Unknown Armies has a published adventure titled "Fly to Heaven," in which an airplane is hijacked by a madman who plans to broadcast himself crashing the plane into the Sears Tower in order to ascend to the Invisible Clergy as the archetype of The Terrorist. Did we mention this was published in 1998?
One of the Shadowrun supplements from the 90s describes a volcanic eruption in Japan that triggers nuclear accidents at a cluster of fusion power plants, irradiating large areas of the island nation's densely-populated coastline. At the time, it read like WizKids backpedaling on the game-line's previous Japan Takes Over the World slant, but it's a lot darker of a Take That now...
The Vampire: The Requiem book "City of the Damned: New Orleans" has a moment that straddles the line between this and "Funny Aneurysm" Moment. A sidebar mentions that if you really want to shake up the political structure of New Orleans, then much of the city is below the water line... and given the Crapsack World nature, odds are those levees would go down with one strong hurricane, no doubt raining destruction on the city and wiping out many of the elder vampires. This book was published in 2004. Yeah.
Two cards from Illuminati: New World Order are very creepy after the 9/11 attacks. The Pentagon shows a mushroom cloud coming from the eponymous building. Terrorist Nuke shows a two-tower building that looks like the World Trade Center with an explosion near where the first plane hit.
Then there's one card for Princess Diana, which mentions she's immune to attacks from an enemies "Peaceful" and "Liberal" aligned groups... but not from "Media."
The GURPS supplement Super Scum featured a supervillain who'd turned to crime after being drummed out of college football for being a metahuman. He has the quirk "Idolizes O.J. Simpson". In the 1980s, of course, that could only be interpreted as a reference to Simpson's athletic career...
In 1972, British Petroleum released a board game titled Offshore Oil Strike. Set in Western Europe, four players explore for oil, build platforms and construct pipelines. The first player to earn $120 million wins. Players must deal with hazard cards, one of which reads "Blow-out! Rig damaged. Oil slick clean-up costs. Pay $1 million."