* FunnyAneurysmMoment: In "Dave Barry's Guide to Guys" when discussing his fireworks-obsessed mechanic Ed:
--> "If those radical Muslim fundamentalist terrorists had Ed on their team back in 1992, the World Trade Center would now be referred to as the World Trade Pit."
** In ''Dave Barry's Only Travel Guide You'll Ever Need'', he tells a story about how he really angered his wife by driving past a roadside attraction that she wanted to see. He jokes that if she ever files for divorce, she'll probably bring that up. A couple years later, they did.
** In his 1996 book ''Dave Barry in Cyberspace'', he joked that buying the right computer and getting it to work is about as easy as building a makeshift nuclear reactor out of watch parts. As the world at large learned just two years later in 1998, [[https://en.wikipedia.org/wiki/David_Hahn David Hahn of Clinton Township, Michigan]] essentially did just that in 1994, although his nuclear reactor never reached critical mass.
* HilariousInHindsight: In a 1990 article about television ratings, he mentioned that if there was a program called "Eat Bugs For Money", everyone would watch it. Cue ''Series/FearFactor'' in 2001.
** "The worsening economy takes center stage in February, when, amid much fanfare, Congress passes, and President Bush signs, an ''economic stimulus package'' under which the federal government will give taxpayers back several hundred dollars apiece of their own money, the idea being that they will use this money to revive the U.S. economy by buying TV sets that were made in China. This will seem much more comical in the fall."
* NightmareFuel: "I'm holding his nose!" from ''Literature/TrickyBusiness''.
** Also, the [[http://www.vjbooks.com/v/vspfiles/photos/BARTALK01-2.jpg cover]] of ''Dave Barry Talks Back'' features a picture of him holding the disembodied head of what looks like [[CloningBlues another Dave Barry]], and they're making expressions of "comical surprise" at each other that look like [[Film/TheGrudge Toshio Saeki]] in full-on "meow" mode.
** His columns on 9/11, which are not funny in the slightest.
** He also wrote a column about seeing his father for the last time before he died. If you've read the column, there's no way your eyes are dry right now.
** His son was once in a pretty serious accident, causing Dave to write about all the times he's felt [[AdultFear the horror of wondering if his son was all right]]. Thankfully, Robert lived and is a healthy adult (and a father himself) today.