- Once filled MAD office water coolers with white wine
- Testified in front of the U.S. Senate in defense of the comic book industry in the 1950s.
- Started Mad Magazine in desperation after his successful EC Horror Comics were blacklisted by the U.S. Senate.
- When an issue of Mad Magazine had a raised middle finger on the cover, Gaines sent a personal apology to every person who wrote to complain about it.
- Once sent a vegetarian member of his staff out to buy hot dogs, because he knew for certain that the man would not eat them on the way back.
- A right-wing general once tried to get Mad magazine banned as "communist" and indecent literature. Gaines took the man to court, and then boasted to the reporters that if the judge addressed the man as "General", he would insist on being addressed as "Private First Class".
- In a parody of the Mad Magazine slogan "What? Me Worry?" the New York Daily News 1992 obituary headline for Gaines read: WHAT? ME DEAD.
- Founder and publisher of "Mad" magazine.
- Collected miniatures of the Statue of Liberty, and related items.
- Often ate at Little Charlie's Clam Bar.
- Huge fan of zeppelins.
- Always listed the company's attorney among Mad's staff in the magazine's roster, listing his department as "lawsuits".
- A noted gourmet, as well as a gourmand.
- While in the army he was permanently assigned to KP (Kitchen Patrol), which sparked his lifelong love of gourmet cooking.
- Paid generously for cartoons and articles, but he always bought all rights to the material. This meant that once he paid for it, it was his forever.
- He was both a staunch atheist and staunch Republican, which put him at odds with most of his employees. He once flew into a rage over a Mad magazine cover that depicted then-President George H.W. Bush setting fire to the Constitution.
- He was inducted into the Will Eisner Comics Hall of Fame in 1993.
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