I've seen planes that fly straight into buildings and explode, though I've neve had one drop on me. I did have one fly straight into a building in front of me, and when it hit the ground, the two occupants fell out and one of them dropped a bunch of money, SCORE!
Check this out for laughs though. I had just passed the Los Santos Forum 8 Track and was cruising around enjoying the Hotring Racer. I stopped and parked at the Commerce 24-7 and went to get on the bike to do the asset mission. I stopped and turned to look because I heard sirens and shooting, out towards the street. As I turned the camera view out to the street, a car being chased by a cop car turned to come into the parking lot and got hung up on the wall, with the back wheels off the ground. The cop stopped and got out of the car and started shooting at the car. The passenger of the car hangs out the window and starts shooting back, the driver continues to try to get the car dislodged from the wall. I kept on watching 'cause I wanted to see how this played out, it gets better. Soon the passenger killed the cop but more started showing up, and shooting back at the car. Eventually the car started to smoke from the engine, I knew it was almost over. All of a sudden the car got free from the wall and took off in a big circle around the parking lot, with the cops still shooting at it. Wouldn't you know the d#mn thing ran right into my car and blew up.