrounded by erotica at the Playboy Club in Chicago, 1961. 24 x 20" - paper size Estate Stamped Coll...

Category

1960s Modern Color Photography

Materials

Archival Pigment, Color

Marilyn vs Hugh Hefner

Alex Guofeng CaoMarilyn vs Hugh Hefner, 2014

Price Upon Request

H 60 in W 40 in D 2 in

Marilyn vs Hugh Hefner

By Alex Guofeng Cao

Located in New York, NY

In a captivating new collection, Alex Guofeng Cao dazzles audiences with his unique twist on instantly recognizable images. Inspired by history and pop culture, Cao manipulates one i...

Category

2010s Contemporary Figurative Prints

Materials

Plexiglass, Archival Ink, Mixed Media, Acrylic, Archival Paper, Archival...

Hugh Hefner With Playmates, 1979 by Julian Wasser

Hugh Hefner With Playmates, 1979 by Julian Wasser

By Julian Wasser

Located in Chicago, IL

Hugh Hefner with Playmates, 1979 Hefner hosted an annual Playmate of the Year reunion.

Category

20th Century Contemporary Black and White Photography

Materials

Silver Gelatin

Hugh Hefner Philosophy, Vintage Gelatin Silver Photograph, 1966, 12x8
Hugh Hefner Philosophy, Vintage Gelatin Silver Photograph, 1966, 12x8

Hugh Hefner Philosophy, Vintage Gelatin Silver Photograph, 1966, 12x8

By Burt Glinn

Located in New york, NY

By photographer Burt Glinn a black-and-white 12" x 8" vintage gelatin silver photograph of Editor-in-chief Hugh Hefner who founded, edited, and wrote for Playboy.

Category

1960s Contemporary Portrait Photography

Materials

Silver Gelatin, Photographic Film, Photographic Paper

Hugh Hefner Portrait, Gelatin Silver Photograph, 1966, Signed, 16x20
Hugh Hefner Portrait, Gelatin Silver Photograph, 1966, Signed, 16x20

Hugh Hefner Portrait, Gelatin Silver Photograph, 1966, Signed, 16x20

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 magazine.

Category

2010s Contemporary Portrait Photography

Materials

Silver Gelatin, Photographic Film, Photographic Paper

Man's Work, 1960: Hugh Hefner and Bunnies at the Playboy Key Club, Chicago

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 offers photographic prints from the Slim Aarons Archive, owned and housed by Getty Ima...

Category

1960s Color Photography

Materials

C Print

Playboy Hugh Hefner, Vintage Black and White Photograph, 1966, 12x8 Inches
Playboy Hugh Hefner, Vintage Black and White Photograph, 1966, 12x8 Inches

Playboy Hugh Hefner, Vintage Black and White Photograph, 1966, 12x8 Inches

By Burt Glinn

Located in New york, NY

A black-and-white 12" x 8" vintage photograph of Editor-in-chief Hugh Hefner checking proofs for Playboy magazine, 1966 by Burt Glinn.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin, Photographic Film, Photographic Paper

Hugh Hefner Philosophy, Signed, Black and White Gelatin Silver Print, 1960s
Hugh Hefner Philosophy, Signed, Black and White Gelatin Silver Print, 1960s

Hugh Hefner Philosophy, Signed, Black and White Gelatin Silver Print, 1960s

By Burt Glinn

Located in New york, NY

By American photographer Burt Glinn a black-and-white 14" x 11" photograph on fiber paper (gelatin silver print) of Editor-in-chief Hugh Hefner who wrote for the magazine he founded,...

Category

1960s Contemporary Portrait Photography

Materials

Photographic Film, Photographic Paper, Silver Gelatin

Hugh Hefner Hits the Roller Rink With Playmates, 1974 by Julian Wasser

Hugh Hefner Hits the Roller Rink With Playmates, 1974 by Julian Wasser

By Julian Wasser

Located in Chicago, IL

Hugh Hefner on roller-skates at the Playboy Mansion, circa 1974 Hefner liked to roller-skate with his Playmates during Sunday afternoon parties at the Playboy Mansion.

Category

20th Century Contemporary Black and White Photography

Materials

Silver Gelatin

Beginning of the Work Day
Beginning of the Work Day

CeravoloBeginning of the Work Day, 2025

$8,500

H 32 in W 34 in D 2 in

Beginning of the Work Day

By Ceravolo

Located in Southampton, NY

Widely acclaimed as the "Rock and Roll Painter" and "Painter of the Stars of Rock" by the media, his work has found a coveted place in the collections of music royalty, including Elt...

Category

2010s Pop Art Mixed Media

Materials

Canvas, Mixed Media, Oil, Spray Paint, Acrylic

Party At The Playboy Mansion Slim Aarons Estate Stamped Print

Party At The Playboy Mansion Slim Aarons Estate Stamped Print

By Slim Aarons

Located in London, GB

Party At The Playboy Mansion 1961 by Slim Aarons Slim Aarons Limited Estate Edition Guests of American publisher Hugh Hefner enjoying themselves at a party being held at the Playb...

Category

1960s Modern Color Photography

Materials

Archival Pigment

"Ben-day Sophia 1" Mixed media, Acrylic, spray paint, pigmented ink 36x28 canvas
"Ben-day Sophia 1" Mixed media, Acrylic, spray paint, pigmented ink 36x28 canvas

"Ben-day Sophia 1" Mixed media, Acrylic, spray paint, pigmented ink 36x28 canvas

By Ceravolo

Located in Southampton, NY

His work is collected worldwide and is in many important collections including, Sir Elton John, Rod Stewart, Hugh Hefner and Prince Jefri of Brunei to name only a few.

Category

2010s Pop Art Portrait Paintings

Materials

Canvas, Oil, Spray Paint, Acrylic, Mixed Media

Bettie Page in Leopard -  Oversize Limited Print

Bettie Page in Leopard - Oversize Limited Print

By Irving Klaw

Located in London, GB

After her death, Playboy founder Hugh Hefner called her "a remarkable lady, an iconic figure in pop culture who influenced sexuality, taste in fashion, someone who had a tremendous i...

Category

2010s Modern Color Photography

Materials

Archival Pigment

Hot Girls. Hot Cars. Arnolt Bristol - Blue Sports Car Mid-Century - Playboy
Hot Girls. Hot Cars. Arnolt Bristol - Blue Sports Car Mid-Century - Playboy

Hot Girls. Hot Cars. Arnolt Bristol - Blue Sports Car Mid-Century - Playboy

By Ben Denison

Located in Miami, FL

The work also appears on page 13 of Playboy 50 Years: The Cartoons by Hugh Hefner (Chronicle Books, 2004). Framed under glass in a new high-end metal frame.

Category

1950s American Modern Figurative Paintings

Materials

Gouache, Illustration Board

Woman at Wall
Woman at Wall

George TookerWoman at Wall, 1973

$30,000

H 14.25 in W 10.24 in D 2 in

Woman at Wall

By George Tooker

Located in Miami, FL

In the former collection of Art Paul, who with Hugh Hefner created Playboy. Peter B. Ornstein, Brooklyn, New York, November 1974; Arthur Paul, Chicago, Illinois, acquired from the ab...

Category

1970s Realist Drawings and Watercolor Paintings

Materials

Paper, Pencil

Couple Reading
Couple Reading

Barbara A. WoodCouple Reading, Circa 1980

$510

H 22.5 in W 18.85 in D 1 in

Couple Reading

By Barbara A. Wood

Located in San Francisco, CA

Bush, Georgia Governor Sonny Perdue, Elizabeth Taylor, Hugh Hefner, Jane Seymour, Jerry Lewis, Mickey Rooney, Dick Van Dyke, Dennis Weaver, Art Linkletter, Ron Howard, Gavin MacLeod,...

Category

Late 20th Century Modern Figurative Prints

Materials

Offset

At The Park
At The Park

Barbara A. WoodAt The Park, Circa 1980

$638

H 26.25 in W 20.25 in D 1 in

At The Park

By Barbara A. Wood

Located in San Francisco, CA

Bush, Georgia Governor Sonny Perdue, Elizabeth Taylor, Hugh Hefner, Jane Seymour, Jerry Lewis, Mickey Rooney, Dick Van Dyke, Dennis Weaver, Art Linkletter, Ron Howard, Gavin MacLeod,...

Category

Late 20th Century Modern Figurative Prints

Materials

Offset

Slim Aarons, 'Playboy Party' Midcentury Modern Photography
Slim Aarons, 'Playboy Party' Midcentury Modern Photography

Slim Aarons, 'Playboy Party' Midcentury Modern Photography

By Slim Aarons

Located in New York, NY

Guests of American publisher Hugh Hefner, December 1961. Slim Aarons Playboy Party 1961 (printed later) C print Estate stamped and numbered edition of 150 with Certificate of aut...

Category

1960s Modern Color Photography

Materials

C Print

Intermission
Intermission

Barbara A. WoodIntermission, 1995

$1,250

H 28.5 in W 28.5 in D 1.25 in

Intermission

By Barbara A. Wood

Located in San Francisco, CA

Bush, Georgia Governor Sonny Perdue, Elizabeth Taylor, Hugh Hefner, Jane Seymour, Jerry Lewis, Mickey Rooney, Dick Van Dyke, Dennis Weaver, Art Linkletter, Ron Howard, Gavin MacLeod,...

Category

Late 20th Century Modern Figurative Prints

Materials

Screen

Woman Sitting
Woman Sitting

Barbara A. WoodWoman Sitting, Circa 1990

$1,300

H 37.25 in W 37 in D 1.5 in

Woman Sitting

By Barbara A. Wood

Located in San Francisco, CA

Bush, Georgia Governor Sonny Perdue, Elizabeth Taylor, Hugh Hefner, Jane Seymour, Jerry Lewis, Mickey Rooney, Dick Van Dyke, Dennis Weaver, Art Linkletter, Ron Howard, Gavin MacLeod,...

Category

Late 20th Century Modern Figurative Prints

Materials

Lithograph

Lullabye
Lullabye

Barbara A. WoodLullabye, Circa 1980

$1,200

H 30.75 in W 34.75 in D 1.75 in

Lullabye

By Barbara A. Wood

Located in San Francisco, CA

Bush, Georgia Governor Sonny Perdue, Elizabeth Taylor, Hugh Hefner, Jane Seymour, Jerry Lewis, Mickey Rooney, Dick Van Dyke, Dennis Weaver, Art Linkletter, Ron Howard, Gavin MacLeod,...

Category

Late 20th Century American Impressionist Figurative Prints

Materials

Other Medium

Pensive Woman
Pensive Woman

Barbara A. WoodPensive Woman, Circa 1980

$950

H 30.75 in W 33.5 in D 1.75 in

Pensive Woman

By Barbara A. Wood

Located in San Francisco, CA

Bush, Georgia Governor Sonny Perdue, Elizabeth Taylor, Hugh Hefner, Jane Seymour, Jerry Lewis, Mickey Rooney, Dick Van Dyke, Dennis Weaver, Art Linkletter, Ron Howard, Gavin MacLeod,...

Category

Late 20th Century Modern Figurative Prints

Materials

Other Medium

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph
Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

Party At The Playboy Mansion, Chicago, Estate Edition, Portrait Photograph

By Slim Aarons

Located in Los Angeles, CA

This early 1960s lifestyle photograph, captured by society photographer Slim Aarons, features guests of American publisher Hugh Hefner enjoying themselves at a party being held at th...

Category

1960s Realist Figurative Photography

Materials

Lambda

From the Vargas Portfolio
From the Vargas Portfolio

From the Vargas Portfolio

By Alberto Vargas

Located in Missouri, MO

But late in his life, Vargas was given a second shot at fame and fortune by longtime fan Hugh Hefner. His regular Playboy slot in the 1960s and '70s elevated Vargas to a pinnacle ec...

Category

20th Century Realist Nude Prints

Materials

Lithograph

From the Vargas Portfolio
From the Vargas Portfolio

From the Vargas Portfolio

By Alberto Vargas

Located in Missouri, MO

But late in his life, Vargas was given a second shot at fame and fortune by longtime fan Hugh Hefner. His regular Playboy slot in the 1960s and '70s elevated Vargas to a pinnacle ec...

Category

20th Century Realist Nude Prints

Materials

Lithograph

From the Vargas Portfolio
From the Vargas Portfolio

From the Vargas Portfolio

By Alberto Vargas

Located in Missouri, MO

But late in his life, Vargas was given a second shot at fame and fortune by longtime fan Hugh Hefner. His regular Playboy slot in the 1960s and '70s elevated Vargas to a pinnacle ec...

Category

20th Century Realist Nude Prints

Materials

Lithograph

From the Vargas Portfolio
From the Vargas Portfolio

From the Vargas Portfolio

By Alberto Vargas

Located in Missouri, MO

But late in his life, Vargas was given a second shot at fame and fortune by longtime fan Hugh Hefner. His regular Playboy slot in the 1960s and '70s elevated Vargas to a pinnacle ec...

Category

20th Century Realist Nude Prints

Materials

Lithograph

Playboy Party Slim Aarons Estate Stamped Print
Playboy Party Slim Aarons Estate Stamped Print

Playboy Party Slim Aarons Estate Stamped Print

By Slim Aarons

Located in London, GB

Playboy Party Guests of American publisher Hugh Hefner, December 1961 24 x 20" - paper size Estate Stamped Collection Edition to 150 Photo by Slim Aarons Printed in 2025 Lim...

Category

1960s Modern Color Photography

Materials

Archival Pigment, Color

Body Paint

Byron NewmanBody Paint, 1991

$1,200

H 40 in W 30 in

Body Paint

By Byron Newman

Located in London, GB

Playboy In 1982, whilst Newman and Ariel were in Hollywood on promoting her latest film, Hugh Hefner got in touch and met them at the Playboy Mansion.

Category

1990s Nude Photography

Materials

C Print, Color

'Playboy Party' 1961 Slim Aarons Limited Estate Edition

'Playboy Party' 1961 Slim Aarons Limited Estate Edition

By Slim Aarons

Located in London, GB

'Playboy Party' Guests of American publisher Hugh Hefner, December 1961. Paper Size 24x20 inches / 60 x 50 cm Estate Stamped Collection Edition to 150 Photo by Slim Aarons ...

Category

1960s Modern Color Photography

Materials

Color, Archival Pigment

Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped
Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped

Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped

By Slim Aarons

Located in London, GB

Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped Guests of American publisher Hugh Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 19...

Category

1960s Modern Color Photography

Materials

Archival Pigment

Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped
Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped

Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped

By Slim Aarons

Located in London, GB

Party At The Playboy Mansion 1961 - Slim Aarons Estate Stamped Guests of American publisher Hugh Hefner enjoying themselves at a party being held at the Playboy Mansion, Chicago, 19...

Category

1960s Modern Color Photography

Materials

Archival Pigment

  • 1

Recent Sales

Rorschach Test for Hugh Hefner

Rorschach Test for Hugh Hefner

By Ray Mack

Located in Seattle, WA

RORSCHACH TEST FOR HUGH HEFNER, 2017 oil on canvas 30 x 30 in In her oil paintings, Ray Mack uses formally conventional, erudite practices and themes present in the larger western c...

Category

2010s Contemporary Figurative Paintings

Materials

Oil, Canvas

Hugh Hefner Smiling with Pipe Fine Art Print
Hugh Hefner Smiling with Pipe Fine Art Print

Hugh Hefner Smiling with Pipe Fine Art Print

By Phil Roach

Located in Las Vegas, NV

This black and white photograph features American businessman, magazine publisher and playboy Hugh Hefner smiling and smoking his signature tobacco pipe.

Category

1980s Black and White Photography

Materials

Archival Ink, Archival Paper, C Print, Archival Pigment

Hugh Hefner, Hollywood, 1978

Hugh Hefner, Hollywood, 1978

By Norman Seeff

Located in Beverly Hills, CA

Open Edition Hand-Signed and Numbered by Norman Seeff Additional Sizes Available - 16"x20", 20"x24", 22"x28", 30"x43", 38"x43", 44"x64" Please Inquire for Pricing and Custom Framing ...

Category

1970s Contemporary Color Photography

Materials

Archival Pigment

Hugh Hefner in His Playboy Mansion Fine Art Print
Hugh Hefner in His Playboy Mansion Fine Art Print

Hugh Hefner in His Playboy Mansion Fine Art Print

By W.A. Greenslade

Located in Las Vegas, NV

This stunning color image features American businessman, magazine publisher, and playboy, Hugh Hefner. He was the founder of Playboy and editor-in-chief of the magazine, which he fou...

Category

1970s Color Photography

Materials

Archival Ink, Archival Paper, C Print, Archival Pigment

Hugh Hefner With His Playboy Jet Fine Art Print
Hugh Hefner With His Playboy Jet Fine Art Print

Hugh Hefner With His Playboy Jet Fine Art Print

By W.A. Greenslade

Located in Las Vegas, NV

This stunning color image features American businessman, magazine publisher, and playboy, Hugh Hefner. He was the founder of Playboy and editor-in-chief of the magazine, which he fou...

Category

1950s Color Photography

Materials

Archival Ink, Archival Paper, C Print, Archival Pigment

High Hefner Smiling with Girlfriend Barbi Benton Vintage Original Photograph
High Hefner Smiling with Girlfriend Barbi Benton Vintage Original Photograph

High Hefner Smiling with Girlfriend Barbi Benton Vintage Original Photograph

Located in Las Vegas, NV

This candid black and white capture features the legendary Hugh Hefner smiling with girlfriend Barbara (Barbi) Benton.

Category

1960s Portrait Photography

Materials

Silver Gelatin

Starry Night (diptych)

Starry Night (diptych)

By Marjorie Strider

Located in Lawrence, NY

With the introduction of Hugh Hefner’s Playboy magazine in 1954 the pin-up, now rendered as the “centerfold,” increased in social acceptance and exposure.

Category

2010s Pop Art Figurative Paintings

Materials

Acrylic

LEROY NEIMAN Original PAINTING Signed Oil Pastel Authentic Playboy Artwork SBO
LEROY NEIMAN Original PAINTING Signed Oil Pastel Authentic Playboy Artwork SBO

LEROY NEIMAN Original PAINTING Signed Oil Pastel Authentic Playboy Artwork SBO

By LeRoy Neiman

Located in Bloomington, MN

LeRoy Neiman Original Painting of Playboy Exec Vic Lownes, Custom Framed and Listed with the Submit Best Offer option Title: "Playboy Exec Vic" Medium: Oil and Pastel on Art Paper S...

Category

1960s Post-Impressionist Portrait Paintings

Materials

Oil Pastel

Hugh Hefner Drinking at the "Path" Party Fine Art Print
Hugh Hefner Drinking at the "Path" Party Fine Art Print

Hugh Hefner Drinking at the "Path" Party Fine Art Print

By Phil Roach

Located in Las Vegas, NV

This black and white photograph features American businessman, magazine publisher and playboy Hugh Hefner smiling and smoking his signature tobacco pipe.

Category

1980s Black and White Photography

Materials

Archival Ink, Archival Paper, C Print, Archival Pigment

"Girls of KISS" by Any Freytag for Playboy Legacy Edition 33 of 75
"Girls of KISS" by Any Freytag for Playboy Legacy Edition 33 of 75

"Girls of KISS" by Any Freytag for Playboy Legacy Edition 33 of 75

Located in Los Angeles, CA

KISS and Playboy have a long standing relationship with Simmon's marrying and having a family with Playmate of the Year 1982 Shannon Tweed who was a past flame of Hugh Hefner. The t...

Category

1990s Modern Nude Photography

Materials

Archival Paper

"Tool Time Pam Anderson" Original 20x24 Edition 12 of 75 by David LaChapelle
"Tool Time Pam Anderson" Original 20x24 Edition 12 of 75 by David LaChapelle

"Tool Time Pam Anderson" Original 20x24 Edition 12 of 75 by David LaChapelle

By David LaChapelle

Located in Los Angeles, CA

The Playboy Legacy Collection features 48 museum quality prints hand selected by Playboy founder Hugh Hefner chronicling the history of Playboy magazine since its inception in 1953.

Category

Early 2000s Modern Color Photography

Materials

C Print

"The Nude Marilyn Monroe"  by Earl Moran for Playboy 1946 Edition 33 of 75
"The Nude Marilyn Monroe"  by Earl Moran for Playboy 1946 Edition 33 of 75

"The Nude Marilyn Monroe" by Earl Moran for Playboy 1946 Edition 33 of 75

Located in Los Angeles, CA

Taken in 1946 by renowned pinup artist Earl Moran and then purchased by Playboy who published it in the January 1987 issue as a tribute to Marilyn Monroe written by Hugh Hefner. Ima...

Category

1990s Modern Black and White Photography

Materials

Archival Pigment

The Nude Marilyn Monroe II by Earl Moran for Playboy 1946 Edition 34 of 75
The Nude Marilyn Monroe II by Earl Moran for Playboy 1946 Edition 34 of 75

The Nude Marilyn Monroe II by Earl Moran for Playboy 1946 Edition 34 of 75

Located in Los Angeles, CA

Taken in 1946 by renowned pinup artist Earl Moran and then purchased by Playboy who published it in the January 1987 issue as a tribute to Marilyn Monroe written by Hugh Hefner. Ima...

Category

1990s Contemporary Black and White Photography

Materials

Archival Pigment

Spike Lee’s “Lights, Camera, Fantasy” for Playboy Legacy Edition 34 of 75
Spike Lee’s “Lights, Camera, Fantasy” for Playboy Legacy Edition 34 of 75

Spike Lee’s “Lights, Camera, Fantasy” for Playboy Legacy Edition 34 of 75

By David Levinthal

Located in Los Angeles, CA

A certain number of prints were signed by Hugh Hefner at the launch of collection. The collection was produced and distributed by International Images worldwide.

Category

Early 2000s Modern Black and White Photography

Materials

Archival Paper

The Nude Marilyn Monroe - Playboy Legacy Collection - Signed by Hugh Hefner
The Nude Marilyn Monroe - Playboy Legacy Collection - Signed by Hugh Hefner

The Nude Marilyn Monroe - Playboy Legacy Collection - Signed by Hugh Hefner

Located in New York, NY

It was first published in Playboy in 1987 as part of Hugh Hefner’s tribute to Marilyn for the 25th anniversary year of her death and was featured in the Playboy Legacy Collection in ...

Category

1940s Contemporary Black and White Photography

Materials

Silver Gelatin

Hugh Hefner in His Bedroom Office, Chicago 1961, Black and White Photography
Hugh Hefner in His Bedroom Office, Chicago 1961, Black and White Photography

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 versa. After Hefner purchased several of his short stories for Playboy, Algren said, ...

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Garden Still Life by Doris Berg Statham
Garden Still Life by Doris Berg Statham

Garden Still Life by Doris Berg Statham

By Dea (Doris) Statham Berg

Located in Soquel, CA

In the 1960s, they sold their house in Holmby Hills to Hugh Hefner (now the Playboy Mansion) and retired permanently to Lone Pine.

Category

1970s American Impressionist Still-life Paintings

Materials

Canvas, Oil

Bardot "French Style Girls" oil on canvas 36x60"
Bardot "French Style Girls" oil on canvas 36x60"

Bardot "French Style Girls" oil on canvas 36x60"

By Ceravolo

Located in Southampton, NY

In the left third section of the canvas Ceravolo then painted an oil portrait of Bridget Bardot in his soft focus style which has please his collectors like Elton John, Rod Stewart a...

Category

2010s Pop Art Figurative Paintings

Materials

Canvas, Oil, Acrylic, Oil Crayon

"Stephania Fever" Collage of Woman with Red Lips
"Stephania Fever" Collage of Woman with Red Lips

"Stephania Fever" Collage of Woman with Red Lips

By Derek Gores

Located in Edgartown, MA

In 2017 Gores was commissioned by Playboy Magazine to capture the legacy of Hugh Hefner in a portrait. His works hook you in a luxurious sensory experience with the classic ideals o...

Category

2010s Mixed Media

Materials

Mixed Media

Playing w/ Jagger, acrylic polymer with mica flakes on canvas with archival inks
Playing w/ Jagger, acrylic polymer with mica flakes on canvas with archival inks

Playing w/ Jagger, acrylic polymer with mica flakes on canvas with archival inks

By Ceravolo

Located in Southampton, NY

In addition to those, his paintings are in many influential corporate and private collections, including the three Rock stars mentioned, ELTON JOHN, ROD STEWART and ALICE COOPER, and...

Category

2010s Pop Art Mixed Media

Materials

Canvas, Acrylic Polymer, Mica, Mixed Media, Archival Ink

"Cliffside Catwalk" black and white collage of a woman walking with umbrella
"Cliffside Catwalk" black and white collage of a woman walking with umbrella

"Cliffside Catwalk" black and white collage of a woman walking with umbrella

By Derek Gores

Located in Edgartown, MA

In 2017 Gores was commissioned by Playboy Magazine to capture the legacy of Hugh Hefner in a portrait. His works hook you in a luxurious sensory experience with the classic ideals o...

Category

2010s Abstract Mixed Media

Materials

Canvas, Magazine Paper

"Earthly Stranger" collage of a woman in turquoise and pinks
"Earthly Stranger" collage of a woman in turquoise and pinks

"Earthly Stranger" collage of a woman in turquoise and pinks

By Derek Gores

Located in Edgartown, MA

In 2017 Gores was commissioned by Playboy Magazine to capture the legacy of Hugh Hefner in a portrait. His works hook you in a luxurious sensory experience with the classic ideals o...

Category

2010s Abstract Mixed Media

Materials

Canvas, Magazine Paper

"Art Theory #4" black and white collage of woman holding a martini glass

"Art Theory #4" black and white collage of woman holding a martini glass

By Derek Gores

Located in Edgartown, MA

In 2017 Gores was commissioned by Playboy Magazine to capture the legacy of Hugh Hefner in a portrait. His works hook you in a luxurious sensory experience with the classic ideals o...

Category

2010s Abstract Mixed Media

Materials

Canvas, Magazine Paper

LeRoy Neiman 'Femling - Happy New Year 1992' Original ink & watercolor
LeRoy Neiman 'Femling - Happy New Year 1992' Original ink & watercolor

LeRoy Neiman 'Femling - Happy New Year 1992' Original ink & watercolor

By LeRoy Neiman

Located in Pembroke Pines, FL

While working there he would meet Hugh Hefner, who at the time was working as a copywriter for the department store.

Category

1990s Contemporary Figurative Drawings and Watercolors

Materials

Ink, Watercolor

Greyhounds
Greyhounds

LeRoy NeimanGreyhounds, 1985

Sold

H 52 in W 64 in

Greyhounds

By LeRoy Neiman

Located in New Orleans, LA

In the early 1950s, he would meet a man who changed the trajectory of his career - Hugh Hefner. Shortly after he published his first five issues of Playboy magazine, Hefner invited N...

Category

20th Century Modern Animal Paintings

Materials

Oil, Board

Roma 1954

Art ShayRoma 1954, 2017

Sold

H 20 in W 16 in

Roma 1954

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

Mid-19th Century Contemporary Black and White Photography

Materials

Silver Gelatin

Liz Taylor at the Pump Room, Chicago 1960
Liz Taylor at the Pump Room, Chicago 1960

Liz Taylor at the Pump Room, Chicago 1960

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Field Practice in the Wrigley Vines, Chicago, 1961
Field Practice in the Wrigley Vines, Chicago, 1961

Field Practice in the Wrigley Vines, Chicago, 1961

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

21st Century and Contemporary Contemporary Black and White Photography

Materials

Silver Gelatin

Ali Knocking Out Miteff, Louisville 1961

Ali Knocking Out Miteff, Louisville 1961

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Muddy Waters and His Wife, Geneva, 1951
Muddy Waters and His Wife, Geneva, 1951

Muddy Waters and His Wife, Geneva, 1951

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Thirty Seconds with Johnny Cash, Nashville 1961
Thirty Seconds with Johnny Cash, Nashville 1961

Thirty Seconds with Johnny Cash, Nashville 1961

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Portrait Photography

Materials

Archival Pigment

JFK Surrounded by Ohio Crowd, 1960
JFK Surrounded by Ohio Crowd, 1960

JFK Surrounded by Ohio Crowd, 1960

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Archival Pigment

Rat Pack, Las Vegas 1961

Rat Pack, Las Vegas 1961

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

The Supremes, Supremely Tired, Detroit 1965
The Supremes, Supremely Tired, Detroit 1965

The Supremes, Supremely Tired, Detroit 1965

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Cassius Clay (Ali) In Lockerroom, Louisville 1961
Cassius Clay (Ali) In Lockerroom, Louisville 1961

Cassius Clay (Ali) In Lockerroom, Louisville 1961

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Martin Luther King at Chicago Freedom Rally, Soldier Field, 1966

Martin Luther King at Chicago Freedom Rally, Soldier Field, 1966

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

21st Century and Contemporary Contemporary Color Photography

Materials

Archival Pigment

Bobby Hull, Stanley Cup Playoffs, 1966

Bobby Hull, Stanley Cup Playoffs, 1966

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

21st Century and Contemporary Contemporary Color Photography

Materials

Archival Pigment

Halsted St., Route 66, 1949

Halsted St., Route 66, 1949

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

21st Century and Contemporary Contemporary Black and White Photography

Materials

Silver Gelatin

I Am A Man

Art ShayI Am A Man, 2016

Sold

H 20 in W 16 in

I Am A Man

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Color Photography

Materials

Archival Pigment

James Baldwin, Deerfield, IL 1959, Deerfield Integration Rally
James Baldwin, Deerfield, IL 1959, Deerfield Integration Rally

James Baldwin, Deerfield, IL 1959, Deerfield Integration Rally

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1950s Contemporary Black and White Photography

Materials

Archival Pigment

North Seas Saling
North Seas Saling

North Seas Saling

By LeRoy Neiman

Located in Saint Augustine, FL

He also sketched for magazine fashion ads, but his big break came in 1954 when Hugh Hefner recruited him for Playboy magazine. This began Neiman’s 50-year career as a pinup illustrat...

Category

1970s Contemporary Figurative Prints

Materials

Screen

Bachelor's Needs, 1963

Bachelor's Needs, 1963

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

21st Century and Contemporary Contemporary Color Photography

Materials

Archival Pigment

Maxwell Street 5am, Chicago circa 1957, Black and White Photograph by Art Shay
Maxwell Street 5am, Chicago circa 1957, Black and White Photograph by Art Shay

Maxwell Street 5am, Chicago circa 1957, Black and White Photograph by Art Shay

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Roma, An Italian Gentleman Enjoying a Beautiful Woman, Black & White Photograph
Roma, An Italian Gentleman Enjoying a Beautiful Woman, Black & White Photograph

Roma, An Italian Gentleman Enjoying a Beautiful Woman, Black & White Photograph

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

Mid-19th Century Contemporary Black and White Photography

Materials

Silver Gelatin, Archival Pigment

Welcome Democrats, 1968 Photo Signed

Welcome Democrats, 1968 Photo Signed

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Smoking Dog, Photo Signed
Smoking Dog, Photo Signed

Smoking Dog, Photo Signed

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Blues Great Howlin' Wolf, Chicago 1966, Framed Black and White Photo by Art Shay
Blues Great Howlin' Wolf, Chicago 1966, Framed Black and White Photo by Art Shay

Blues Great Howlin' Wolf, Chicago 1966, Framed Black and White Photo by Art Shay

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

Kid Boxing, 1952, Black and White Photograph by Art Shay, Signed and Framed
Kid Boxing, 1952, Black and White Photograph by Art Shay, Signed and Framed

Kid Boxing, 1952, Black and White Photograph by Art Shay, Signed and Framed

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

20th Century Contemporary Black and White Photography

Materials

Archival Pigment

Muddy Waters and His Wife, Geneva, 1951, Black and White Photography, Framed
Muddy Waters and His Wife, Geneva, 1951, Black and White Photography, Framed

Muddy Waters and His Wife, Geneva, 1951, Black and White Photography, Framed

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1950s Contemporary Black and White Photography

Materials

Silver Gelatin

Smiling Ray Kroc, 1965, McDonald's First Franchise in Des Plaines, IL, Framed
Smiling Ray Kroc, 1965, McDonald's First Franchise in Des Plaines, IL, Framed

Smiling Ray Kroc, 1965, McDonald's First Franchise in Des Plaines, IL, Framed

By Art Shay

Located in Chicago, IL

I’ve been a fan of his work since the early 1950s - before the launch of playboy magazine.” Hugh Hefner “Algren, Terkel, Royko, they gave us a voice.

Category

1960s Contemporary Black and White Photography

Materials

Silver Gelatin

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Hugh Hefner For Sale on 1stDibs

Find the exact hugh hefner you’re shopping for in the variety available on 1stDibs. Find Abstract versions now, or shop for Abstract creations for a more modern example of these cherished works. If you’re looking for a hugh hefner from a specific time period, our collection is diverse and broad-ranging, and you’ll find at least one that dates back to the 20th Century while another version may have been produced as recently as the 21st Century. Adding a hugh hefner 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, brown, gray and more. There have been many interesting hugh hefner examples over the years, but those made by Burt Glinn, Playboy Enterprises, Slim Aarons, Troy Gua and Ray Mack are often thought to be among the most thought-provoking. Artworks like these — often created in silver gelatin print, paper and film — can elevate any room of your home. A large hugh hefner can be an attractive addition to some spaces, while smaller examples are available — approximately spanning 8 high and 8 wide — and may be better suited to a more modest living area.

How Much is a Hugh Hefner?

The price for a hugh hefner in our collection starts at $1,500 and tops out at $8,000 with the average selling for $3,567.