A 1994 Iron Man episode "The Grim Reaper Wears a Teflon Coat" featured an attack on the Twin Towers & Pentagon

Seven years later, these buildings were actually attacked by terrorists on 9/11.

https://youtu.be/7BNsI9G1gEE

https://www.reddit.com/r/television/comments/pm5f1s/a_1994_iron_man_cartoon_episode_the_grim_reaper/