| 0 | The 20 Dumbest People, Events, and Things of 1999! | cover | 1 | pencils: Drew Friedman; inks: Drew Friedman | |
| 1 | The Supremos | comic story | 6 | script: Arnie Kogen; pencils: Mort Drucker; inks: Mort Drucker | James Gandolfini [as Tummy Supremo]; Lorraine Bracco [as Dr. Jennifer Morphine]; Nancy Marchand [as Livid Supremo];Dominic Chianese [as Uncle Juniper]; Agent Finochiaro; Edie Falco [as Carvella Supremo]; Father Philander; Daffy Duck (cameo); Jamie-Lynn Siglar [as Muddow Supremo]; Lucy Van Pelt (came |
| 2 | Monroe and... Christmas | comic story | 4 | script: Anthony Barbieri; pencils: Bill Wray; inks: Bill Wray | |
| 3 | Absurd Man of Alcatraz | comic story | 1 | script: Duck Edwing; pencils: Duck Edwing; inks: Duck Edwing | |
| 4 | The Mad 20 Dumbest People, Events, and Things of 1999 | comic story | 16 | script: Russ Cooper, Charlie Kadau, Joe Raiola, David Shayne, Scott Maiko, Desmond Devlin; pencils: Hermann Mejía, Irving Schild, AP/Wide World, Jack Syracuse, Scott Bricher, Keith Seidel; inks: Hermann Mejía, Irving Schild, AP/Wide World, Jack Syracuse, Scott Bricher, Keith Seidel | |
| 5 | The Sick Sense | comic story | 5 | script: Dick DeBartolo; pencils: Angelo Torres; inks: Angelo Torres | Bruce Willis [as Dr. Malcoma Croup]; Toni Colette [as Mrs. Seer]; Haley Joel Osment [as Cold Seer]; Casper the Friendly Ghost (cameo); Stretch (cameo); Stinky (cameo); Father Houlihan (cameo); Elvis Presley (cameo); Michael Keaton [as Beetlejuice] (cameo) |
| 6 | A Mad Look at Parking | comic story | 3 | script: Sergio Aragonés; pencils: Sergio Aragonés; inks: Sergio Aragonés | |
| 7 | Melvin & Jenkins' Guide to the Millennium | comic story | 2 | script: Desmond Devlin; pencils: Kevin Pope; inks: Kevin Pope | |
| 8 | - | comic story | 2 | script: Michael Gallagher; pencils: Peter Kuper; inks: Peter Kuper | |
| 9 | Mad’s 1999 Political Christmas Carols | comic story | 4 | script: Frank Jacobs; pencils: Paul Coker; inks: Paul Coker | |
| 10 | Mad's Celebrity Cause-Of-Death Betting Odds | illustration | 1 | script: Mike Snider; pencils: Hermann Mejía; inks: Hermann Mejía | Conan O’Brien |
| 11 | What Ball Are Many People Anxiously Waiting to See Finally Drop? | illustration | 1 | script: Al Jaffee; pencils: Al Jaffee; inks: Al Jaffee; colors: Al Jaffee | |
| 12 | Manic Y2K Panic | illustration | 1 | script: Tom Bunk; pencils: Tom Bunk; inks: Tom Bunk; colors: Tom Bunk | |