Marilyn Monroe Cover (Composite).

Playmate of the Month
Jamie Bergman photographed by Stephen Wayda.

Interview
Michael Crichton by John Rezek and David Sheff.

20 Questions
Kirstie Alley by David Rensin.

Features
"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.

Thierry Mugler's Sex Couture
Models photographed by Thierry Mugler.

Sex Stars of the Century
Lillian Muller, Dolly Parton, Mata Hari, Blaze Starr, Dede Lind, Katarina Witt, Carroll Baker, Fay Wray, Diana Dors, Marilyn Chambers, Lynda Carter, Terry Moore, Julie Newmar, Louise Brooks, Jacqueline Bisset, Loni Anderson, Joan Crawford, Shannon Tweed, Janet Pilgrim, Linda Evans, Gene Tierney, Lene Horne, Gypsy Rose Lee, Liv Lindeland, Kathy Ireland, Diana Rigg, Cynthia Myers, Janet Jackson, Irish McCalla, Paulina Porizkova, Cheryl Tiegs, Lili St. Cyr, Anna Nicole Smith, Ava Gardner, Sally Rand, Michelle Pfeiffer, Stephanie Seymour, Patti McGuire, Christie Brinkley, Tempest Storm, Barbi Benton, Claudia Schiffer, Barbara Eden, Vanna White, Theda Bara, Greta Garbo, Christa Speck, Suzanne Somers, Brooke Shields, Donna Michelle, Candy Barr, Halle Berry, Angie Dickinson, Catherine Deneuve, Mae West Hedy Lamarr, Josephine Baker, Candy Loving, Clara Bow, Joan Collins, Vanessa L. Williams, Heather Locklear, Linda Lovelace, Madonna, Elke Sommer, June Wilkinson, Bettie Page, Marlene Dietrich, Mamie Van Doren, Jane Fonda, Lana Turner, Stella Stevens, Grace Kelly, Sharon Stone, Evelyn Nesbit, Gina Lollobrigida, Elle MacPherson, Jane Russell, Ursula Andress, Kim Novak, Betty Grable, Farrah Fawcett, Jenny McCarthy, Anita Ekberg, Jean Harlow, Ann-Margret, Kim Basinger, Bo Derek, Rita Hayworth, Pamela Anderson, Brigitte Bardot, Sophia Loren, Elizabeth Taylor, Cindy Crawford, Raquel Welch, Jayne Mansfield and Marilyn Monroe (not all previously named are nude).

Interviews
Adam Sandler by David Sheff.
"Checking in with Adam Sandler" by Kevin Cook.

Profile
"Pat Robertson: The Holy Terror" by Mark Bowden.

20 Questions
"The Motley Fool (David and Tom Gardner)" by Warren Kalbacker.

Feature
"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.

NFL Cheerleaders
Bonnie-Jill Laflin, Lisa Marie, Kelli Huckins, Pamela Wellham, Carrie Swoboda, Vaneeda Trukowski, Rachel Kerr, Carla McFarlan and Leah-Marie Duryea.

Interview
Drew Carey by Heather Dean.

Profile
"Rudy Rules (Rudy Giuliani)" by Paul Schwartzman.

20 Questions
Gerry Adams by Morgan Strong.

Features
"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.

Interview
Nick Nolte by Lawrence Grobel.

Profile
"Chazz (Calogero Palminteri)" by Kevin Cook.

20 Questions
David Schwimmer by Robert Crane.

Features
"Playboy's History of the Sexual Revolution -- Part IX (1980-1989): The Great Repression" by James R. Petersen.

Spring Break
Wyndi Pinckney, Missa Blanton, Erin Wilson, Shanon Snider, Monica Petschulat, Michelle Guice, Michelle Grafwallner, Lee Ann Koskie, Brenda Archiquette, Colleen Evilsizer, Emily Bowling, Mikyla Chernoff, Julie Drain, Melanie Starr, Jammie Parker, Stephanie Lindsey, Melissa Cordeiro, Tonya Millard, Alissa Paterson, Jessica Enlers, Jennifer Terra, Brandi Sawyer, Nicole Kosich and Leslie Thomas.

Interview
David Spade by David Rensin.

Profile
"The Exterminator Rep (Tom DeLay)" by Molly Ivins.

20 Questions
Ashley Judd by Robert Crane.

Features
"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.

Playmates on Safari
Karin Taylor, Jami Ferrell and Rachel Jean Marteen photographed by Richard Fegley.

Playmate of the Month
Kimberly Spicer photographed by Richard Fegley.

Interview
Samuel L. Jackson by Michael Fleming.

Profiles
"His Hipness the Mayor (Willie Brown)" by Burr Snider.
Deborah Harry by Glenn O'Brien.

20 Questions
Christina Applegate by Robert Crane.

Features
"Lifestyle Drugs: What's After Viagra?" by Michael Parrish.
"DJ Culture" by Timothy Mohr.

Interviews
Barney Frank by David Sheff.
"Drinking, Screwing, Defying -- The World According to David Wells" by Mark Ribowsky.

20 Questions
Michael Moore by Warren Kalbacker.

Features
"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.

Girls of Hawaiian Tropic
Brooke Richards (cover and inside), Jennifer Braff, April Abraham, Nicole Carter, Gemma Sutton, Renee Slaughter, Patti O'Donell, Michell Damm, Carrie Flaska, Jennifer DeYonker, Tenniel Cacayan, Kalin Olson, April Morgan, Tanna Holly, Jennifer Canale, Michelle Vaden, Charlotte Arlt, Angie Chittenden, and Johan Berube photographed by Arny Freytag and Stephen Wayda.

Interview
Albert Brooks by Bill Zehme.

Profile
"My Adventures with Stanley Kubrick" by Ian Watson.

20 Questions
Lucy Liu by Robert Crane.

Features
"Hemingway Style" by Craig Boreth.
"Golf '99" by Ted Johnson.

Lara Croft (cover and inside) photographed by Richard McLaren.

Interview
Chris Rock by David Rensin.

Profile
Moss Man by Kent Youngblood.

20 Questions
Jeri Ryan by David Rensin.

Features
"E-Crime" by Logan Hill.
"Playboy's Pro Football Forecast" by Rick Gosselin.
"Chick Porn" by Lori Seto.

Playmate of the Month
Jodi Ann Paterson photographed by Arny Freytag.

Interviews
Kevin Spacey by Michael Fleming.
Matthew Perry by David Rensin.

20 Questions
Joe Morgan by Robert S. Wieder.

Features
"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.

Girls of the PAC 10
Salome Meneses, Megan Hershberger, Kristine Roberts, Dawn Delgado, Lauren Sinclair, Heather Bean, Rebecca Newell, Anne Endrikat, Sarah Prince, Rachael Klein, Irina Isshiki, Tatiana Becker, Alisha Taylor, Gima Jesse, Stacy Robinson, Sarah Pickard, Laura Delisa, Jennifer Lee, Laurie Chapman, Jasmine Masuda, Rachel Howe, Kristie Halsey, Nikol Litera, Michele Barrios, Brooke Williams, Summer Morgan, Lori Ligouri, Lacey Ballantyne, Vanessa Cabe, Michelle Michaels, Alexa Savalos, T.J. Metcalf, Naomi Lee, Carolee Bass, Ashley Marie, Lily Cervantes, Brandi Shaeffer, Erica Andrejko, Natasha Paris and Jaime Stevens photographed by David Chan, David Macey and David Rams.

Interviews
Jesse Ventura by Lawrence Grobel.
Sheryl Crow by Mark Ribowsky.

Profile
David Duval by Carl Vigeland.

20 Questions
George Jones.

Features
"Playboy's History of the Sexual Revolution -- Part X (1990-1999): Real Sex" by James R. Petersen.

Sex in Cinema 1999
Tom Cruise and Nicole Kidman, Scott Carson and Maria Ford, Anna Kaminskaia and Susan Featherly, Cristian Bale and Emily Watson, Jeannie Pepper and Lexington Steele, Shannon Elizabeth (not nude), Jason Biggs (not nude), Nina Hoss (slutty pose, not nude), Chris Stafford and Tina Holmes (under sheets), Karyn Dwyer and Christina Cox (under sheets), Gwen Somers (with a female), Shyra DeLand Chase Conville and Brad Bartam (threesome), Claudia Schiffer and Robert Downey Jr. (seductive scene, not nude), Alison Eastwood and Neill Bary, Suzanne Cryer and George Newbern, Julia Roberts and Hugh Grant (covered by sheets), Sophie Marceau and Pierce Brosnan (not nude), Diane Lane and Viggo Mortensen (seductive, his back exposed), Kate Winslet (breast exposed), Sergio Assisi and Gabriella Pession, Rocco Siffredi and Caroline Ducey, Natacha Regnier and Gregoire Colin.

Playmate of the Month
Brooke Richards photographed by Stephen Wayda.

Interview
Ben Affleck by Bernard Weinraub.

20 Questions
Gina Gershon by Robert Crane.

Features
"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.

Naomi Campbell (cover and inside, totally nude) photographed by David Lachapelle.

Sex Stars 1999
Ricky Martin, Jennifer Lopez, Catherine Zeta-Jones, Elizabeth Hurley, Sophie Marceau, Hugh Grant, Shania Twain, Julia Roberts, Keri Russell, Heather Kozar, Denis Richard, Rene Russo, Rebecca Romijn-Stamos, Cameron Diaz, Laetitia Casta, Nikki Schieler, Caprice, Tom Cruise, Nicole Kidman, Pamela Anderson, Pierce Brosnan, Mia St. John, Angelina Jolie, Halle Berry, Sean Connery, Nell McAndrew, Charlize Theron, Will Smith, Heather Graham and Rena Mero (some previously named are nude).