Every Playboy cover has its own distinction and personality, but there are only a handful of them that people are willing to pay big bucks for. And if you get your hands on a original copy that’s in mint condition, some could be worth a ton someday (hopefully a better investment than beanie babies or your coin collection). From our first cover girl Marilyn Monroe to 1980s sex icon Bo Derek, these are some of the most valued Playboy covers.
Every Playboy cover has its own distinction and personality, but there are only a handful people are willing to pay big bucks for. From our first cover girl Marilyn Monroe to 1980s sex icon Bo Derek, these are some of the most valuable Playboy covers.
Playboy’s premier issue featured Marilyn Monroe, making it a coveted copy. Depending on the condition, this issue can be worth up to $10,000. Hugh Hefner only printed 70,000 copies of this issue, fearing the publication wouldn’t make it past the first issue. First editions are rarer than re-prints and an original is worth a nice chunk of cash. And if you want to know which Marilyn edition you have, the original copies will only have two staples in them while re-prints will have three.
Bo Derek’s March 1980 cover was one of the most popular issues of Playboy and an original copy sold for almost 12,000 in an auction. Her cover shot was photographed by her husband John Derek. Derek is one of the most iconic women of the 1980s and it’s no wonder why the original cover went for so much.
This June 1962 cover sold for almost $4,000 on Christies Auction. Playmate Merissa Mathes’ bikini shot on the cover was photographed by Glen Otto, and it instantly captivated America’s attention when it sold on newsstands. Millions of copies sold even though the cover was pretty controversial for the early 1960s.
The second issue of Playboy in January 1954 was the first issue to be dated. The original copy of the 1954 holiday issue is worth anywhere from $1,850 to $2,650 on Ebay and other collector sites. This is the first cover to feature the iconic rabbit head, making it worth more than other early issues.
The first 15 issues of the magazine are some of the rarest, especially if you are looking for an original and not a reprint. And the third issue of Playboy is no exception. The February 1954 issue featured Yvonne Menard on the cover and is worth anywhere from $700 to $2,000 on Ebay, depending on the quality and grading of the issue.
The March 1954 issue goes anywhere from $600 to $1,500 on Ebay. Most of the 1954 issues are so rare that even the Official Playboy Magazine Store has only three copies in that year for sale. Dolores Del Monte was the Playmate of the Month and Ray Bradbury published part one of his story Fahrenheit 451 in this issue, making it an extremely collectible copy.
Playmate Bettie Page was a 1950s sex icon and had her debut centerfold in January 1955, and any original issue with her centerfold intact is going to be worth some money. The issue can go anywhere from $425 to $750. Ray Bradbury also published his fiction piece The Concrete Mixer in this issue.
The June 1954 issue featured Margie Harrison as Playmate of the Month and had an interview from actor and director Orson Welles. The issue goes between $350 to $1,300 on Ebay and other collector sites. Art Paul, Playboy’s celebrated art director for the first 30 years of the publication, was responsible for overseeing the playful illustrations on the covers, making the 1950s covers collector items.
The September 1954 issue can be worth up to $400. Madeline Castle was the Playmate of the Month and the issue had articles from celebrated jazz musician Louie Armstrong and writer Harry C. Crosby Jr.
The November 1954 issue featured Playmate of the Month Diane Hunter and is worth anywhere from $200 to $1,700. This specific month is a rare find on Ebay and other auction sites.
Honorable Mention: This might be one of the most epic cover photos ever, and even though the actual issue is easy to find and buy, the original cover photo is a collector’s dream item. The cover image of Pamela Anderson and Dan Aykroyd as a conehead in August 1993 had all of America talking, and the cover photo was estimated at $5,000 - $7,000 dollars at Playboy’s “Year of the Rabbit” auction.
Honorable Mention: One of the few men to have the distinction of being on a Playboy cover, Jerry Seinfeld’s cover image on the November 1993 issue was worth some money at Playboy’s “Year of the Rabbit” auction. It was worth $7,000 to $9,000 and yadi yadi yada.. We bet Seinfeld is pretty proud of himself.