10 Most Collectible Playboy Magazines

Hugh Hefner’s death at 91 leaves us with a lot of questions. How did he build such an empire? How many women did he sleep with? And what was with all those silly captain’s hats?

While we can’t answer those questions easily, here’s a fun one: What are the 10 most collectible Playboy magazines? These would be the special editions that people were able to purchase that featured special models, interviews or celebrities.

Of course, the first issue of Playboy, published in 1953, with Marilyn Monroe on the cover and a price of fifty cents, would be a collectible edition now. It sells for as much as $10,000 on eBay (but hey, free shipping!). However, this would not be an issue most people would be able to get their hands on now. What issues would be easier to collect and obtain now?

1. January, 2000. The theme for this issue was 100 most beautiful women of the 20^th Century. This made this issue a true collector’s item.
2. January, 1979. This was Playboy’s 25th Anniversary issue. Candy Loving was featured as their centerfold. This can be a hard issue to find in mint condition.
3. January, 1981. This is a special issue because it is rich in content. The cover features model Barbara Bach. There is an interview with John Lennon and Yoko Ono and a fictional piece by Stephen King inside this issue.
4. June, 1957. This issue was known as Playboy’s cufflinks cover. It was all white, except for a pair of bunny cufflinks that sat in the right hand corner.
5. March, 1964. This issue was special because of the interview with philosopher Ayn Rand.
6. October, 1977. Barbara Streisand graced the cover and gave the magazine an interview.
7. December, 1968. Actress Cynthia Myers graced the cover and was also Playmate of the Month.
8. March, 1968. Jane Fonda was featured in pictures within this issue.
9. January, 1986. This issue was known as Andy’s Warhol’s cover.
10. July, 1988. Cindy Crawford graced the cover of this issue.

Many of the above issues of Playboy can still be purchased from $3.00 to $5.00. Many people who specialize in collectibles think these issues could jump as much $30 to $40 an issue, if they are kept in mint condition.

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