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Mad #389 January 2000
- Cover Artist: Drew Friedman
- The Supremos (TV Satire)
- The Mad 20 Dumbest People, Events and Things of 1999 (color section)
- 1. Y2K Panic
- 2. Hillary's Clinton Run For Senate
- 3. Teen Exploitation Flicks
- 4. Latin Music Mania
- 5. George W. Bush's Coke-Using Non-Denial Denials
- 6. Jerry Falwell Takes On Teletubbies
- 7. Around the Clock John F. Kennedy Jr. Crash Coverage
- 8. Cell Phones Everywhere
- 9. Sega Introduces the Dreamcast
- 10. Baseball Umpires Strike Out
- 11. The Blair Witch Project
- 12. Monika Lewinsky's Autobiography
- 13. Woodstock '99
- 14. Stock Market Frenzy
- 15. Beanie Babies Retirement
- 16. Random Acts of Senseless Violence
- 17. Tae-Bo Fitness Craze
- 18. List-O-Mania
- 19. Pamela Anderson's Breast Implants - Al Jaffee Fold-In
- 20. Jar-Jar Binks
- Spy vs. Spy -- Headphone Vice
- Melvin & Jenkins' Guide to the Millennium
- Monroe & Christmas
- 1999 Political Christmas Carols
- The Sick Sense (Movie Satire)
- Celebrity Cause-of-Death Betting Odds -- Featuring Conan O'Brien
- Sergio Aragones -- A MAD Look at Parking
- Duck Edwing -- Absurd Man of Alcatraz
- Al Jaffee Fold-In -- What ball are many people anxiously waiting to see finally drop?
- Back Cover -- A Monumental Disaster
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