| Date | Articles |
| Playboy January 1999 | "Last Words
for a Century" by Kurt Vonnegut "Chicken Little Goes Global" by William Greider "Trial Run for New Year's 2000" by John Mariani, Larry Olmsted and Chris Santilli "Kosher Sex" by Rabbi Shmuley Boteach "One More Reality to Go" by Deepak Chopra "Playboy's College Basketball Preview" by Gary Cole "Earth to Universe: Do You Read?" by Michael D. Lemonick. |
| Playboy Febuary 1999 | "The Naked
and The Dead" by A.J. Benza. "Dating Disasters, and How to Avoid Them" by Myles Berkowitz. "Who Can read Your E-Mail?" by Andy Ihnatka. |
| Playboy March 1999 | "Will Your
Relationship Last?" by Craig Vetter. "Go" by Brendan Baber. "So, What Have You Done For Us Lately?" by Keith Olberman. "Playboy Music 1999 -- The Absolute Power of Lauryn Hill" by Kevin Powell. |
| Playboy April 1999 | "Playboy's History of the Sexual Revolution -- Part IX (1980-1989): The Great Repression" by James R. Petersen. |
| Playboy May 1999 | "The Story
of Our Sordid Love" by Janeane Garofalo and Ben
Stiller "Moscow Bites!" by Mark Ames "Playboy's 1999 Baseball Preview" by Leopold Froehlich and George Hodak. |
| Playboy June 1999 | "Lifestyle
Drugs: What's After Viagra?" by Michael Parrish. "DJ Culture" by Timothy Mohr. |
| Playboy July 1999 | "Extreme
Wall Street" by Larry Dubois. "The Manly Secrets of Fly Fishing" by Gary Cole. "Root Rage" by Carl Sherman. "The Best Things I've Done for a Man" by Lori Weiss. "Wrestling Madness" by Mark Husid and William Harlan Pryor. "Sci-Fi TV" by Daniel Radosh. |
| Playboy August 1999 | "Hemingway
Style" by Craig Boreth. "Golf '99" by Ted Johnson. |
| Playboy September 1999 | "E-Crime"
by Logan Hill. "Playboy's Pro Football Forecast" by Rick Gosselin. "Chick Porn" by Lori Seto. |
| Playboy October 1999 | "Encounters
with a Monster" by Peter Klebnikov. "Going Loco" by Katie Roiphe. "Playboy's Pigskin Preview" by Gary Cole. "Holy Sh*t!" by Neil Stebbins. |
| Playboy November 1999 | "Playboy's History of the Sexual Revolution -- Part X (1990-1999): Real Sex" by James R. Petersen. |
| Playboy December 1999 | "Bill
Clinton's Life Lessons" by Christopher Buckley. "A Decade of Scream Queens" by Robert B. DeSalvo. "Tribute to Shel Silverstein" by Jules Feifer. "City Girls" by Amy Sohn. "Playboy's College Basketball Preview" by Gary Cole. "The Duke (Ellington)" by Wynton Marsalis. "Gulf War II" by Scott Ritter. |