Results for “Playboys”

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Steve Kaufman Original Marilyn Monroe Oil Painting On Canvas Signed Playboy Art: This lot includes:Gallery COA. In-house shipping available (insurance and international shipping for an additional charge).Artist: STEVE KAUFMANTitle: Marilyn MonroeMedium: Oil Painting on CanvasSize:

4 days Left

Steve Kaufman Original Marilyn Monroe Oil Painting On Canvas Signed Playboy Art

Est. $500-$750

Playboy Magazine Collection of 30 Vintage Issues: This lot includes a collection of 30 vintage Playboy magazines featuring a wide range of iconic cover designs spanning multiple decades. The group includes issues showcasing notable pop culture moment

Feb 19, 2026

Playboy Magazine Collection of 30 Vintage Issues

Williamson Auction Gallery

Est. $200-$400

Jennifer Wolcott Signed 8x10 Hand Signed Photo Playboy Playmate PSA COA: Jennifer Wolcott Signed 8x10 Hand Signed Photo Playboy Playmate PSA COA

5 days Left

Jennifer Wolcott Signed 8x10 Hand Signed Photo Playboy Playmate PSA COA

Deluxe Auctioneers

Est. $200-$300

Playboy Magazine April 1992 Playmate Cady Cantrel: This lot is coming from the estate of a collector in RI. We have included a quality scan to show it's actual condition. This lot is located in Boca Raton, Fl and its shipment will be made directly by

Feb 19, 2026

Playboy Magazine April 1992 Playmate Cady Cantrel

Est. $30-$50

1 - Playboy March 1999 & 5 - Tongue Magazine (by Gene Simmons): Artist: Unknown Title: 1 - Playboy March 1999 & 5 - Tongue Magazine (by Gene Simmons) Medium: Magazines Limited Edition: Art Dimensions: 11.0 x 9.0 x 4.0 inch ARTIST BIO: Source

5 days Left

1 - Playboy March 1999 & 5 - Tongue Magazine (by Gene Simmons)

Michael's Gallery

Est. $100-$200

Restored Set of Six Jens Risom Model C140 Playboy Chairs in Canary Yellow Velvet: Restored Set of Six Jens Risom Model C140 Playboy Chairs in Canary Yellow Velvet Introducing a stunning set of six Mid-Century Modern Model C140 "Playboy" chairs, designed by the renowned Jens Risom,

Feb 19, 2026

Restored Set of Six Jens Risom Model C140 Playboy Chairs in Canary Yellow Velvet

Est. $5,109-$6,641

Vintage Playboy Dec 1969 - Xmas Issue, Joe Namath Int. Gloria Root: This lot is coming from the estate of a collector in RI. We have included a quality scan to show it's actual condition. This lot is located in Boca Raton, Fl and its shipment will be made directly by

Feb 19, 2026

Vintage Playboy Dec 1969 - Xmas Issue, Joe Namath Int. Gloria Root

Est. $30-$50

Hugh Hefner Signed Playboy 3x5 Index Card Authenticated by Beckett: Hugh Hefner Signed Playboy 3x5 Index Card Authenticated by Beckett This authentic 3x5 index card is personally signed by Hugh Hefner, the legendary founder of Playboy. It is slabbed and authenticated

3 days Left

Hugh Hefner Signed Playboy 3x5 Index Card Authenticated by Beckett

Est. $845-$1,098

Hugh Hefner Autographed 8x10 Playboy Photo with Beckett COA: Hugh Hefner Autographed 8x10 Playboy Photo with Beckett COA This original 8x10 photograph features the iconic Hugh Hefner, signed by the legendary founder of Playboy. The autograph is authenticated by

2 days Left

Hugh Hefner Autographed 8x10 Playboy Photo with Beckett COA

Est. $689-$895

Cindy Crawford - Playboy- Photograph by Herb Ritts Re-Printed: This lot is coming from the estate of a collector in RI. The dimensions are Approx. 11" x 8.5". We have included a quality scan to show it's actual condition. This lot is located in Boca Raton, Fl and

Feb 19, 2026

Cindy Crawford - Playboy- Photograph by Herb Ritts Re-Printed

Est. $30-$50

LaToya Jackson Sean Penn Julia Roberts Playboy Magazine Nov 1991: This lot is coming from the estate of a collector in RI. We have included a quality scan to show it's actual condition. This lot is located in Boca Raton, Fl and its shipment will be made directly by

Feb 19, 2026

LaToya Jackson Sean Penn Julia Roberts Playboy Magazine Nov 1991

Est. $30-$50

Pussy Cat Short Stemmed Glasses & Playboy Mug: Pussy Cat Short Stemmed Glasses & Playboy Mug. This lot includes: (3) The Pussycat Short Stemmed Glasses. Each is approx 3" x 3" x 5" and together they weigh 1.24lb. (1) Club Playboy

Feb 23, 2026

Pussy Cat Short Stemmed Glasses & Playboy Mug

Rapid Estate Liquidators and Auction Gallery

Est. $80-$160

Vintage 1995 Playboy Music Festival Shirt 100% Cotton White: Vintage 1995 Playboy Music Festival Shirt 100% Cotton White Experience a piece of music history with this original vintage 1995 Playboy Music Festival Shirt. This true vintage shirt features striking

Feb 17, 2026

Vintage 1995 Playboy Music Festival Shirt 100% Cotton White

Est. $325-$422

Hugh Hefner Autographed Baseball Playboy JSA Certified: Hugh Hefner Autographed Baseball Playboy JSA Certified This is a pre-owned Hugh Hefner signed baseball, featuring an authentic signature verified by James Spence Authentication (JSA). The ball is a co

2 days Left

Hugh Hefner Autographed Baseball Playboy JSA Certified

Est. $1,261-$1,639

Vintage 1960s-70s Playboy & more Adult magazines, 20+ issues, some wear from age: Appears to be in fair to good shape. The piece measures approx inches. See pics. E-4880 *Oversized shipping may apply*

Vintage 1960s-70s Playboy & more Adult magazines, 20+ issues, some wear from age

Crawford Family Auctions LLC

Est. —

$20(1 bid)

RARE Complete Set Five Playboy Magazines Featuring Anna Nicole Smith: Complete Set Collection of five Playboy magazines featuring Anna Nicole Smith. Includes the Playmate of the Year issue and other issues highlighting her career with Playboy. Each magazine is sealed in

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RARE Complete Set Five Playboy Magazines Featuring Anna Nicole Smith

Williamson Auction Gallery

Jens Risom Mid-Century Modern Sculpted Walnut Playboy Lounge Chair, 1960s: A gorgeous mid-century modern "Playboy" lounge chair or club chair By Jens Risom USA, 1960s Sculpted solid walnut frame, with original tan upholstery. Measures: 22.25"W x 23"D x 31.75"H. Seat height 1

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Jens Risom Mid-Century Modern Sculpted Walnut Playboy Lounge Chair, 1960s

Liberty & 33rd Furniture Co.

Oil painting Playboy Pink Igor Konovalov: Title: Oil painting Playboy Pink Igor Konovalov Description: Kon 12 *** ABOUT THIS PAINTING *** * TITLE: "Playboy part 1" * ARTISTS: Igor Konovalov * SIZE: 135x110 cm/'53.14x43.30 inches' * MEDIUM: oi

2026

Oil painting Playboy Pink Igor Konovalov

Chairish Auctions

Est. $7,700-$11,000

Buy Now for $2,530.00

RARE Lot of 14 - Full Set - Playboy Magazines Featuring Pamela Anderson: Complete set Collection of 14 Playboy magazines featuring Pamela Anderson on the cover. Issues include June 1998 (Babes of Baywatch), July 1992, January 1996, November 1994, November 1993, August 1993

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RARE Lot of 14 - Full Set - Playboy Magazines Featuring Pamela Anderson

Williamson Auction Gallery

Playboy Magazines June and July 1998 Featuring Baywatch and Jenny McCarthy: Playboy magazines from June and July 1998 The June 1998 issue is a collector's special titled The Babes of Baywatch, while the July 1998 issue features Jenny McCarthy on the cover Both magazines are p

Playboy Magazines June and July 1998 Featuring Baywatch and Jenny McCarthy

Legacy Auction & Realty

Est. —

$10

Leroy Neiman Original Ink Drawing Signed Playboy Playmate 21 Club Framed Artwork: This lot includes:Gallery COA & free domestic shipping (*insurance and international shipping for an additional charge)Artist: LeRoy NeimanTitle: Playboy Playmate at 21Medium: Ink DrawingSize: 11" x 8

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Leroy Neiman Original Ink Drawing Signed Playboy Playmate 21 Club Framed Artwork

Playboy Magazines December 1995 and January 1996 Featuring Farrah Fawcett and Pamela Anderson: Two Playboy magazines: December 1995 edition featuring Farrah Fawcett and January 1996 edition featuring Pamela Anderson Both magazines are in clear protective covers with visible date and pricing ($5

Playboy Magazines December 1995 and January 1996 Featuring Farrah Fawcett and Pamela Anderson

Legacy Auction & Realty

Est. —

$10

Shelby Chesnes PLAYBOY In Person Signed Photo: Photo size is 8x10. Shelby Chesnes in person signed photo. Shelby Chesnes rose to popularity as a Playboy model who became Miss July 2012 by the magazine. In 2014, Playboy Magazine awarded her the tit

Feb 22, 2026

Shelby Chesnes PLAYBOY In Person Signed Photo

EB Autographs & Collectibles

Est. $75-$100

Todd White - Playboy Bunnies: Artist: Todd White Title: Playboy Bunnies Dimensions: 12.5in. by 9.5in. Edition: Unique Original one of a Kind Artwork Medium: Hand Drawing on Paper Condition:

Feb 19, 2026

Todd White - Playboy Bunnies

Dane Fine Art Gallery

Est. $4,000-$6,000

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