But conspiracy theorists are hard — correction: impossible — to appease. When the new Webdings font was introduced by Microsoft several years later, it only strengthened the convictions of those who believed hidden meanings were intentionally embedded in the software. And no wonder. Here's what "NYC" looks like in Webdings:

NYC  = 

How coincidental could that be?

The likeliest explanation I've come across speculates that the designers of Webdings, having learned from experience that people with too much time on their hands would hunt for secret messages, intentionally planted the rebus "I love New York" to taunt the inevitable conspiracy theorists.

The Doomsday Font

The even more bizarre notion that digitized fonts might actually be prophetic first gained currency in 1999, when doomsday predictions of all kinds abounded. Some clever wag discovered that typing out the word "MILLENNIUM" in Wingdings produces this result:

Disseminated to a doomsday-obsessed worldwide audience via the Internet, this nugget of trivia was soon being characterized as "eerie," "spooky," and "a weird coincidence" — which it most certainly was. As we know, all of the millennial doomsayers were ultimately proven wrong, but by then font folklore had already shifted away from conspiracy theories and into the arena of prophecy.

Which brings us, lastly, to "Q33NY," which we are now being told in email lore was the flight number of one of the airliners that crashed into the World Trade Center on September 11, 2001. In Wingdings it looks like this:

Obviously we're supposed to interpret this as a direct reference to the terrorist attack. It's all there — the airplane, the "twin towers" (okay, that's a stretch — they look like symbols for documents to me), a skull and crossbones (symbolizing death, of course) and the Star of David (evidently meant to represent anti-Israeli sentiments on the part of the hijackers).

There's just one problem: Neither of the airliners involved in the attack on the World Trade Center bore the number "Q33NY."  The actual flight numbers were as follows: American Airlines Flight 11 and United Airlines Flight 175. It's clear, then, that someone carefully fabricated the sequence of numbers and letters in the email to achieve the desired effect.

No "spooky prophecy" or "weird coincidence" there — just a hoax.

Further reading:

ADL: Internet Rumors About Microsoft Wingdings Are False
The Anti-Defamation League pooh-poohs current and past "urban myths" about the Wingdings font.