Playboy: 50 Years of Playmates

Playboy: 50 Years of Playmates

Playboy: 50 Years of Playmates

September 14, 2004
Directed by
Scott Allen

Every Playmate in Playboy's 50-Year history all in one collectors edition.

Last Updated: April 13, 2026

Cast

Hugh Hefner as Self - Editor-In-Chief

Hugh Hefner

Self - Editor-In-Chief

Pamela Anderson as Self - Miss February 1990

Pamela Anderson

Self - Miss February 1990

Marilyn Monroe as Self (archive footage)

Marilyn Monroe

Self (archive footage)

Shannon Stewart as Self - Miss June 2000

Shannon Stewart

Self - Miss June 2000

Carmella DeCesare as Self - Miss April 2003

Carmella DeCesare

Self - Miss April 2003

Dorothy Stratten as

Dorothy Stratten

Claudia Jennings as

Claudia Jennings

Sondra Theodore as

Sondra Theodore

Cynthia Myers as

Cynthia Myers

Kimberley Conrad as

Kimberley Conrad

Eloise DeJoria as

Eloise DeJoria

Barbara Moore as

Barbara Moore

Colleen Shannon as

Colleen Shannon

Deborah Driggs as

Deborah Driggs

Jaclyn Dahm

Image Gallery

Gallery image from pEiCJUm3zbe695hVo4AnQUGmkAp.jpg

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