Playboy January 1959

Playboy February 1959

Playboy's Playmate of the Month
Eleanor Bradley photographed by Ron Vogel

Covergirl
Ardie Scott (not nude)

Features
"The Buttondown Boys at Creespville High" by Stewart P. Brown
"A Fist Full of Money" by Henry Slesar and Jay Folb
"The Sensible Man" by Avram Davidson
"Girls in Their Lairs" (pictorial)

Playboy March 1959

Playboy's Playmate of the Month
Audrey Daston photographed by Lawrence Schiller

Covergirl
Unidentified Model (not nude)

Features
"Names in Lights" by Leonard Lyons
"Silverstein in Spain" cartoons by Shel Silverstein
"The Horror of It All" by Hollis Alpert and Charles Beaumont
"I Love You, Miss Irvine" by John Wallace

Playboy April 1959

Playboy's Playmate of the Month
Nancy Crawford photographed by Barbara and Justin Kerr

Features
On The Scene: Dave Lambert, Jon Hendricks and Anni Ross, Sidney Poitier, Oliver Treyz
"With All Due Respect" by Fred McMorrow
"Nasty" by Fredric Brown
"What's Become of Your Creature?" by Herbert Gold

Playboy May 1959

Playboy's Playmate of the Month
Cindy Fuller (First Jewish-American Playmate) photographed by Bunny Yeager

Features
"Dealers Wild" by T.K. Brown III
"The Girl Had Been Around" by E.S. Jensen
"Triplication" by Robert Sheckley
Playboy's Playmate Of The Month In the Swim

Playboy June 1959

Playboy's Playmate of the Month
Marilyn "Charlie" Hanold photographed by Bruno Bernard

Features
"The Origins of the Beat Generation" by Jack Kerouac
"The Voyage of the Peanut" by Harvey Jacobs
"Waste Not, Want Not" by John Atherton
"The Mann Act" by Alan Holmes

Playboy July 1959

Playboy's Playmate of the Month
Yvette Vicers photographed by Russ Meyer

Features
"The Little World of Oscar Levant" by Maurice Zolotow
"No Fire Burns" by Avram Davidson
"The Coffee Houses of America" by Jim Morad
"The Incredible Adventures of Dino" by Herbert Gold

Playboy August 1959

Playboy's Playmate of the Month
Clayre Peters photographed by Frank Eck

Covergirl
Unknown (not nude)

Features
"Cult of the Aged Leader" by Ralph Ginzburg
"The Sender of Letters" by Herbert Gold
"Silverstein Among the Arabs" cartoons by Shel Silverstein
"OK, So I?m a Cookooboo" by Charles Hamblett

Playboy September 1959

Playboy's Playmate of the Month
Marianne Gaba photographed by Lawrence Schiller

Covergirl
Legs in Yellow Shoes (not nude)

Features
"The Miss America Joke" by Oliver Kinkaid
"The Taste of Fear" by Hugh G. Foster
"A Song in His Pocket" by Barry B. Spacks
"The World of Heart's Desire" by Robert Sheckley

Playboy October 1959

Playboy's Playmate of the Month
Elaine Reynolds photographed by Frank Eck

Features
"Loving Couple" by Edward Wellen
"A Very Good Sidewalk Story" by Herbert Gold
"The Alky Era" by Ken Purdy
"Svengali of the Silver Screen" by Al Morgan

Playboy November 1959

Playboy's Playmate of the Month
Donna Lynn photographed by Frank Bez

Covergirl
The Playboy Bunny (not nude)

Features
"A Cry From the Penthouse" by Henry Siesar
"The Joan Club" by William Link and Richard Levinson
"O Debt, Where is Thy Sting?" by Carlton Brown
"Beads From Other Times and Places" pictorial

Playboy December 1959

Playboy's Playmate of the Month
Ellen Stratton photographed by William Graham

Features
"Before the Road" by Jack Kerouac
"And Now, A Word From the Sponsor" by Al Morgan
"The Legend of Don Juan" by J.A. Gato
Building a Better Brigitte (The Famous French Sex Kitten Has Brought Forth a Litter)