My original idea was to make the creature half worm, but decided an octopus would be more interesting.
I started by blocking the model with a reference of a fire hydrant, and expanded from there.
I added a slight tilt to the bottom of it to add a bit of liveliness to the character.
I created a chain rig by creating a skeleton parented to the chain links and then used an IK handle to curve it. Next, after modeling the tentacle, I rigged it to a linear skeleton controlled by a spline IK handle.
The goal of this project was to create a character by combining two completely unrelated things from real life. I tried a number of different approaches but I decided to pursue the idea of a Fire Hydrant - Octopus hybrid.