Playmates of the Month
Carol and Darlene Bernaola photographed by Arny Freytag.

Interview
Hugh M. Hefner by Bill Zehme.

20 Questions
Rupert Everett by David Rensin.

Features
"The Future of Vice" by Christopher Buckley
"That Was the Century That Was" by Robert S. Wieder
"The Office of the Future" by Scott Adams
"Porn-O-Rama!" by Al Franken
"Cities on the Moon" by Ray Bradbury
"Will Women Change?" by John Gray
"Justice in the 21st Century" by Johnnie Cochran
"1950: When Nothing Was the Same" by David Halberstam
"There's No Space Like Home" by Syd Mead
"Money 2000" by Harry S. Dent Jr.
"Unheralded Innovations of the 20th Century" by Bob Sloan
"Global Shock" by James Hoge.

Mini-Hef
Verne Troyer (not nude) and nude models photographed by Arny Freytag.

Centerfolds of the Century
Shae Marks, Jean Bell, Shauna Sand, Julie Woodson, Susan Bernard, Nikki Schieler, Elsa Sorensen, Janet Jupo, Martha Smith, Fawna MacLaren, Shanon Johansen, Ola Ray, Brandi Brandt, Jennifer Jackson, Roberta Vasquez, Sondra Theodore, Lonny Chin, Jami Ferrell, Dolly Read, Lisa Baker, Melinda Windsor, Mara Corday, Brittany York, Julie Lynn Cialini, Joyce Nizzari, Penny Baker, Corinna Harney, Heidi Becker, Azizi Johari, Victoria Valentino, Connie Kreski, Patricia Farinelli, Avis Kimble, Alana Soares, Dahm Triplets, Monique St. Pierre, Christine Maddox, Anna-Marie Goddard, Van Breeschooten Twins, Bonna E'Errico, Barbara Edwards, Kathy Shower, Ellen Stratton, Connie Mason, Angela Dorian, Karen Price, Stacy Sanches, Linda Gamble, Terri Welles, Petra Verkaik, Lisa Matthews, Jaime Bergman, China Lee, Allison Parks, Eve Myer, Marguerite Empey, Collinson Twins, Karen McDougal, Gwen Wong, Janice Pennington, Julie McCullough, Bebe Buell, Yvette Vickers, Kimberly McArthur, Karen Valez, Renee Tenison, Cyndi Wood, Marianne Gravatte, June Cochran, Heather Kozar, Nancy Cameron, Marilyn Lange, Erika Eleniak, Donna Edmondson, Lisa Winters, Victoria Silvstedt, Liv Lindelind, Claudia Jennings, Karen Christy, Marilyn Cole, DeDe Lind, Debra Jo Jondren, Christa Speck, Jo Collins, Anna Nicole Smith, Lillian Muller, Kimberley Conrad, Stella Stevens, Shannon Tweed, Patti McGuire, Cynthia Myers, Donna Michelle, Dorothy Stratten, Jenny McCarthy, Dancy Loving, Pamela Anderson, Bettie Page, Jayne Mansfield, Janet Pilgrim and Marilyn Monroe.

Playboy's Playmate Review
Natalia Sokolova, Rebecca Scott, Jennifer Rovero, Kimberly Spicer, Stacy Fuson, Alexandria Karlsen, Jaime Bergman, Tishara Cousino, Cara Wakelin, Kristi Cline, Jodi Ann Paterson and Brooke Richards.

Interview
Jeff Bezos by David Sheff.

Profile
"Don't Cross John McCain" by Amy Silverman.

20 Questions
Steven Van Zandt by John Rezek.

Features
"Rage" by Erin Zammett.
"Crime Fighters" by Jack Maple.
"A Lifetime of Sex" by Bruce Jay Friedman.
"Robert Schimmel's Money Shot" by Christopher Napolitano.

Wet Dreams
Kalin Olson, Kelly Monaco and Victoria Fuller photographed by Richard Fegley and Al Giddings.

Interviews
Jon Stewart by David Rensin.
Jesse II (Jesse Ventura) by Lawrence Grobel.

20 Questions
Cindy Margolis by David Rensin.

Features
"Let's Go Racing" by Michael Jordan.
"The Return of the Private Eye" by Dick Lochte.
"How to be an Indie Movie Mogul" by Ted C. Fishman.
"City Girls -- Episode 2: Sticky Fingers" by Amy Sohn.

Mardi Gras 2000
Elizabeth Cox, Katherine Houghton, Christina Serrano, Amanda Thersher, April Oden, Michelle Conner, Kori Adams, Holly Guidry, Karina Mitchell, Katalina Verdin, Catherine Collins, Shannon Leahy, Laurie Wallace, Tiffany Buecher, Angela Seibert, Roxanne Galla and Nicole Narian photographed by Gen Nishino.

Playmate of the Month
Brande Roderick photographed by Stephen Wayda.

Interviews
Rowland Evans and Robert Novak by David Sheff.
Big Biz (Limp Biskit) by Alison Lundgren.

20 Questions
Barry White by Julie Bain.

Features
"Love and Death in the Desert" by Peter Alson.
"Songs That Changed the World" by Charles M. Young.
"I Want My MP3" by Beth Tomkiw.
"Bavarian Creme" by Ken Gross.
"Bring on the Bandwidth" by Ted C. Fishman.

Bijou Phillips (cover) photographed by Ellen Von Unwerth.

Interview
Pete Rose by Mark Ribowsky.

20 Questions
Michael Palin by Warren Kalbacker.

Features
"Tantric Sex" by Amanda Green.
"The Best Bars in America" by Gerry Dawes.
"Showstoppers" by James R. Petersen.
"Don't Worry, We Only Kill Each Other" by Jamie Malanowski.
"Playboy's 2000 Baseball Preview" by Leopold Froehlich and George Hodak.
"In Defense of Pete Rose" by Bill James.

Playmate of the Month
Shannon Stewart photographed by Stephen Wayda.

Interview
Trey Parker and Matt Stone by Steve Pond.

20 Questions
James Coburn by David Rensin.

Features
"The New Superathlete" by Allen Barra.
"Rules for the Perfect Relationship" by Steven Slon.
"How to Survive a Night in Tijuana" by Robert B. DeSalvo.
"Little Annie Fanny" by Ray Lago and Don Wimmer.
"Surfing the Web for Contraband" Mark Ehrman.

"The Bond Files" with photos of Famke Janssen, Sophie Marceau, Honor Blackman, Teri Hatcher, Izabella Scorupco, Jane Seymour, Kim Basinger, Maud Adams, Babara Carrera, Daniela Bianchi, Maryam d'Abo, Ursula Andress and Corinne Clery (some partially nude).

Interview
George Clooney by Bernard Weinraub.

20 Questions
Carson Daly by Warren Kalbacker.

Features
"Don't Pet the Donkey" by Christopher Napolitano.
"Still Rockin'" by Nancy L. Prichard.
"One Guy, Four Ex-Girlfriends, Lots of Wine" by Scott Bindley.

Nice Chalupas!
Asia Mendez, Jon Secada (not nude), Miriam Gonzalez, Paolo Aravena, Monica Mendez, Amelia Garduno, Nina Santoyo-Bradley, Lianna Grethel, Shantell Lugo, Lucia Loza, Yvette Garcia, Iveth Cortez, Nenna Quiroz, Rebecca Ramos, Gerine Coronado, Katalina Verdin and Sonia Flores photographed by Richard Fegley.

Interviews
John Malkovich by Kristine McKenna.
"There's Something About Macy (Gray)" by Alison Lundgren.

20 Questions
Aimee Mann by Robert Crane.

Features
"Millionaires" by Jamie Malanowski.
"You Don't Look A Day Over 150, Want to Screw?" by Kathleen Sharp.
"City Girls: Boys and Toys" by Amy Sohn.
"The Nerve of Erv!" by Ray Bradbury.

Interview
Jennifer Lopez by Michael Fleming.

20 Questions
Seth Green by Robert Crane.

Features
"Making Book On Campus" by Erin Zammett.
"Calerie Morpheus" by Robert B. Desalvo.
"Dr. Jokes" by David Rensin.
"Playboy's Pro Football Forecast" by Rick Gosselin.
"You Don't Have to be Gay to Get Laid But it Helps!" by Glenn O'Brien.
"Digital Wearables" by Timothy Mohr.

Interview
Bob Costas by Diane K. Shah.

20 Questions
Michael Johnson by Ken Stephens.

Features
"Casualty in the War on Drugs" by Jim Dwyer
"Eleven Things You Did'nt Want to Know About Spinal Tap" by Chip Rowe
"Playboy's Pigskin Preview" by Gary Cole
"Dave's Garage: Round 2" by David Stevens.

Spring Break Lasts All Year at Jamaica's Adults-Only Resort of Heat and Hedonism
Photography by George Georgiou and Mark Deward Harris.

Girls of Conference USA
Erica Wally, Nicole Ratliff, Sarah Coleman, Dannette Stanley, Jennifer Lyn Harris, Amy Barnett, Terah Chin, Natalie Trask, Shannon Kirby, Anna Harris, Jessica Carmichael, Nicole Reno, Elizabeth Edmondson, Nicolette Reeves, Stephanie Heinrich, Brittany Leigh, Eva Renee, Heather Malone, Julie Geoghegan, Jessica Mauch, Cara Waronicki, Erin Stubbe, Alica Goldman, Amy Warner, Mandy Fisher, Linda Hubacova, Brooke Moore, Jennifer Cross, Ami Holley, Sidra McCain, Jennifer Johnston, Skylar Brobson, Nicole Washington, Lauren Marie, Jennifer Boehm, Erica Jasen, Dana Sestokas, Helene Kersey, Genevieve Almodovar, Tiffany Sneed, Laura Langdon, Vanessa Rains, Tiffany Richmond, Sabrina Trevino, Amppy Basa, Shiley Coverdale and Carmen Mendes photographed by David Mecey, Mizuno and David Rams.

Interview
Ben Stiller by David Rensin.

20 Questions
Neil Labute by Bernard Weinraub.

Features
"The Biker Wars" by James R. Petersen
"Deep Inside DVD" by Jason Buhrmester
"Snake as in Jake" by Ashley Jude Collie
"Twenty Things I Learned in Sex Class" by Lou Paget
"Russian Girls" by Matt Taibbi.

Sex In Cinema 2000
Mena Suvari, Ralph Fiennes, Deborah Unger, Julianne Moore, Lucy Marie Jenner, Renee Rea, Michael Ball, Anna Davidoff, Natacha Regnier, Jeremie Renier, Nancy O'Neil, Jesse Coleman, Tracy Smith, Nancy O'Brien, Christian Bale, Cameron Diaz, Billy Crudup, Holly Hunter, Sofie Grabol, Anders Berthelsen, Rachel Griffiths, Maurice Morgan, Julia Kruis, Mia and Christopher Johnston, Cathy Moriarty, Eddie Cibrian, Clea DuVall, Sean Penn, Samantha Morton, Vicoria Hamilton, Alessandro Nivola, Allan Corduner, Sakina Jaffrey, James Wilby, Catalina Larranaga, Jamaica Charley, Louis D'Alto, Hilary Swank, Chloe Sevigny, John Standing, Matthew Delamere and Toni Collette (not all previously named are nude).

Interview
Drew Barrymore by Michael Fleming.

20 Questions
Jakob Dylan by Kristine McKenna.

Features
"Cuba Fever" by Achy Obejas
"Slick Willy -- A Fond Farewell" by Jamie Malanowski
"Saturday Night Lewd" by Paul Krassner
"The X-Presidents" by Robert Smigel and Adam McKay
"Phone Sex" by Richard Lewis
"Playboy's College Basketball Preview" by Gary Cole and David Kaplan
"Celebrity Christmas Carols" by Robert S. Wieder.

Women Down Under
Michelle Johnston, Racheal Ingram, Samantha Bolton, Imogen Bailey, Gloria Howearth, Radana Povolny, Bree Maddox, Melissa Hallstrom, Joanne Ziegeler, Lucy Halliday, Jane Redman, Natasha Buttle, Simone Suthiwart-Narueput, Kelly Anne Walls, Divini Bean, Gayna Rowling, Olena Karpina and Tisha Eve Williams photographed by Arny Freytag.