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Mad #299 cover
Cover: Mort Drucker

Mad #299

Dec 1990 · EC · 1.75 USD
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★ 1st appearance — Edna Krabappel
About this Issue

Mad #299 (December 1990) holds a distinct place in both Mad history and the broader pop-culture record as the magazine's first full Simpsons-themed issue, appearing while The Simpsons was still in its debut season and 'Bart-mania' was sweeping American youth culture. By devoting multiple features — including the cover, a TV parody, a behind-the-scenes peek, and a spin-off gag piece — to a single property, it represented a notably concentrated editorial focus unusual for Mad at the time and signaled the arrival of a franchise that Simpsons producer Bill Oakley would later describe as Mad's spiritual successor for a new generation. The cover image of Alfred E. Neuman 'cutting' Bart Simpson's signature spiky hair, rendered by Mort Drucker, became one of the more remembered visual jokes of the era, directly acknowledged years later when Simpsons creator Matt Groening posed with the very issue at a comics convention.

Contains 19 stories
The Simpsons
2 pp · Humor, Satire-Parody
Homer SimpsonBart SimpsonGeorge BushRichard NixonJerry TarkanianGeorge SteinbrennerWilliam BennettMarge SimpsonAndrew Dice ClayLisa SimpsonMaggie SimpsonZsa Zsa GaborEva Gabor
A Mad Peek Behind the Scenes at "The Simpsons" Studio
2 pp · Humor, Satire-Parody
Marge SimpsonMaggie SimpsonLisa SimpsonMatt GroeningHomer SimpsonBart SimpsonNancy CartwrightDan Castellaneta
Using the Simpson Look to Update Stale Appearances
2 pp · Humor, Satire-Parody
Margaret ThatcherMikahil GorbachevCarly SimonDan QuayleMarilyn QuayleBarbara BushMike TysonDon KingYitzhak ShamirNew Kids on the Block
Mad Reviews the 21st Century Ahead of Time
3 pp · Humor
President QuaylePaul RodriguezNolan RyanCherDick ClarkSnoopy
The Nefarious Noose Nuisance
1 pp · Humor
Words and Phrases That Left the English Language During the 80's
2 pp · Humor
Spy vs. Spy
1 pp · Humor
The Black Spythe White Spy
Mad's Sports Business Agent of the Year
4 pp · Humor
Jock NicholsonJerky Kapsting
Mad Examines Some Cave Writings of Prehistoric Man
3 pp · Humor
The Zippy Zoo Zapper
1 pp · Humor
The Mad People Watcher's Guide to an Airport
3 pp · Humor
Totally Original Never-Been-Done Before Movie Plots
2 pp · Humor
The Lighter Side of...
5 pp · Humor
The Raging Rabble's Revenge
1 pp · Humor
World Communism Close-Out Sale
2 pp · Humor
Mikhail Gorbachev ["Crazy Gorby"]
The 9 Real Reasons Why Your Parents Won't Let You Have a Pet
2 pp · Humor
What Every American Should Be Required to Learn
2 pp · Humor
A Mad Look at Supermarkets
3 pp · Humor
Totally Recalled
4 pp · Humor, Satire-Parody
QuadHowitzerArnold

ComicBooks.com Value

Our Model is In Beta
Raw (VF) $9
CGC 9.8 · 1 in census $143
CGC 9.6 · 2 in census $66*
CGC 9.4 none in existence
CGC 9.2 · 1 in census $42*
CGC 9.0 none in existence
CGC 8.5 none in existence
Show all 10 grades
CGC 8.0 none in existence
CGC 7.5 none in existence
CGC 7.0 none in existence
CGC 6.5 · 1 in census $20*
* estimate — limited direct-sales data at this grade
Our model’s value — refined as new sales data arrives · CGC census counts shown where available

More listings for this title

ORIGINAL RETRO MAD Magazine Cartoon Bar Cafe Mancave Aust Special No.299 1990 $6.91
Related listings we couldn't confirm as this exact issue · 1 total · seen 6 days ago

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History

The issue was published in December 1990 by E.C. Publications under co-editors Nick Meglin and John Ficarra, who had taken over the editorial helm from Al Feldstein in 1985 and were in the process of refreshing the contributor roster. The Meglin-Ficarra era Mad operated out of its longtime 485 Madison Avenue offices and still ran on a roughly eight-times-a-year schedule, placing #299 squarely within that pre-advertising, ad-free format the magazine would not abandon until 2001. Bringing in a concentration of Simpsons content so early in that show's run reflected the editors' instinct for chasing breakout cultural phenomena — a hallmark of the Ficarra-Meglin approach.

Trivia · 7 facts

  • Cover depicts Alfred E. Neuman shearing off Bart Simpson's spiky hair — painted by Mort Drucker, Mad's most prolific media-parody artist and a contributor from 1956 through 2011.
  • The issue's lead TV parody, 'The Simpsons' (Name That Toon Dept.), was drawn by Angelo Torres and written by Stan Hart — Torres being Mad's go-to TV-satire illustrator from 1969 through 2005.
  • A second major Simpsons feature, 'A Mad Peek Behind the Scenes at The Simpsons Studio' (A Massive Bart Attack Dept.), was illustrated by Sam Viviano and written by Charlie Kadau.
  • A third Simpsons piece, 'Using the Simpson Look to Update Stale Appearances' (Our Features Presentation Dept.), was drawn by Greg Theakston and written by Stan Hart, making the issue a rare triple Simpsons showcase.
  • The issue's movie parody spoofed the 1990 Arnold Schwarzenegger blockbuster Total Recall under the title 'Totally Recalled,' with art by Mort Drucker and script by Dick DeBartolo.
  • Regular recurring features present include Spy vs. Spy (Joke & Dagger Dept.), The Lighter Side of…, and Al Jaffee's Mad Fold-In (on the topic of air travel).
  • Co-editors Nick Meglin and John Ficarra and publisher William M. Gaines are listed on the masthead; Simpsons creator Matt Groening was later photographed at a comics convention holding this specific issue alongside Mort Drucker (documented in Mad #352, December 1996).

Full credits

writer Don Edwing
artist, inker Bob Clarke
cover pencils Mort Drucker

Reprints

Reprinted in Mad Special [Mad Super Special] #102 (1995), Mad for Decades #[nn] (2007), Mad #13 (2020), Mad #28 (2022), Mad #32 (2023)

Key issues in Mad

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