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Playboy’s 37 Best Playmate of the Year Covers

A look at Playboy's finest.

Classics September 20, 2026
Playboy’s 37 Best Playmate of the Year Covers
Eugena Washington by Jason Lee Parry, 2016

Being a Playmate of the Month is a coveted honor, one that many women dream of, but relatively few will have. And if that monthly title is so sought after, being Playmate of the Year is essentially the equivalent of being crowned queen.

Well, here we have the covers that 37 of our queens from years past graced, spanning Playboy‘s earliest years to our most recent. We have Jo Collins, our 1965 Playmate of the Year, who eventually travelled to Vietnam during the war at the request of soldiers. There’s Debra Jo Fondren, whose luscious locks are instantly iconic. And of course, Jenny McCarthy and Anna Nicole Smith, two of our most famous Playmates.

Whether they’re your old favorites or you’re meeting new faces, enjoy a look back at some of Playboy‘s finest.

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