January 1966 Playboy Playmate of the Month is Judy Tyler. Features include an interview of Princess Grace, Going Naked on the Riviera, "The Parisians and the Germans" by Jean-Paul Sartre, The Royal Smut-Hound, plus Playboy's Playmate Review featuring Allison Parks, Pat Russo, Jennifer Jackson, Lannie Balcom, Dianah Willis, Sally Duberson, Patti Reynolds, Maria McBane, Sue Williams, Cay Collier, Hedy Scott and Jessica St. George.

February 1966 Playboy - Sissy Sissy on the cover. Playmate of the Month is Melinda Windsor. Features include an interview of Fredrico Fellini, A Little Lexicon of Love, The History of Sex in Cinema, Part Seven: Europe's Decade of Unbuttoned Erotica, plus The Girls of Rio featuring Molly Peters, Ireny Gomes, Anna Bonaccorsi, Maria Perschy, Lea Rossi, Heloisa Paes Pinto, Adelisia Morris, Lilian Agedelo, Morgana Tavares, Denise Mori, Giddie Vasconcellos, Solange Novelli, Henriette Stein, Joana d'arc de Sonja Dias, Ileana Ghiatza, Flora Romero de Sauzos, Sonia Wollner, Vania Feinand Luely Figueiro, Claudia Alves, Tereza Blanco, Odette Lara, Rozana Tapajos, Miriam Lima, Eline Diolinda Rego, Heloisa da Silva, Annik Deligant and Ann Smyrner.

March 1966 Playboy Playmate of the Month is Pricilla Wright. Features include an interview of Bob Dylan, Ian Fleming's Octopussy, We're Happening All Over, Baby!, plus pictorials of 3 European sex sirens Rossana Podesta, Christiane Schmidtmer, and Shirley Anne Field.

April 1966 Playboy Playmate of the Month is Karla Conway. Features include an interview of George Lincoln Rockwell, The History of Sex in Cinema, Part Eight: Sex Stars of the Thirties, a Behind-the-scenes uncoverage of a dozen years of eye-catching covers and the girls who have adorably adorned Playboy covers, plus a pictorial of Cynthia Maddox.

May 1966 Playboy - Allison Parks Playmate of the Year Allison Parks on the cover and in a pictorial inside. Playmate of the Month is Dolly Read. Features include an interview of Arthur Schlesinger Jr., Why Does My Art Go Boom?, plus a pictorial of Playmate First Class: Jo Collins in Vietnam.

June 1966 Playboy - Mary Warren Mary Warren on the cover. Playmate of the Month is Kelly Burke. Features include an interview of Mike Nichols, The Man and the Myth (Humphrey Bogart), Venus Defiled, plus The Girls of Texas featuring Carol Lee Roberts, Marti Hale, Ann Ford, Lois Johnson, Sharon McDade, Adrea Fleming, Pat Whitmore, Sharon Huff, Alana Collins, Suzanne DuPree, Donna Ritter, Suzie Pat King, Jeanie Froemel, Myles Grant, Judy Johnson, Diane Decker, Joan Nichols, Felicia Thomas, Dina Moor, Maggie Cowart, Sharon Diane Horne, Trisha Adkins, Susan Cunningham, Linda Miller, Nancy Lynn Wallain, Bobbi Ertel, Wanda Walker, Sally Otis Lyman, Shannon O'Quinn, Cathryn Lacey, Linda Davis, Stefani Cole and Heidi Jensen.

July 1966 Playboy - Penny James, Patti Reynolds, Joann Russell, Barbara Shaw and Joey Thorpe Penny James, Patti Reynolds, Joann Russell, Barbara Shaw and Joey Thorpe on the cover (can you find the rabbit?). Playmate of the Month is Tish Howard. Features include an interview of Ralph Ginzburg, On The Secret Service of His Majesty the Queen, "Red China, The U.S. and the U.N." by Max Lerner, and Sean Connery Strikes Again!

August 1966 Playboy - Sissy Sissy on the cover. Playmate of the Month is Susan Denberg. Features include a pictorial of Jane Fonda naked, an interview of H.L. Hunt, The History of Sex in Cinema, Part Nine: War and Peace in Hollywood, plus The Bunnies of Dixie featuring Paula Holcomb, Tonja Mitchell, Sara Atkinson, Barbara Grant, Diana Anton, Hildy Ballard, Mary McFarland Marlene Everett, Peggy Dorris, Jody Duek, Janice Bishop, Jan Roberts, Peaches Coombs, Delilah Graley, Shari Kelley, Carol Leland Shirley Powell,, Lori Schrueger, Mary Jane McGrath, Carol Bruno, Judy Pressley, Lana Brewer, Kim Hester, Abby Mulligan, Gary McQuarrie, Carrie Radison and Bobbi Stephenson.

September 1966 Playboy - Dianne Chandler Playmate of the Month Diane Chandler is on the cover and, of course, inside. Features include an interview of Timothy Leary, It's....Superspa!, The Cold Society, and The History of Sex in Cinema, Part Ten: War and Peace in Europe. Plus, Topless featuring Kay Webster, Carol Doda, Georgia Raft, Lisa Alexander, Stacy Shea O'Hara, Patti Lee Ball, Brandy DeWitt, Carrol Park, Jean Monroe, Jo Kramer, Jocelyn Lane, Blanche Vargas, Kelly Brooke, Kathy Holland Jackie Miller, Kathryn Griggs and Yvonne d'Angers.

October 1966 Playboy - Penny James Penny James on the cover. Playmate of the Month is Linda Moon. Features include an interview of Mel Brooks, Tropic of Cuba, The History of Sex in Cinema, Part Eleven: Sex Stars of the Forties, plus Ann Margaret from The Swinger.

November 1966 Playboy - Sue Batchelor Sue Batchelor on the cover. Playmate of the Month is Lisa Baker. Features include an interview of Norman Thomas, The Sexual Freedom League, History of Sex in Cinema, Part Twelve: The Fifties -- Hollywod Grows Up, plus The Hallucinogenic Hotel Room with Montgomery Clift, Uta Levka, Francissa Gedzek and Ingrid Weber.

December 1966 Playboy - Nancy Gould Nancy Gould on the cover. Playmate of the Month is Sue Bernard. Features include an interview of Sammy Davis Jr., The IBM and I, God Bless the Gentile, "Women as Angels" by Pearl Buck, The Incredible Shrinking Ferrari, The History of Sex in Cinema, Part XIII: The Fifties-Sex Goes International, plus The Girls of Tahiti featuring Partricia Garcia, Mareva Merahi, Myriam Rydge, Sophie Taumihau, Caroline Marthern, Marie Here, Betsy Grigsby, Susie Bright, Maea Flohr, Awlina Tumahai, Annie Thiebaut, Carlosa Lee, Danielle DiLia, Lynn Lambertson, Rosine Copie, Paulette Lieou, Yolande Florh, Etsuko Yashimachi, Marcelle Wong, Mirielle Hart, Neyen Regaud, Vaea Bennett, Cindy Groenendyke, Helene Lee and Annie Typaia.