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PLAYBOY MAGAZINE — MAY 1999 — VOL. 46, NO. 5
A particularly interesting late-1990s issue of Playboy featuring Charlize Theron, David Spade, Ashley Judd, Ben Stiller, Janeane Garofalo, and May 1999 Playmate Tishara Lee Cousino.
WHY THIS ISSUE IS COLLECTIBLE
The standout attraction is the Charlize Theron cover and pictorial. Published in May 1999, this issue captures Theron during a fascinating point in her career: she was already attracting major Hollywood attention through films including The Devil’s Advocate and Mighty Joe Young, but this was several years before her Academy Award-winning performance in Monster made her one of Hollywood’s most acclaimed actresses.
An especially interesting piece of history surrounds the pictorial itself. The photographs published by Playboy originated earlier in Theron’s modeling career, before she had become a major Hollywood star. That gives the feature an unusual place in her career history and makes the issue considerably more interesting today than an ordinary celebrity appearance from 1999.
The issue contains a substantial Charlize Theron feature photographed by Guido Argentini, with both color and black-and-white photography. Contemporary collector references describe the feature as a multi-page pictorial, while the magazine itself presents it as “Mighty Young Theron Conquers Hollywood’s Wild Kingdom.”
PLAYMATE OF THE MONTH — TISHARA LEE COUSINO
May’s Playmate is Tishara Lee Cousino, photographed by noted Playboy photographer Arny Freytag.
Cousino was a Las Vegas native with a background in dance, including ballet, jazz and hip-hop. Her May 1999 appearance became the beginning of a continuing association with Playboy; she subsequently appeared in Playboy special editions and videos for several years. Her original May 1999 centerfold is present in this copy.
PLAYMATES ON SAFARI
Another major pictorial is “Playmates on Safari,” photographed in Africa and featuring Playmates Karin Taylor, Jami Ferrell and Rachel Jean Marteen. The elaborate location photography makes this one of the issue’s more distinctive pictorial features and very different from a conventional studio shoot.
PLAYBOY INTERVIEW — DAVID SPADE
The issue’s full Playboy Interview features David Spade, then firmly associated with the enormously successful 1990s comedy generation surrounding Saturday Night Live. The conversation covers his career, dating, his departure from SNL and life following the death of his friend and frequent co-star Chris Farley.
20 QUESTIONS — ASHLEY JUDD
Ashley Judd receives Playboy’s “20 Questions” treatment. In 1999 she was in the midst of her rise as a leading Hollywood actress, making this another particularly period-specific celebrity feature.
BEN STILLER & JANEANE GAROFALO
The issue also includes “The Story of Our Sordid Love” by Janeane Garofalo and Ben Stiller. Both were important figures in the alternative-comedy and film culture of the 1990s, adding another strong piece of period entertainment history to the magazine.
A SNAPSHOT OF 1999
What makes this issue especially fun to revisit more than 25 years later is how thoroughly it captures its moment.
Alongside Theron, Spade, Judd, Stiller and Garofalo is Playboy’s 1999 Baseball Preview, a feature on Moscow, technology and lifestyle coverage, and political commentary by syndicated columnist Molly Ivins, who profiles then-Congressman Tom DeLay.
The combination of Hollywood, politics, sports, technology, humor and photography makes the magazine a genuine cultural time capsule of America at the end of the 20th century.
Even the advertising contributes to that period character — including the full-page 1999 Smirnoff “All Vodka. No Pretense.” advertisement shown in the listing photographs.
MAJOR CONTENTS INCLUDE:
• Charlize Theron — featured pictorial, photography by Guido Argentini
• Tishara Lee Cousino — May 1999 Playmate of the Month, photography by Arny Freytag
• David Spade — Playboy Interview
• Ashley Judd — 20 Questions
• Janeane Garofalo & Ben Stiller — “The Story of Our Sordid Love”
• Playmates on Safari — Karin Taylor, Jami Ferrell & Rachel Jean Marteen
• Molly Ivins profile of Congressman Tom DeLay
• Playboy’s 1999 Baseball Preview
• Moscow Bites! — Mark Ames
• Joshua Redman fashion feature
• The Shadow Trees — fiction by Brendan DuBois
• Dave’s Garage — David Stevens
• Gotta Have It
• Little Annie Fanny
• Plus Playboy’s regular departments, cartoons, commentary, lifestyle features and vintage advertising
CONDITION
Pre-owned original May 1999 Playboy in Very Good condition for its age.
Interior pages shown in the photographs remain clean and attractive with strong color. Binding is secure. Tishara Lee Cousino’s centerfold is present and is attached.
Exterior shows normal vintage handling and storage wear, including light edge/corner wear and creasing, with a very small tear along the upper edge of the front cover near the PLAYBOY masthead (see cover). The back cover shows some light age-related spotting/handling marks.
Please review all photographs carefully. They show the actual magazine you will receive and form an important part of the condition description.
A great addition to a Playboy collection, Charlize Theron collection, celebrity-magazine collection, or collection of late-1990s pop-culture memorabilia.
Prompt shipping after payment. Magazine will be securely packaged to help protect it during transit.
