December 1953: Marilyn Monroe (Issue #1)

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The one that launched it all.

Monroe’s debut cover and centerfold make this the crown jewel of Playboy magazines. Even mid-grade copies can command serious cash; high-grade or signed copies are in another galaxy.

Depending on condition, this issue could be worth anywhere from $500 to several thousand dollars. An extremely rare, 9.4-graded sold for $120,000 at Heritage Auctions in 2023. 

January 1955: Bettie Page (Playmate of the Month)

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Pin-up royalty. Page’s centerfold is catnip for vintage collectors and one of the most chased 1950s issues.

Bettie was an American model and kept copies of this issue sell for tens of thousands of dollars.

September 1985: Madonna

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Photos from her pre-fame days turned into one of Playboy’s most controversial (and collectible) ‘80s releases.

Clean copies move fast. Recently, a crisp edition sold for $2,000.

January 1954: First Dated Issue + First Rabbit

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This is the second-ever issue of Playboy, and featured a couple of firsts:

Actress Margie Harrison became the magazine’s first official Playmate of the Month and this issue’s cover included an actual date, which Hef omitted on issue #1.

The now-iconic bunny made its debut in this issue as well, looking more cartoonish than the sleek and sexy logo we’ve come to know.

Clean copies here land around $2,000 to $4,000.

May 1987: Vanna White

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Try to wheel this Wheel of Fortune icon.

America’s puzzle queen shocked everyone and created a perennial top-seller among ‘80s magazines when she posed in 1987.

Cool little nod to Wheel of Fortune in the issue’s title.

October 1989: Pamela Anderson (first cover)

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Pam became a recurring cover legend, but the first one is the one collectors zero in on.

Early Pam covers in great condition are reliably liquid.

A mint first-Pam issue sold for $3,500 in 2021.

March 1992: Anna Nicole Smith (as Vickie Smith)

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Before the name change and the reality-TV era, this centerfold lit the fuse. Her PMOY run makes early appearances extra collectible.

December 1995: Farrah Fawcett

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A megastar finally doing Playboy in the mid-’90s? Instant grail for a lot of fans. Clean copies still pull premium interest.

January 1995: Drew Barrymore

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A very ‘90s culture flashpoint. First-run copies kept crisp (no creases, no stains, tight spine) can perform surprisingly well.

June 1962: Merissa Mathes

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Merissa Mathes pulled double duty in ’62—cover model and Playmate of the Month (June)—before landing a string of film/TV roles through the decade.

The photoshoot turned heads, but it was the cover crop (framed tightly on her bikini line) that sent censors clutching pearls and copies flying off shelves. Collectors still chase it hard; one example reportedly hammered for nearly $4,000 at auction in recent years, with price riding heavily on condition and grading.

August 1993: Pamela Anderson & Dan Aykroyd (Coneheads Cover)

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Welcome to the multi-cover era. 

Pamela Anderson—who racked up 13 Playboy covers—shares this one with Dan Aykroyd in full Coneheads getup, making it one of the weirder (and more collectible) ’90s variants.

At Playboy’s “Year of the Rabbit” auction back in 2010, a clean copy of this edition was pegged in the $5,000–$7,000 range. As always, grade is king: sharp corners, tight spine, and no sun-fade.

September 2009: Heidi Montag (Original Mud Cover)

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The Hills star took over the September ’09 issue, slicked in mud with a hand-drawn bunny on her midsection—a memorable visual that aged into a collector magnet.

At Playboy’s “Year of the Rabbit” auction, the original cover photo was estimated at $5,000+, with value swinging on condition and provenance (sharp corners, tight spine, no scuffs = $$$).