The Cover Men:
Murray Christmas, 1998; America’s first Black Santa, Sonny Liston (the photo shoot has a great backstory here); The Power Stance, 2000
The “Esky” Covers:
For those not familiar with “Esky,” he is Esquire’s little mustachioed mascot.
I will put a page break here, because the next photos are semi-NSFW.
This is one of my favorite covers not only for the adorable scene on the front, but it hides something… A full size pullup pinup calendar! I need to find one of these on eBay or something because pinups are one of my loves, and Miss July is a Vargas Girl I have tattooed on my back! 50 Cents for this at the time of print, oh golly!