Photos: Hugh Hefner in His Pre-Pajama Years

There’s a giant cloud of mystery (and straight-up confusion) that follows Hugh Hefner wherever he treads in his velvet bedroom slippers. The wealthy founder of Playboy has lapped up the attention since he created the publication in 1953, by throwing extravagant fetes in his mansion, juggling multiple girlfriends at once, and cementing his image as a smoking-robe-clad octogenarian never without a “bunny” in his arms.

But in Taschen’s upcoming six-volume anthology dedicated to Playboy’s first 25 years and its founder, aptly titled Hugh Hefner’s Playboy, readers get an intimate, illustrated look at Hefner before he became the over-the-top men’s magazine mogul he is today. Included in the 3,506 pages: cartoon drawings from Hef’s childhood and early career; famous interviews published in the magazine with Martin Luther King and John Lennon; writing by Jack Kerouac, Ray Bradbury, and Gore Vidal; personal photos; and Hefner’s own autobiography — in which he recounts his youth, cartoonist years, romantic relationships, and more. The books will be hitting shelves in September. Until then, click through the slideshow to see a different side of Hugh Hefner and the many ladies (and famous companions) who stood by his side.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Cover of Volume Two.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Hefner with Dot Novak.  

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Hefner with a new Cadillac Eldorado, Chicago, 1955.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Hefner with Joyce Nizzari.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Hefner at work, with Cynthia Maddox, Chicago, 1958.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Hugh Hefner (right) with his brother, Keith, his father, Glenn, and his mother, Grace, in Chicago, 1967.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Barbi Benton and Hefner, Miami, 1970.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Hefner and Benton at Playboy Mansion West, 1970.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Barbi Benton and Hefner, with Jet Bunnies, Los Angeles, 1970.

Photo: 2013 Playboy Enterprises International Inc. / Taschen

Arnold Schwarzenegger, Hefner, and Wilt Chamberlain, Playboy Mansion West, 1977.