In December 1953, 27-year-old Hugh Hefner published the very first "Playboy" magazine. This first edition of "Playboy" was 44-pages long and had no date on its cover because Hefner wasn't sure there would be a second edition. In that first run, Hefner sold 54,175 copies of "Playboy" magazine at 50 cents each. The first edition sold so well because Marilyn Monroe was the "Sweetheart of the Month" (which was thereafter termed "playmate").

Peter Sellers, actor and comedian extraordinaire was the first man to appear on the cover of "Playboy", in April 1964.

There are hilarious photos of him with actress Karen Lynn, in that famous issue which is a parody of the lovers in James Bond’s “You Only Live Twice” and then "Dracula" to follow.

The second was Burt Reynolds, in October 1979. The other men who have been on the cover of "Playboy" are Steve Martin, Jerry Seinfeld, Donald Trump, Dan Aykroyd, Leslie Nielsen, Gene Simmons, Seth Rogan and Bruno Mars.

More Info: en.wikipedia.org