I have a few as well, but my most recent was from the current game I'm working on, a legacy. Toddler from gen. 4 who was close with his grandmother, happened to be in the room with her when she died. His dad (married into family but also close with mother-in-law) was also there with them. So they both watched her die while her 3 kids were at work. Then a few days later, while toddler's mom was pregnant, mom's aunt dies. So second child is born and dad invites his family over to meet baby. Well, his mom and his wife's mom (the one who died) happened to be good friends. Everyone was walking around all mopey even though the birth of a new baby should be happier... and they're all still sad.
And earlier on, during my first gen. I believe, at least 5-7 people that my sim knew all died. In real life, it was maybe 10 minutes passing. So in sim time, it was a couple a day. It was awful. Got to the point that I told my game (to no avail) to stop killing people for a bit. During gen. 3 I got a mod for more realistic reactions to deaths and has made the death of random acquaintances easier on my sims.
Edit: Here's the pic from the first story when they watched her die.
https://i.imgur.com/SkDUG1qm.png