| 0 | In This Issue We Sock It To Pokemon, The Practice, The Class Of 2000 | cover | 1 | pencils: Richard Williams; inks: Richard Williams; colors: Richard Williams | Alfred E. Neuman; Pets.com Sock Puppet |
| 1 | The Malpractice | comic story | 5 | script: Josh Gordon; pencils: Mort Drucker; inks: Mort Drucker | Dylan McDermott [as Bibby Donutt]; Steve Harris [as Hugh Gene Yank]; LisaGay Hamilton [as Tribecca Wishbone]; Michael Badalucco [as Jumbo Berloophole]; Lara Flynn Boyle [as Hellion Grumble]; Kelli Williams [as Lindseed Doll]; Maria Sokoloff [as Loosely Hatchett]; Camryn Manheim [as Ellenbore Frapp]; |
| 2 | High School Yearbook Inscriptions You're Sure to See | photo story | 3 | script: Kenny Byerly; pencils: James Warhola; inks: James Warhola | |
| 3 | A New Millennium Update to Mad's Table of Little Known and Very Useless Weights, Measures and Distances | comic story | 2 | script: J. Prete; pencils: Bob Staake; inks: Bob Staake | |
| 4 | The Downside of Online Shopping | comic story | 2 | script: John Caldwell; pencils: John Caldwell; inks: John Caldwell; letters: John Caldwell | |
| 5 | Monroe and… the Foreign Exchange Student | comic story | 4 | script: Anthony Barbieri; pencils: Bill Wray; inks: Bill Wray | Monroe; Mom; Grandpa; Hung Lo; Dylan; Sponsor Family |
| 6 | The Pokemon Collectors Hall of Fame | comic story | 2 | script: Mike Snider; pencils: R. J. Matson; inks: R. J. Matson | Stuart Stuttermeyer; Derek Chan; G. Gordon Bloodsucker III; Louie Santini; Sister Mary Angelica; Jimmy Johnson; Jeremy Quince |
| 7 | Bumper Stickers That Reflect Real School Life | comic story | 2 | script: Jeff Kruse; pencils: Paul Coker; inks: Paul Coker | |
| 8 | The Ex-Files | comic story | 1 | script: Duck Edwing; pencils: Duck Edwing; inks: Duck Edwing | |
| 9 | Wes Craven | text story | 3 | script: Andrew J. Schwartzberg; pencils: Bill Wray; inks: Bill Wray | Wes Craven; Drew Barrymore; Neve Campbell; David Arquette; Courtney Cox Arquette; Jennifer Love Hugetop |
| 10 | One Fine Day in the Animal Testing Lab | comic story | 1 | script: Michael Gallagher; pencils: Paul Coker; inks: Paul Coker | |
| 11 | The Lighter Side of... | comic story | 4 | script: Dave Berg; pencils: Dave Berg; inks: Dave Berg | Roger Kaputnik |
| 12 | The Swedish Mattress That Made Sleeping Obsolete! | text story | 1 | script: Dick DeBartolo; pencils: James Warhola; inks: James Warhola | Aged Khristmastree |
| 13 | Mad's Commencement Address for the Class of 2000 | comic story | 2 | script: Mike Snider; pencils: Tom Bunk; inks: Tom Bunk | |
| 14 | - | comic story | 2 | script: Peter Kuper; pencils: Peter Kuper; inks: Peter Kuper | Black Spy; White Spy |
| 15 | Mad Anagrams | comic story | 1 | pencils: Sam Sisco; inks: Sam Sisco | Dennis Rodman; Howard Stern; The Mars Polar Lander; George Bush; Robert Dole; Princess Diana; Calista Flockhart; Brandi Chastain |
| 16 | A Mad Look at Parents | comic story | 4 | script: Sergio Aragonés; pencils: Sergio Aragonés; inks: Sergio Aragonés | |
| 17 | Still More Obituaries for Merchandising Characters | text story | 3 | script: Frank Jacobs; pencils: Scott Bricher; inks: Scott Bricher | Juan Valdez; Taco Bell Chihuahua; Maytag Repairman; Betty Crocker; Little Caesar; Pets.Com Sock Puppet |
| 18 | Mad's Celebrity Cause-Of-Death Betting Odds | comic story | 1 | script: Mike Snider; pencils: Hermann Mejía; inks: Hermann Mejía | Regis Philbin |
| 19 | What Rocker Is Everyone Sick of Listening to? | illustration | 1 | script: Al Jaffee; pencils: Al Jaffee; inks: Al Jaffee | Mick Jagger; Fred Durst; Elton John; Courtney Love; Steven Tyler; Bob Dylan; Bruce Springsteen; Gene Simmons; John Rocker |
| 20 | Magnetic Personality | comic story | 1 | script: Michael Gallagher; pencils: Tom Bunk; inks: Tom Bunk | |