January 1988 Playboy Great Issue! Playmate of the Month is Kimberly Conrad. Features include interviews of Arnold Schwarzenegger and Susan Dey, Playboy's Playmate Review with Pamela Stein, Brandi Brandt, Sandy Greenberg, Julie Peterson, Gwen Hajek, India Allen, Carmen Berg, Sharry Konopski, Marina Baker, Kym Paige, Anna Clark and Luann Lee, and a pictorial of Kim Basinger.
February 1988 Playboy - Sandy Greenberg
Sandy Greenberg on the cover and inside. Playmate of the Month is Kari Kennell. Features include interviews of Oliver Stone and Harold Washington, Tyson the Terrible, and hot pictorials of British Page 3 Girls Jackie St. Clair, Maria Whittaker, Carole Anne, Maggie Longhurst, Suzanne Mizzi, Karen Kelly and Gail McKenna.
March 1988 Playboy - Terri Doss Terri Doss on the cover. Playmate of the Month is Susie Owens. Features include interviews of Billy Crystal and Tom Waits, a Lingerie photo special, and a pictorial of Janice Dickinson.
April 1988 Playboy - Vanity Vanity on the cover and inside. Playmate of the Month is Eloise Broady. Features include interviews of Tom Clancy and Harrison Ford, Chinese Women, and music poll results.
May 1988 Playboy - Laurie Carr Laurie Carr on the cover. Playmate of the Month is Diana Lee. Features include interviews of Don King and Teri Garr, and a pictorial of Denise Crosby.
June 1988 Playboy - India Allen Playmate of the Year India Allen on the cover and inside. Playmate of the Month is Emily Arth. Features include interviews of Chevy Chase and Theresa Russell, and a pictorial of Phoebe Legere.
July 1988 Playboy - Cindy Crawford Must-have issue with Cindy Crawford on the cover and in the famous Herb Ritts pictorial inside. Playmate of the Month is Terry Lynn Doss. Features include interviews of Paul Hogan and Judge Reinhold, and international beauties Marta Duca, Luma de Oliveira, Lynn Austin Nathalie Galan, Shannon Lee Long, Stella Kobs, Barbara Ferrat, Jenny Vergidou, Minako Konno, Lucienne Bruinooge and Nuria Pasarisa Dobon.
August 1988 Playboy - Kimberly Conrad Kimberley Conrad on the cover and inside. Playmate of the Month is Helle Michaelsen. Features include interviews of Harvey Fierstein and Harry Edwards, and The Sunshine Girls Lynne Austin, Anna Clark, Brandi Brandt, Sharry Konopski and Pamela Stein.
September 1988 Playboy - Jessica Hahn Jessica Hahn on the cover and inside. Playmate of the Month is Laura Richardson. Features include interviews of Yasir Arafat and Tracey Ullman, and models Stephanie Seymour, Alexandra, Arlene Baxter, Stacey Williams, Lisa Berkley, Keena and Kersti Bowser.
October 1988 Playboy - Terri Lynn Doss Terri Lynn Doss on the cover of the popular college issue. Playmate of the Month is Shannon Long. Features include interviews of Roger Craig and Morton Downey Jr., and Girls of the Southwestern Conference with Kristi Farquhar, Pamela Brewer, Lunnitta Myers, Connie Swinney, Laura Barrington, Dawn Rudkins, Shannon Imle, Lisa Hyde, Carin Blackmon, Tracy Barton, Dawna Rodgers-Early, Joan Moore, Ann Adair, Dawn Perdue, Missy Mitchell, Mary Katherine Brannon, Tia Boretti, Mary Kate, Debra Garcia, Kathrine Albright, Stacey Kawkins, Sharyl Rudin, Sharon Elliott, Tina Bockrath, Mary Plasket, Terri Higgins, alexandra Hathaway, Vanessa Hicks, Laura Pearse, Heather Marion, Caitlin Thomas, Leah Sternbaum, Lisa Jaskolka and Barbara Anne Noelle. Plus, a pictorial of Nancie S. Martin (Playgirl editor in chief).
November 1988 Playboy - Laura Richmond Laura Richmond on the cover. Playmate of the Month is Pia Reyes. Features include interviews of Bruce Willis and John Cleese, Sex in Cinema 1988 with Eddie Murphy, Felicia Taylor, Victoria Dillard, Keenen Ivory Wayans, Anne-Marie Johnson, Richard Dreyfuss, Dan Aykroyd, John Cleese, Timm Robbins, Jessica Rabbit, Bob Hoskins, Marianne Sagebrecht, James Ivory, James Wilby, Hugh Grant, Jean-Luc Godard, Marion Peterson, Valerie Allain, Stratford Johns, Imogen Millais-Scott, Ian Nimmo, Amanda Dole, Thomas Searle, Phoebe Legere, John Altamura, Linnea Quigley, Michael Keaton, Daniel Day-Lewis, Lena Olin, Juliette Binoche, Jacqueline Pearce, Charles Dance, Susan Fleetwood, Murray Head, Greta Scacchi, Catherine Neilsen and Sarah Miles. Plus, the Women of Washington featuring Staci Leigh, Sherrie Echarte, Deenie Hale, Leslie Glass, Michele Edison, Yvette Street, Pamela Pashkovsky, Lesly Brown, Cynthia Curtis, Stacey Lutz, Carolyne Connor, Colleen Cerniglia, Mimi Faillace, Lisa Pittarelli, Gwendolyn Rogers and Cindy Rich.
December 1988 Playboy - Kata Karkkainen Playmate of the Month Kata Karkkainen on the cover and inside. Features include interviews of Cher and Gene Simmons, and Sex Stars of 1988 with Jessica Rabbit, Kevin Costner, Susan Sarandon, Jamie Lee Curtis, Tom Hanks, Tom Cruise, Cher, Sonia Braga, Vanna White, Eddie Murphy, Phoebe Legere, Michael Jackson, Pamela Des Barres, Samantha Fox, Vanessa Williams, Prince, Michael Crawford, Vanity, Linda Kozlowski, Mike Tyson, RObin Givens, Donald and Ivana Trump, Janet Jones, Wayne Gretzky, Greta Scacchi, Virginia Madsen, Brigitte Nielsen, Jessica Hahn, Carrie Leigh and Kimberly Conrad. Plus, Playboy's Playmate Review Susie Owens, Emily Arth, Diana Lee, Kata Karkkainen, Terri Lynn Doss, Eloise Broady, Laura Richmond, Kari Kennell, Shannon Long and Helle Michaelsen.