It aired March 4, 2001.
spoiler
A plane gets hacked by gov g-men and remote controlled to fly into one of the twin towers. They narrowly avoid it and clip an antenna on the roof.
How the fuck? I'm stunned! Also, why is this not a regular part of 9/11 memes?
That's true; there were several depictions of the WTC being attacked in popular culture and the media before and around this time. Examples range form Boots Riley's album cover to cartoons (there was an incident in GI Joe or the Transformers IIRC).
What makes the Lone Gunmen instance stand out, to me, is a couple specific details that coincide with the real event and are unmatched by any other portrayal (that I'm aware of), namely, it:
Show creator Chris Carter developed a working relationship with the FBI during the production of the X-Files, which makes it plausible that someone spilled the beans to him about actual goings on.