| Titles | Order |
| Breathless: Erotica by Kitty Tsui | Sex, 1996 |
| Get in the Van: On the Road With Black Flag (2nd Edition) by Henry Rollins | Music, 1996 |
| In Defense of Mumia by S. E. Anderson | Poetry, 1996 |
| Narrative Corpse: A Chain-Story by 69 Artists! by Art Spiegelman | Graphic Novel, 1996 |
| Pharmako/Poeia: Plant Powers, Poisons, and Herbcraft by Dale Pendell | Drugs, 1996 |
| Pirate Utopias by Peter Lamborn Wilson | Special Recognition/Wildcard Categories, 1996 |
| Race for Justice: Mumia Abu-Jamal's Fight Against the Death Penalty by Leonard Weinglass | Politics, 1996 |
| Saving Graces: Images of Women European Cemeteries by David Robinson | Special Recognition/Wildcard Categories, 1996 |
| A Void by Georges Perec | Fiction, 1996 |
| Censored 1997 (Censored) by Project Censored | Politics, 1997 |
| Death Scenes: A Homicide Detective's Scrapbook by Sean Tejaratchi | Special Recognition/Wildcard Categories, 1997 |
| Distorture (Black Ice Books) by Rob Hardin | Fiction, 1997 |
| Everything I Know I Learned on Acid by Coco Pekelis | Drugs, 1997 |
| The Guide to Getting It On! (The Universe's Coolest and Most Informative Book About Sex) by Paul Joannides | Sex, 1997 |
| Home in Three Days, Don't Wash (Lingo Books) by Linda Smukler | Poetry, 1997 |
| I Need More by Iggy Pop | Music, 1997 |
| InterCourses: An Aphrodisiac Cookbook by Martha Hopkins | Special Recognition/Wildcard Categories, 1997 |
| Nothing But The Girl; The Blatant Lesbian Image by Susie Bright | Art/Photo, 1997 |
| The Palm of My Heart by Davida Adedjouma | Kids, 1997 |
| Real Americans Admit: "The Worst Thing I'Ve Ever Done" by Ted Rall | Graphic Novel, 1997 |
| Transgender Warriors : Making History from Joan of Arc to Dennis Rodman by Leslie Feinberg | Nonfiction, 1997 |
| Devil Babe's Big Book of Fun by Isabel Samaras | Art/Photo, 1998 |
| In Awe by Scott Heim | Fiction, 1998 |
| In Daddy's Arms I Am Tall: African Americans Celebrating Fathers by Javaka Steptoe | Kids, 1998 |
| The Joint Rolling Handbook by Bobcat Press | Drugs, 1998 |
| Minimum Wage: Book 2: The Tales of Hoffman by Bob Fingerman | Graphic Novel, 1998 |
| Monk by Laurent De Wilde | Music, 1998 |
| NASA/Trek: Popular Science and Sex in America by Constance Penley | Special Recognition/Wildcard Categories, 1998 |
| Ono Ono Girl's Hula by Carolyn Lei-Lanilau | Nonfiction, 1998 |
| Original Sin: The Visionary Art of Joe Coleman by Jim Jarmusch | Special Recognition/Wildcard Categories, 1998 |
| Queer Dog: Homo/Pup/Poetry (Queer Dog) by Gerry Gomez Pearlberg | Poetry, 1998 |
| Red Meat: A Collection of Red Meat Cartoons From the Secret Files of Max Cannon by Max Cannon | Special Recognition/Wildcard Categories, 1998 |
| The Ultimate Guide to Anal Sex for Women by Tristan Taormino | Sex, 1998 |
| The Zinn Reader: Writings on Disobedience and Democracy by Howard Zinn | Politics, 1998 |
| The Beauty of Fetish by Midori | Art/Photo, 1999 |
| Burning in Paradise by Michael Madsen | Poetry, 1999 |
| Cunt: A Declaration of Independence Expanded and Updated Second Edition by Inga Muscio | Nonfiction, 1999 |
| Dancing With the Skirt (Teletubbies) | Special Recognition/Wildcard Categories, 1999 |
| Dark Alliance: The CIA, the Contras, and the Crack Cocaine Explosion by Gary Webb | Politics, 1999 |
| Facetasm : Creepy Mix-And-Match Book of Face Mutations by Charles Burns | Kids, 1999 |
| Leather Daddy and the Femme by Carol Queen | Fiction, 1999 |
| Lords of Chaos: The Bloody Rise of the Satanic Metal Underground New Edition by Michael Moynihan | Music, 1999 |
| Maurice Vellekoop's ABC Book: A Homoerotic Primer by Maurice Vellekoop | Sex, 1999 |
| My Gender Workbook: How to Become a Real Man, a Real Woman, the Real You, or Something Else Entirely by Kate Bornstein | Self Improvement, 1999 |
| Steven Cerio's ABC Book: A Drug Primer by Steven Cerio | Drugs, 1999 |
| The Story of Colors/La Historia de Los Colores: A Bilingual Folktale from the Jungles of Chiapas by Subcomandante Marcos | Special Recognition/Wildcard Categories, 1999 |
| Street Posters and Ballads by Eric Drooker | Graphic Novel, 1999 |
| Dori Stories: The Complete Dori Seda by Dori Seda | Special Recognition/Wildcard Categories, 2000 |
| From Girls to Grrlz : A History of Women's Comics from Teens to Zines by Trina Robbins | Art/Photo, 2000 |
| Fucked Up & Photocopied: Instant Art of the Punk Rock Movement by Bryan Ray Turcotte | Music, 2000 |
| The Future of History: Interviews with David Barsamian by Howard Zinn | Nonfiction, 2000 |
| High Times Presents Paul Krassner's Pot Stories for the Soul by Paul Krassner | Drugs, 2000 |
| I Was a Teenage Dominatrix: A Memoir by Shawna Kenney | Sex, 2000 |
| Mental Hygiene: Better Living Through Classroom Films 1945-1970 by Ken Smith | Special Recognition/Wildcard Categories, 2000 |
| My New York Diary by Julie Doucet | Graphic Novel, 2000 |
| No More Prisons by William Upski Wimsatt | Politics, 2000 |
| The Outlaw Bible of American Poetry by Alan Kaufman | Poetry, 2000 |
| Po Man's Child by Marci Blackman | Fiction, 2000 |
| Aunt Mary Jane's Baking With Pot (High Times Classics) by Mary Jane | Drugs, 2001 |
| Deviant Desires: Incredibly Strange Sex by Katharine Gates | Sex, 2001 |
| Jimmy Corrigan: The Smartest Kid on Earth by Chris Ware | Graphic Novel, 2001 |
| The Neal Pollack Anthology of American Literature: The Collected Writings of Neal Pollack by Neal Pollack | Fiction, 2001 |
| The Ralph Nader Reader by Ralph Nader | Politics, 2001 |
| The Real Rules for Girls by Mindy Morgenstern | Kids, 2001 |
| The Strange Case of Edward Gorey by Alexander Theroux | Nonfiction, 2001 |
| Strange Fruit: The Biography of a Song by David Margolick | Music, 2001 |
| This is Blythe by Gina Garan | Art/Photo, 2001 |
| 9-11 by Noam Chomsky | Politics, 2002 |
| Cunt-Ups by Dodie Bellamy | Poetry, 2002 |
| Devil's Advocate: The Art of Coop by Chris Cooper | Art/Photo, 2002 |
| Fast Food Nation: The Dark Side of the All-American Meal by Eric Schlosser | Nonfiction, 2002 |
| Hardcore from the Heart: The Pleasures, Profits And Politics of Sex in Performance (Critical Performances) by Annie Sprinkle | Sex, 2002 |
| Junkie Love by Phil Shoenfelt | Drugs, 2002 |
| Palestine by Joe Sacco | Graphic Novel, 2002 |
| Strange Stories for Strange Kids (Little Lit, Book 2) by Art Spiegelman | Kids, 2002 |
| This Too Can Be Yours by Beth Lisick | Fiction, 2002 |
| We Owe You Nothing by Daniel Sinker | Music, 2002 |
