The influence of Ray Harryhausen and Voyage to the Bottom of the Sea kindled a fascination with squid and octopus type creatures as a kid. Movies like Trollenberg Terror and It Came from Beneath the Sea with their tentacled behemoths were my favourite. As a result, I collected octopi-like monsters. One of the earliest is the rubber Octopus above, a find from Chester Zoo around about 1969. He's been through the wars, losing the end of a tentacle and suffering a head injury from a dog bite, but he's holding it together well!
Next up is the much more recent Fisher Price Octopus from the Submarine playset, made from wonderful translucent and flexible plastic, he's much more accurately moulded, down to a round beak underneath.
All of the toys are displayed with the Matchbox Jurrassic Park Diving Bell Sub, a neat little model from the Fallen Kingdom franchise.