Kicking off this list we have perhaps the strangest pet that the Simpsons have ever adopted - well, maybe aside from that Screaming Caterpillar, but the less said about that the better.
Initially, Homer's plan was to bring Pinchy home so he could fatten him up for eating, ensuring that he would have the best lobster dinner possible. However, as time went on Homer found himself becoming emotionally attached to him. Even going so far as to make Pinchy an honourary member of the family, taking him along for walks on the beach and other such wholesome activities - much to the chagrin of both his family and others.
Sadly Homer's brief foray into owning a lobster came to a very tragic end when he decided to give Pinchy a nice hot bath after he got dirty chasing birds in the backyard. In typical Homer fashion though, he made the bathwater far too hot and ended up boiling poor Pinchy alive.
Homer's visible anguish and grief at the loss of his beloved pet lobster should be one of the show's most heart-wrenching moments, but it's beautifully undercut by the sight of Homer devouring the poor critter's corpse whilst sobbing uncontrollably.