Editorial
- Cover Artist: Drew Friedman
Featured characters
Table of Contents
The MAD 20 Dumbest People, Events and Things of...
1. Y2K Panic
Artist: Tom Bunk
2. Hillary Clinton's World (Andrew Wyath's Christina's World painting parody)
Artist: Richard Williams
3. Teen Exploitation Flicks - "Movie Title Graffiti"
Writer: Russ Cooper
4. Livin' La Vida Overrated "When Other Artists Jump on the Latin Music Craze"
Artist: Hermann Mejia
5. George W. Bush's Snow Job - "got coke?" (got milk? ad parody)
Photographer: Irving Schild
6. Jerry Falwell Takes On Tinky-Winky - "Televangelist-Tubbies"
Writer: Charlie Kadau Artist: Jack Syracuse
7. Around the Clock John F. Kennedy Jr. Crash Coverage (People magazine cover parody)
Writer: Joe Raiola Writer: David Shayne
8. America's Hang Up With Cell Phones - "The Talker" - (Rodin's The Thinker parody)
9. Sega Introduces the Dreamcast - "Buy 'R' Toys" - (Toys 'R' Us ad parody)
Artist: Scott Bricher Writer: Scott Maiko
10. The Umpires Strike Out - "Taken Out of the Ball Game" - (Take Me Out to the Ball Game song parody)
Writer: Desmond Devlin Artist: Keith Seidel
11. The Blair Witch Project - "Eerie Comparisons Between The Wizard of Oz and The Blair Witch Project"
Writer: Desmond Devlin Artist: Sam Sisco
12. Monica Tells All - "Phrases That We Knew Would Never Appear in Monica Lewinski's Autobiography"
Photographer: Irving Schild Writer: Jeff Kruse
13. Woodstock '99 - "3 Days of Pricey Mayhem" - (3 Days of Peace & Music poster parody)
Writer: Scott Maiko
14. Stock Market Frenzy - "A Typical Investment Ad For Suckers (Like You!)"
Writer: Dick DeBartolo Writer: Jim Johnstone Artist: George Woodbridge
15. Beanie Babies Call It Quits... Yeah, Right! - "The Telltale Signs of Post-Beanie Syndrome"
Writer: Desmond Devlin Artist: Lisa Haney
16. Random Acts of Senseless Violence - "A Bumper Sticker We're Sure to See"
Photographer: Irving Schild Writer: Michael Gallagher
17. Tae-Bo Fitness For Fools - "Tie-Blo" (ad parody)
Photographer: Irving Schild Writer: Mike Snider
18. List-O-Mania! - "12 Stupid Lists You May Have Missed"
Writer: Tom Stern
19. Pamela Anderson's Breast Implants - Fold-In
Artist, Writer: Al Jaffee
20. Jar-Jar Binks - "A Movie Poster We'd All Like to See"
Artist: Roberto Parada
Melvin & Jenkins' Guide to the Millennium
Department: The Schmuck Stops Here
Writer: Desmond Devlin Artist: Kevin Pope
Mad's 1999 Political Christmas Carols
Department: Oh Little Town of Washington
Artist: Paul Coker, Jr. Writer: Frank Jacobs
Mad's Celebrity Cause-Of-Death Betting Odds: Conan O'Brien
Department: Grieving Las Vegas
Artist: Hermann Mejia Writer: Mike Snider
Back Cover Inside: What ball are many people anxiously waiting to see finally drop?
Artist, Writer: Al Jaffee