B-25 Bomber vs. Empire State Building
Before 9/11 there was 7/28. At 9:49 a.m., 28th of July 1945, Lt. Col. William Smith mistook the tallest man-made structure on the planet for nothing when he banked his B-25 bomber into it. The plane hit so hard that one engine shot all the way through the building, out the other side, and landed on the roof of another building the next block over. All died on board. RIP.